In my itinerary below, I will talk about my experience of visiting Maderia in December and why it will not give you the full island experience that you are probably expecting. While I am not trying to discourage you 100% from visiting during that time, I hope my experience will better prepare you compared to what I was expecting. If I knew what I’d see and what I’d miss out on, I’d plan my itinerary totally differently than how I did. That’s what I hope to give you with this post, an off–season-optimized Madeira itinerary. To compare, a couple of years back, I visited Madeira’s southern neighbor Tenerife, during a similar time. My off-season vacation there was much better in terms of weather even though geographically, these two islands are pretty close.

While this itinerary tells you additional information about traveling to Madeira off-season, you can use it all year round to plan your travels too.

At the end of the post, you can download this guide as well as a map for your travels.

Traveling to Lisbon as well? Don’t forget to check out my Lisbon guide!

Madeira Logistics

Best time to visit Madeira

Let me just cut to the chase and tell you that if you want to experience all of Madeira, off-season time considered between November and April, might not be the best choice. Despite a lot of resources telling you that Madeira could be a year-round destination, I would argue otherwise. By visiting between May to late September, you’re maximizing your chances for clear skies and good temperatures.

There are some pros, however, to visiting during the off-season as I did. You will save on flights, accommodation, and car rental and you’ll avoid the crowds that come with the vacation season in Maderia. Although most attractions won’t be closed you might not be able to see everything, especially if the weather isn’t great.

Suggested length of stay

How long you will stay depends on what you’d like to do there. For example, some hikes can take an entire day, and there are multiple that people put on their Madeira itinerary. Again, when traveling off-season, you will not be able to check everything off your Madeira bucket list so 3-5 days is a decent time frame. In season, I’d say an absolute minimum of 4 days is needed to see everything, with 5-6 being more ideal for a short trip.

Traveling to Madeira

Flights to Funchal

Getting to Maderia is pretty easy with frequent flights from Lisbon and a couple of other European airports. I even saw one direct flight from NYC flying out once per week! I like breaking up my flights rather than automatically searching between origin and destination, meaning if I’m flying from NYC, I will search NYC to Lisbon and then Lisbon to Madeira. I compare my times with layovers and frequently find better deals, instead if I were to search NYC to Madeira in one shot. A round trip for the very end of November cost me under $450 for both flights. Although I’m here to argue that off-season travel isn’t ideal here, if you’re on a budget, Madeira in December might be a great money saver!

Getting around – Car rental in Maderia

Madeira is a small island and you can drive from one end to the other in a couple of hours. North to South is even faster. Seeing the whole island is indeed possible during a Madeira 5-day itinerary.

When other travelers pointed out that driving in Madeira is an adventure in itself, I didn’t quite believe it. I drove in tricky conditions and places but driving there will get its own category in my personal driving experiences. Before my trip, one of my friends said, “If it doesn’t look like a road in Madeira, it probably is” and looking back at this, that was an extremely accurate description of driving there. Most roads in Madeira are freeways and tunnels but once you venture into towns, one-way roads will magically fit two cars and 30-degree hill roads will become the norm.

I don’t want to discourage you from renting a car there but rather prepare you for what to expect. Renting a car is the absolute best way to see the island and it will save you a ton of time on sightseeing. I normally book through Rental Cars but I found a better deal on Holiday Autos. While I am a creature of habit and don’t trust new websites on deals, I had a very smooth experience will them and will rent in the future. For your reference, an automatic car rental in Maderia during the off-season cost me ~$250 for 5 days using Rodavante with car pick up and return right at the airport. A manual rental is much cheaper but unless you drive it regularly, I would not get one there.

Although driving there was certainly a challenge, I wouldn’t have done it any other way. If you’re planning to do mountain driving, watch for an automatic car’s brakes as they might start smelling, especially in wet conditions.

Where to stay in Madeira

Where you stay during your Madeira vacation depends on what you want to do. If you’re unsure, Funchal is the main city and can be a good base for taking drives throughout the island. If hiking is your main priority, consider staying in the mountains instead. Most importantly though, if you have a car, it’s fairly easy to see all nooks of the island no matter where you stay. Maderia has a ton of hotels, some hostels, and even more Airbnbs. Which you choose should depend on your personal preference. While Airbnb has its own issues, especially in bigger cities, I felt that renting one in Madeira where I was in communication with the hosts directly was the way Airbnb originally intended the platform to be.

Airbnb in Madeira

Traveling with my parents, we opted for two Airbnb in Maderia because we wanted a comfortable base for exploring. I spent a lot of time searching for the perfect combo of what we were looking for and I think I hit the jackpot with both of them. The first Airbnb located 7 min from the airport, was the entire first floor of a large house overlooking the ocean, with a beautiful pool and a walkway to the beach promenade. One of the downsides of traveling to Madeira off-season is that we didn’t get to use the pool or spend time in stunning outside space as much. As a bonus, the coolest part was watching the planes land at the nearby airport right from my bedroom.

The second Airbnb that we rented in Madeira was located near Sao Vincente. It was a huge home in the mountains with sick views and the best host I have ever experienced throughout my years of traveling. I loved having two locations, one with the ocean view and the other with the mountain one but for someone who doesn’t want to move between two locations, this might not be the best option. If you’re interested in booking either of these locations, send me an email and I’ll be happy to share the link.

What to pack for Madeira in December

Ok, I am only including this section because I packed like an idiot for this trip. Let me explain. A couple of years back, I traveled to Tenerife during a similar time of the year. I falsely assumed that the two destinations would have similar weather and that packing 5 dresses for each day would be the way to go. My outfits consisted of light athleisure, dresses, and a couple of cute outfits for the barn (shoutout to those who get the reference). I ended up wearing two heavier sweaters and the jacket that I packed for the plane for pretty much the entire time I was there. These are the items not to forget when you travel to Madeira during the off-season:

• A rainproof jacket and/or umbrella – The rain won’t last long but when it comes around, you want to have a raincoat on hand instead of looking for a place to hide.
• Light coat or cardigan – During the day, while you won’t need a heavy coat, it will get chilly when the sun is not out.
• Waterproof shoes – If hiking is on your list to do or if you want to check out the Fanal Pond, then sneakers won’t be sufficient. The ground is wet and puddly so good outdoor shoes that won’t soak are a must.
• (Bathing suit) – I saw a couple of brave souls swimming in the chilly waters of Porto Moniz pools, if you like cold swims, don’t forget to pack a suit.

People & Safety

Overall, I’d say that most locals in Madeira were really nice. My Portuguese is non-existent but I tried to use my hello/please and thank yous whenever I could. Side note, do not use Spanish in Madeira or in any of Portugal, it is not Portuguese and it’s a faux-pas there. For the most part, the experience was very positive. In terms of safety, Madeira is a very safe destination. Some common travel scams to watch out for include the following:

• Taxi scam – This isn’t so much a Madeira scam but rather a worldwide one where dishonest taxi drivers charge you ridiculous amounts for short rides. Always demand the meter to be turned on to avoid this. It has been reported to happen in Funchal on some travel forums.
• Market fruit sample – When you go to Funchal, one of the main attractions in town is Mercado dos Lavradores. It’s a cute and colorful market filled with merchants offering you fruit samples. However, a lot of the fruit is enhanced with syrup and when you taste it, you’ll naturally want to purchase some for later. The fruit will cost you an insane amount and when you get home, it will not have the same taste as that first bite you had at the market. We bought fruit in Funchal, a couple of streets away from the market but I still got ripped off. While not a true scam, just be aware of this little selling trick.

WARNING! TRAVEL SCAM IN MADEIRA

Restaurant bill additions – As a former waitress/bartender, I’d like to think that my bullshit meter is pretty good when it comes to other waiters. I could easily tell when you’re actually in the weeds or if you’re just being lazy, because hey, I’ve done the same shit 🙂

What I always make sure to do though is check the itemized bill no matter where I’m dining. During busy moments, it is genuinely possible to make a mistake and charge extra or add a wrong item. However, when your bill magically increases by 100 euros, you know something is up. This was the case at Taberna, a small highly rated restaurant in Santa Cruz. While the nice waiter chatted with my family all dinner, when the bill came, suddenly he started rushing us with the credit card machine. That triggered a red light in my head and I asked to see the itemized bill before blindly swiping my card. Our small appetizers and a couple of drinks added to over 130 euros. I noticed that one 10 euro app was charged 10 times on the bill, a small trick that made the bill look legitimate.

Now, if I wasn’t a waitress in my past life, I would buy the story that this was an honest mistake. However, when I brought up the price discrepancy to the waiter, he quickly looked at it and said, “Oops, silly me” and didn’t apologize or display any sort of remorse for what had happened. The fact that he was quick to run to us with the credit card machine was also sus. I heard about this scam in cities like Rome or even in Lisbon but I never assumed it would happen in Maderia. So despite the food being tasty and the restaurant being super cozy, don’t assume it won’t happen even in less touristy parts of any town.

Food and Drinks to try in Madeira

Out of the entire time I spent on the island and the numerous meals I ate, I only had one mediocre meal and tbh at my own fault. The lesson I fail to learn over and over is never to order pizza outside New York or New Jersey or Italy of course. Back to Madeira food though, it is so so tasty and actually extremely affordable. Here are my top picks for food to try in Madeira:

• Prego sandwich: This is the most amazing sandwich I had in my entire life. I’m serious, nothing compares. You can get it almost anywhere. It’s a steak sandwich on buttery and garlicky bread that comes in a couple of variations.
• Espetada: A long skewer of hanging meat. Its simplicity makes it super tasty.
• Espada or black scabbard fish: This was my mom’s favorite, it is usually served with bananas. This is one weird looking creature but it tastes delicious!
• Bolo de molo de mel: This traditional honey cake is pretty tasty!
• Madeira Wine: It’s heavy and has a very distinct taste and you’ll certainly feel it going down your throat! Blandy’s Madeira is a very popular spot to consume this beverage.
• Poncha: Poncha is the most delicious alcoholic drink. It’s made of cane rum and had different fruit flavor options. Get the traditional kind and enjoy the happiness that comes after drinking this 🙂

For more interesting food finds, I used Brogan Abroad’s guide before traveling to Madeira for the tastiest food finds!

Random Useful Tips for Madeira Travel

• If the weather is acting up during your visit, check the live cams! I used these to see whether mountain peaks were clear from clouds or where I could find the sun on the island.
• Miradouros are viewpoint spots all throughout the island. Some are simple pull-over style along the highway, others require short walks to reach the spot. My advice is to stop at all of them 🙂
• When visiting Tenerife which has similar viewpoint parking areas as Madeira, my car window got smashed and all my belongings got stolen during that trip a couple of years back. When you leave your car anywhere, take everything with you. Even small stops that seem safe can be targets for petty theft.

Things to do in Madeira

In terms of the number of things to see in Madeira, I’d say you can stay pretty busy during your trip. The majority of the attractions throughout the island include outdoor activities. One of the most important things to consider when traveling off-season is how important certain attractions are to you. If you need a dense itinerary with lots of outdoor attractions, consider in-season travel. Instead, if you need a simple getaway with a couple of things to do here and there, the off-season is probably a better choice.

Below, I bring you a 5-day Madeira itinerary that also gives you an off-season expectation. However, you can use my travel plan for any time of the year. Since Madeira is a small island, for the most part, it doesn’t matter which order you do the days in. However, note that the first two days are optimized for the Funchal area and the remaining for the other parts of the island.

5-day Madeira Itinerary

At the bottom of this post, you can download this travel guide to Madeira to bring along on your trip. Additionally, you will find a map of all the attractions so you don’t have to worry about saving them yourself.

Day 0

We’ll call your arrival day, Day 0. Arriving at Madeira airport (Ronaldo Cristiano Airport 🙂 ) can be quite the experience on a windy day. If you’re a nervous flyer, I wouldn’t YouTube any videos of landings there. However, despite its windy challenges, there only has been one accident in the late 1970s. Since then, the runway has been extended and only experienced pilots are allowed to approach a landing there.

The airport is on the east side of the island and is located a short ~25 min drive from Funchal. When you get off the plane, have all your paperwork ready as you’ll be asked for your Madeira Safe bar code. If you’re renting a car (which I highly recommend), the pick-up process once you land is super easy, my checkout took under 10 mins. The rental car lot is located across the street and you should be on your way within a short time of arrival. If you require public transportation, here is a helpful official link.

Flights arrive all day long so the timing of your Day 0 will depend on where you’re coming from. I personally arrived around 8 pm but my Airbnb was located 7 mins away from the airport so I was “home” very quickly. Note that restaurants and stores aren’t open too late so if you are planning a later arrival, make sure to eat before your flight.

Day 1 – Southern Part of Madeira

Valley of the Nuns

Now that you settled in, there is no better place to start your vacation than by seeing Curral das Freiras or Valley of Nuns in Madeira. It’s located a short drive from Funchal and it’s an in/out kinda trip. This small town has a couple of restaurants and tourist shops but aside from the views, there isn’t much to do there. However, these viewpoints are crazy beautiful and you shouldn’t skip this area on your Madeira adventure.

There are two major viewpoints, the first being Eira do Serrado, a very popular spot on the island. Once you arrive at the spot, there is a small parking spot with a café. In order to get to the viewpoint, you’ll have to take a short 5 min walk. I recommend grabbing a coffee and a pastel de nata at the cafe for a little longer appreciation of the area. The second point, Paredão Viewpoint, is located above the clouds and it’s not too far from the first one. It’s also a short walk from the parking area.

After admiring the views from the top, I recommend grabbing lunch in the little town which will give you a slightly different perspective of the area. Everyone recommends a restaurant called Sabores de Curral but I opted for La Perla instead. I was extremely impressed with the food but the views along with a cold beer made it even more delicious.

Off-season struggles: The area gets mixed weather during the off-season but the good news is that if it starts raining, the clouds will most likely pass. Pack an umbrella or a rain jacket. We waited out the rain having a coffee and then got rewarded with a beautiful rainbow!

Funchal

For the second part of the day, visiting Funchal will give you the exact opposite vibes from your nature-filled morning. Funchal is the capital of Madeira and is certainly worth spending some time in. If you’re driving in, the streets can get really narrow so rather than looking for street parking, I recommend finding a parking garage near the center. Garage prices are very cheap and it will save you time and a headache.

I would simply recommend walking around Zona Velha, seeing the market, and most important feeling the liveliness of the town by spending some time by the waterfront. Don’t forget a mandatory stop for some good poncha either. Note that I am not including the botanical gardens just yet. Funchal is safe but make sure to watch your belongings for pickpockets. Here are some known attractions in the city for you to check out:

• Mercado Lavaradores: Yes it is a tourist trap but hear me out for a second. The market has really pretty colors and cute souvenirs to look at. I certainly wouldn’t buy fruit here (read my scam warning above) but I do like browsing through places like these.
• Avenida Arriaga: Right next to the market, you will find this shopping street with a lot of tourists. It’s a good spot to take a stroll and window shop for a bit.
• Zona Velha: This is the Old Town part of town which includes cobblestone streets, restaurants, bars and lively nightlife.
• Cathedral of Funchal: A pretty local catholic church right in the heart of town.
• Praça do Povo & Funchal Marina: Walk along the waterfront to catch the nice atmosphere of locals and tourists. When I visited in late 2021, that area had a cute little town fair with rides.
• Parque de Santa Catarina: Cute little park with views of the town and the incoming ships.
• Cristiano Ronaldo Statue: If you make your way by the park, grab a photo with the icon of Madeira, the one and only Cristiano Ronaldo. Since he was born on the island, you will see a lot of references to him. There is even a museum 🙂

Make sure to stop at Rei da Poncha, a very popular hole in the wall with some great tasting poncha and some great snacks too. The outdoor tables might be full but just linger around for a couple of minutes and a table will free up in no time.

Off-season struggles: Day one of your Maderia travel will actually work in your favor if you’re traveling off-season. Funchal won’t be too crowded with people and if you’re visiting in late November or December you will get to see fun holiday decor. The southern part of the island is usually sunny and even if it rains, the rain should pass by quickly. Places like Rei da Poncha won’t have a line and you won’t be annoyed with the crowds.

Day 2

(Pico do Arieiro)

Pico do Arierio was one of the most anticipated spots I wanted to see in Madeira. A simple google search will show you why. It’s the third-highest peak and one of the only that you don’t actually have to hike. Yes, you can simply drive there and see the most amazing views without any pain 🙂

I wanted to see the incredible sunrise overlooking Madeira under the clouds. However, we attempted this sunrise once in person and then checked the webcams for both, sunrise and sunset for the entire time we were there and were not able to successfully see this spot. One of the biggest risks you take with traveling off-season is missing amazing spots like this one. I’m including this on Day 2 because you might have to attempt to see it multiple times during your trip.

However, if you’re traveling in season, you have to check this couple’s guide to visit Pico Arieiro and actually all their Maderia guides which are extremely detailed and resourceful. There is a very popular day hike from Pico Arieiro to Pico Ruvio and I recommend that blog to give you the best details on it.

Back to Funchal

While the first day in Funchal consisted of exploring the basics of the city, I did don’t want to include the botanical gardens then, as the whole experience would have been very rushed. So for day two, you can explore either Monte Palace or Madeira Botanical Gardens (or maybe even both if you love gardens). I personally only visited Monte Palace and it was a super beautiful place that I’ll recommend to you.

Here is some info on them:

• Monte Palace – An additional attraction to this place is the fact that you can take a cable car from Funchal on the Funchal – Monte line to get here scoring some awesome views from above of the city. A one-way ticket is 11 euros and a roundtrip is 16. Their Japanese-style gardens were stunning and I had a great time taking random turns and not following the map per se. We spend about 3 hours exploring which included a stop at the gift shop for some complimentary Madeira wine tasting. To get back to Funchal you can simply take a cable car back or take a ride in the famous Toboggan cart ride. It was a little too touristy for me but people swear this is a fun activity.
• Botanical Gardens – The second gardens are located not too far from Monte Palace and are connected by the Botanical – Monte line in case you wanted to take the cable car again. I haven’t visited these gardens but people often prefer Monte over this location.

Cabo Girão Skywalk

After exploring the gardens, take a short ride to the famous glass skywalk with great ocean and Funchal views. To be honest I expected a much bigger platform however it was still pretty impressive. There is no entrance fee and the spot gets pretty crowded. One thing that I loved more than the views was the strong eucalyptus scent from all the trees as you walk around. There is a small cafe with overpriced food and drinks on site but I recommend stopping there for a little break to enjoy the view even more.

Options for the afternoon

Personally, this is where I would take a little break and head back to my hotel and Airbnb to relax. Sometimes I tend to overlook how important relaxing is during vacation 🙂 However, if you’d like to continue with your day two activities, here are some ideas for the afternoon:

• Vinhos Barbeito: I found a nice family-owned winery near Funchal. It has great reviews and I imagine the wine tastes really good! Madeira wine is special within itself so why not drink it from someone that knows what they’re doing.
• Ribeira Brava: Explore this cute little town with shops, restaurants and nice mountain and ocean views. Beaches in Madeira are located all over the island but I actually found people swimming in this one off-season as the sun likes this place no matter what the month.
• Funchal at night: Local cuisine is bomb. So make sure to take yourself to a nice place, have some good traditional food and then walk around the town at night. Most towns should always be seen during the day and night. There is a whole new vibe that emerges when the lights dim!

Day 3 – Sao Lourenco toward Sao Vincente

For Day 3 of your awesome Madeira adventure, I recommend heading to the northern part of the island. Now that you got to see most of the Funchal area and its surrounding gems, it’s time to head to the super green part of the island. The one thing to note when you’re traveling to Madeira off-season is that the weather in the northern part is almost always more cloudy and wet compared to the southern part. This is what will make the biggest distinction between traveling in the off-months compared to peak season.

Ponta de São Lourenço

This awesome hike is certainly not a hidden gem of the island. If possible try to arrive before 10 am as the spot gets pretty crowded. Even better if you can make a sunrise hike! If you’re worried about weather conditions, don’t forget to check out the webcams.

This hike starts at the parking trail and goes all the way to the tippy top of Madeira. You won’t be able to reach the very end of these crazy rock formations because the very last part is separated by the ocean. The hike should take you between 1.5 to 2.5 hours each way depending on how many times you take picture stops. Towards the end, you will find a small cafe where you can use the bathroom or grab a coffee. This is a very popular part of the island so expect some crowds.

For a very detailed plan for this hike, I found this blog which does an excellent job of preparing you for it.

Off-season struggles: The weather is not going to be your best friend here. It might get more chilly and windy in the months of November and December. However, since peaks might not even be doable during that time, this is one of the few chances you have to experience Madeira’s nature.

Northern Drive Toward Sao Vincente

After the hike, you won’t probably want to do any more walking so I recommend a scenic drive along the northeastern part of the island. Here are a couple of stops to consider. Depending on the timing of your morning, you will not be able to do all of them so check out my photos below to see which ones you think you’d like best:

• Coastal Viewpoints – choose one:
  • Faial Beach: This little beach is located about 25 minutes from Sao Lourenco parking lot. I found it on accident while driving in that area. I wouldn’t swim there per say but the landscape is really nice! Off-season you probably won’t see another soul there!
  • Miradouro do Guindaste: Right above Faial Beach, there is a nice coastal viewpoint offering the awesome view the beach does but from slightly above. I’d say do one or the other since the views will be very similar.
  • Miradouro do Curtado: This one is located a short 10 min drive from the point mentioned before. It offers a nice view of local town as well as the northern coast nearby.
• Santana Houses: This was the most crowded place I encountered on my off-season trip to Madeira. Why you ask? I have no clue because as cute as the Santana Houses are unless you have some sort of historical curiosity about them, there really isn’t that much to see there. I don’t know what I expected but certainly not what I saw. I’d say you can pass this location if touristy places bother you.
• Hotel & Restaurante Quinta do Furão: This is a good place for an early dinner but before you head to the restaurant, go on a little walk around the property. There is a vineyard in the back and a garden in that is accessible to walk around patrons and it was a (hidden) place during out little drive. It’s super pretty and you can even catch a view of a waterfall from there.
• Miradouro da Beira da Quinta: Super quick stop but nonetheless a nice viewpoint of the local area.
• Sao Vincente: This is a small town that’s the base of a lot of northern hikes for people. We stayed at an Airbnb for the second part of our trip here and loved the quiet atmosphere and more local vibe compared to Funchal. The small town has a couple of restaurants and bars by the water. If you’re not staying in the area, I’d recommend grabbing some food before heading back home. I ate at Restaurante Calamar which had delicious food for amazing prices and Poncha de Sao Vincente, a local bar with awesome apps.

Off-season struggles: The northern part of the island is the rainiest and most cloudy off-season. Consider that when packing clothes for your exploration there. All the spots I mentioned above were cloudy and chilly when I visited. Comparing photos of them in the sun from other travel blogs, I certainly feel like I didn’t get the proper experience of them.

Day 4

Drive toward Porto Moniz

Before you head to see the famous swimming pools of Porto Moniz, there is a couple of quick stops you can make before heading over.

• Miradouro do Véu da Noiva: This is a very popular viewpoint on the island and while I think it was cute, I didn’t find it as fascinating as others have described. The main highlight of this stop is a waterfall that drops into the ocean but since it is pretty far and the road to access it is closed, it’s just a small stop. There is a gift shop there but it was very pricey compared to others I’ve seen.
• Seixal: What many describe as the best beach in Madeira is located in Seixal, a small town on the northern coast. It’s all black sand contrasting with vibrant green nature and surrounded by mountains. There are also small natural swimming pools located in town. While during off-season travel you won’t be able to swim, it’s worth visiting for the picturesque views.

Porto Moniz

The Porto Moniz natural swimming pools are swimming areas formed by lava and filled with fresh seawater on the northwestern side of the island. They are one of the coolest outdoor swimming pools I have seen. I hate to break it to you this early in the description but unless you like cold swimming, traveling during the off-season will unfortunately not allow you to fully enjoy them. I was super upset that I wasn’t able to swim in them, after naively reading some online comments claiming that late November is sometimes ok for swimming.

There are two pool areas in town. One with an entrance fee but only 1.5 euros, there you will find lockers and snack bars the other is free but more rocky and natural. The actual town is super small, you can walk from one pool area to the other in under 10 mins. However, my friends, I do not think you should skip visiting the town even without swimming. It is indeed impressive to see them and take some pictures in the area. I recommend making a stop in Porto Moniz for lunch or a drink.

Fanal Forest

Quick Tip: If you’re heading to Fanal Forest or Fanal Pond from Porto Moniz, make an easy and quick stop at Miradouro da Eira da Achada for more island views from above.

Fanal Forest is the one place that should work in your favor during off-season travel. Why? Because people love this place for a mystical experience of the fog and creepy vibes. If you visit during the summer peak months, the chances of the fog are said to be greatest in the morning. However, in the “winter” months, you can catch it at pretty much any time. Simply put Fanal Pond in your GPS and you will arrive in a small parking lot, then walk towards the forest. I recommend packing waterproof shoes and a waterproof jacket if you’re planning to walk around. I got soaked and cold while exploring and it wasn’t too pleasant. Overall it’s a cool place to visit for some awesome pictures. Put a pin in your map as the further you walk in the fog, the more likely you are to get lost.

There are many cows in that forest so be careful not to step in some cow poo as you’re taking your picture 🙂

Day 5

If you followed my itinerary, by day 5 you’ve seen top places that Madeira is known for. For this last day, I will give you options of things to do that are worth seeing on this stunning island depending on what you like to do.

Hikes & Levada Walks

Madeira is known for many hiking trails and Levada walks. I’m more of a drive-to-a-peak kinda gal unless I’m feeling inspired to hike as I did in Poland this summer (You can read my guest post on We Are Travel Girls about my super awesome hike in the Tatra Mountains). I did not hike in Madeira therefore I cannot give you solid advice on it. However, I found this amazing and super informative post from Claire on her blog and I recommend you follow her for the best hiking advice.

Small things to do in Madeira on the western side of the island

The western side is not as touristy as the other side of the island but that doesn’t mean if you should skip it. Although there aren’t as many attractions, here are a couple of spots to visit there:

• Garganta Funda Viewpoint: Although you will need to walk about 15 minutes to reach this viewpoint, the awesome waterfall that you will see at the end will make it worth it. The nice thing about traveling off-season is that you’re likely to see it in full action compared to the summer when it dries up. I regret not seeing this place during my visit.
• Ponta do Pargo Lighthouse: A small picturesque lighthouse on the far end of the island. It might not be a super exciting spot, but you can take a small walk in the area and admire the calm atmosphere.
• Cascata dos Anjos: The famous waterfall that falls on your car as your drive on ER101 is certainly a cool experience. If you’re driving toward the west side, you can even pull over and see it up close.

Speaking of the western side …

There is a less-known thing you do on the western side which is Achadas da Cruz cable car bringing you in the (almost) empty small local village. It’s an area only accessible by cable car (between 8 am to 6 pm) or a super steep trail. Not many (if any) locals stay there full time, it’s more of a nature getaway for them. For you, it means exploring two remote villages with stunning surrounding nature. I found a very detailed and informative guide on this hidden Madeiran location. Journey Era gives you more than enough detail about this place, he even takes the hike back up the hill in the evening.

Madeira Beaches

Although you won’t be able to comfortably swim in the ocean if you’re traveling off-season, or if you like cold water, spending some time near the beach even at a local cafe or bar is really nice.

• Calheta Beach has white imported sand and gives some nice tropical vibes. There are some all-inclusive hotels in the area too.
• Seixal Black Sand Beach: I mentioned this beach earlier but if you like black sand vibes, you should spend some time enjoying the beauty of Seixal.
• Ponta do Sol Beach: In the (almost always) sunny part of Madeira, you can find a nice small beach to enjoy without the crowds.

Porto Santo

If you’d like to do something more unique, take a day trip to Porto Santo, a small island located a 2-hour ferry ride away or even a short plane ride. There are daily morning departures with evening returns. Some people recommend spending more than a day there, while others do a day trip and are content. Here are two contrasting opinions, a day trip one, and a longer excursion. Hopefully, this lets you decide whether a day trip is worth it for you. Nonetheless, Porto Santo is a stunning destination that could be added as a bonus if you’re already in the area 🙂

Madeira Tours

If organized tours are something you enjoy, consider booking one in Madeira. Some of the more popular choices include dolphin/whale watching boat trips, jeep tours through the island, or even organized hikes. While these are not something I would opt-in to do in Madeira, as the majority of the things can be done solo, a lot of people enjoy having a pre-planned day.

While short excursions are not my thing, I personally always recommend food tours through which not only can you learn about the local cuisine, but see the area, learn history and interact with other like-minded people. I found a highly-rated tour, Madeira Food on Foot which offers different tours and even pre-made picnic baskets. I’d say that’s the best Madeira tour there is 🙂

Download this Madeira guide

Here is a free downloadable guide for you of all the places I talked about above. It’s a pocket version so I recommend reading everything above before downloading the guide for your travels 🙂

Download It HERE

Map of Madeira

Final thoughts on things to do in Madeira in December or any other off-season month

As promised at the start of the post, I tried to give you a realistic expectation of Madeira off-season. I’d say that I romanticized it too much and imagined that I could do more than I did even in the “winter” months.

To recap, here are the cons of things to do in Madeira during off-season times:

• Higher chance of poor weather: The rain and clouds will limit what you can see and do. What you imagine to be a sunny afternoon hike or a beach day will turn into hiding in cafes until the rain passes.
• Not seeing the best sunrise and sunset spots: The chances of having a clear sky up in the mountains which would normally give you out-of-this-world sunrises and sunsets are very slim. For 5/5 days of travel, there wasn’t a single day that we were able to see any peaks. I anxiously kept checking weather cams and even drove to two spots to check myself and I was not successful of seeing either of them.
• Natural Lava Pools: Despite having lava in its name, the swimming pools of Porto Moniz or Seixal will be chilly to comfortably enjoy in the colder months. They’re a really awesome way to spend a day in Madeira so the fact that I missed out makes me irked.
• Hikes: Again, this being related to the weather, everything will be wet. Walking in chilly and wet conditions is not a pleasant experience to me.

BUT, here are some pros:

• There will be very few tourists.
• Prices are usually better for hotels and flights.
• You will have a lot of places to yourself.

Sometimes off-season travel is the only time you have to take from work so you make it work. I wish I instead visited Madeira during shoulder season for example. Visiting in the months of May or September would give me the off-season vibes I love but not have limited me in the number of things I wanted to do. Knowing what I know now I would not have traveled to Madeira in December but I hope I gave you enough realistic expectations to make the decision for yourself.

Gladly, this itinerary is informative enough for any season so feel free to download it when you travel to Madeira. If you do, share a photo! Don’t forget to comment down below on whether you think Madeira is worth traveling off-season and what experiences you might have had there!

More off-season travel from Perfect Day Somewhere!

Simple Yet Awesome Off-Season Things To Do in Cape May

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Resort towns can be tricky off-season, you either end up in a ghost town or find yourself in a less crowded paradise. I heard many good things about visiting Cape May off-season and I’m here to tell you that those things are not wrong. My simple weekend getaway itinerary will give you enough to do during your little escape and let you relax a little too. I personally visited in mid-October and although a lot of places were winding down for the winter, it didn’t limit my plans too much.

In this guide, you will find some visiting logistics, along with a full two-day plan for your visit. 

Note that you may encounter some affiliate links in this post. They will not make anything more expensive for you but rather provide a small commission for me should you choose to book it via the link I provide. Since I do not charge for any of my awesome travel advice and don’t make you sign up for anything to download my stuff, I appreciate any link clicks and bookings through here 🙂

Quick Cape May Logistics

Transportation

Getting there couldn’t be any easier, just go all the way down the parkway 🙂 No seriously, when you get to Exit 0 you’ve arrived. If you’re coming from the north I actually found a bus route from NYC, first bus 319 to Atlantic City and then 522 to Cape May but with over 4 hours of travel time, I don’t know if that’s a smart choice worth the hassle. If you’re coming from the south you can take the Cape May ferry which goes between Cape May and Delaware. It transports cars too!

The main part of town isn’t that big so if you stay in the heart of Cape May, then everything will be within walking distance. There are a couple of attractions a short drive away too, so just like in most of New Jersey, you’ll need a car.  

In-season, you will find a free town shuttle called the Cape May Jitney. It runs between July and the end of September. If you have a special occasion, you can also rent these all to yourself! They run within a certain radius too which won’t restrict you to only staying in Cape May.

How long and where to stay in Cape May

Since there isn’t an overabundance of things to do in Cape May off-season, I would spend 2-3 days there. A weekend is sufficient enough to see the attractions and not feel too bored. I also recommend visiting during the weekend only as many of the attractions close on weekdays during the off-season. In season, however, you can easily spend a week there. 

In terms of where to stay, I would simply recommend staying as close to the main part of town as possible. This will allow you to walk everywhere during your weekend escape and not waste time looking for parking. The best thing about traveling off-season is getting amazing hotel rates that in the summer are 3-4x the amount. I was honestly surprised by how expensive hotels in Cape May are during peak months. A simple night at a decent place can start at $300+ for a night during the summer months. Note that a ton of B&Bs has a 2-3 night minimum too. That’s pretty pricey if you ask me.

While price is one thing to consider, another is availability. I booked my off-season trip almost two months out with very limited options. I don’t know if that’s the corona effect, but I strongly recommend booking ahead of time. My choices were limited to a $600 a night hotel and a small family-owned more budget yet still pricey, The Buckingham Motel. I can’t say that there was anything wrong with it, the owner was really nice and the property and rooms were very clean. However, the place is very outdated so if you like a more modern feel with good TVs and nice bathrooms, and updated kitchens (yes some rooms have kitchens), then this isn’t the place for you. 

When I mention good rates below, note that this is a pricey town. Good means under ~$300 a night 🙂 

Options: 

Rentals:

• Airbnb: If you’re booking far out in advance and traveling with friends, this is a great option for this area. It will save you money, and give everyone space and flexibility. 
• Cape May Rentals: Like a lot of shore towns, finding houses can be done through local rental agencies rather than Airbnb. The selection will be much larger but a lot of the places are rented out by the week.

Hotels: 

• Lokal is beautiful and extremely modern with two nights in-season priced at over 1k and off-season a little more than half of that. Its style and atmosphere are really nice.
• Congress Hall’s style is just the opposite of the above, screaming class and old money. The prices are similar too. It’s located right in the center of town too but also close to the beach. 
• Icona, Montreal Beach Resorts, and La Mer are a little under a mile walk to the town but located beachfront. Off-season rates aren’t bad and the proximity to the beach is awesome.
• The Grand Hotel is both, close to town and the beachfront. Off-season rates are pretty good for the area. 
• The Beach Shack is super cute and located close to the beach. It’s booked out months in advance and its off-season rates are great! 

Bed & Breakfast 

Cape May is extremely charming so staying in an old Victorian B&B is an experience within itself. 

• The Southern Mansion is pricey but it certainly doesn’t lack any charm.
• The Virginia Hotel is a classic in the area and it is an adults-only resort for those not wanting children around.
• Rhythm of the Sea has a 2-night minimum and it’s located right next to the beach. 
• Wilbraham Mansion is an old luxury house with a heated pool and jacuzzi suites. Has a great location too. 
• The Harrison’s style is awesome, contemporary old money? Is that a thing? Also a great location with pretty ok off-season rates. 

Budgeting in Cape May 

As mentioned above, traveling to Cape May is not a cheap weekend escape. Although traveling off-season will save you a good amount on your accommodations, it’s still a pricey town. Here is a very basic breakdown of prices. Expect to spend an average nightly rate of $200-$300 a night for off-season and $300+ in-season for accommodations. Restaurants are similar to city prices, $12ish a cocktail, $20+ for meals. Depending on the activity, that could cost you too. Expect to pay around $600 at the very very minimum for an off-season weekend getaway. 

Food options 

One of my favorite things to do in Cape May was to eat. Honestly, this place has some awesome food spots. Rather than making one list, I will give you my recommendations scattered in the guide below. 

Miscellaneous things to know about Cape May 

• If staying in town is not very important to you, you will find better rates in the neighboring towns. Although Wildwood wouldn’t be my first choice, hotels there are slightly cheaper. 
• Atlantic City is a little under an hour north of Cape May which could be a good stop on your way home. 
• When traveling off-season, always check if a place is closed for the season. Although the town stays open for the most part, some places do indeed close. 

Perfect Cape May Weekend Itinerary 

Day 0

Evening Arrival: Drinks and Dinner

I personally like to arrive Friday evenings and stay until Sunday night compared to arriving Saturday mornings and leaving Monday mornings. That is the plan I will lead with and try to convince you that it’s the best way to travel. 

After checking into the hotel and freshening up, head out to town and don’t waste any more time. Arriving later in the day does limit you in terms of which places you can go out to eat since Cape May is somewhat of an “early town.” Here are a couple of good options for your first night dinner and drinks: 

• Harry’s Ocean Bar and Grill: If you’re near the beach, this is a solid pick for dinner and drinks. It’s pretty casual, the food is great and it’s open till 10 pm or so. When traveling off-season, the rooftop part might be closed later in the day and weekend hours end an hour earlier during certain months. 
• Fins: Located right in heart of town, this awesome place has a cool vibe with an aquarium inside. It’s casual yet shore trendy. Hours vary by the day but dinner is served until 10 pm. 
• The Boiler Room is an underground pizza bar that is only open on the weekends. It’s open late and has an awesome ambiance. This should be on your best things to do in Cape May list! It’s located in the basement of Congress Hall. Follow the signs to the bathroom and it will be located right next to it. 

Day 1 

Normally in most of my guides, I say wake up early and start your day to see the most of each place. This time I’ll tell you that if you’re traveling off-season, don’t feel guilty about sleeping in till 10 am or so. At the end of the day, with the limited about of things you can do in Cape May off-season, it’s important to schedule some beauty sleep in too 🙂 

We brunch in Cape May 

Brunch is the most important meal of any traveling day. When doing my research, every single blog mentioned MadBatter as the place to eat the “best lunch you ever had.” Whenever I see this amount of recommendations for a place, I get suspicious. Listen maybe it is that good, but it usually ends up being crowded, overpriced, and rushed due to its popularity. You can’t make a reservation there either. Arriving around noon on a Saturday and off-season, the line was still enormous and the wait was under 2 hours. I couldn’t do it. 

I ended up opting out for another popular pick The Blue Pig Tavern located at Congress Hall. Although you can make a reservation (which I highly recommend), I walked in and was seated in under 10 minutes. They have an awesome inside room and a pretty garden seating area too and either way they’re both nice. Let me tell you, this place DID NOT disappoint. The food was delicious probably for the reason that their ingredients come from the local Beach Plum Farm. Another popular area pick, their food was delicious and I highly recommend it. 

Some other brunch spots for your consideration: 

• Elaine’s is a hotel, boutique, and restaurant. They have a nice outdoor space and good ratings for lunch. 
• Uncle Bill’s Pancake House is one of those shore chains everyone raves about. Passing by around lunch, you’ll also see a big line of hungry pancake lovers. 
• George’s Place is a fancy Greek diner that’s a BYOB and cash only. Make a reservation and enjoy this unique spot. 

Shopping time! 

Explore Washington Street Mall  

Washington Street Mall is a charming area in the heart of Cape May that has tons of shops, cafes, and restaurants. It can get crowded during the day but it’s still a really cute place that has that downtown feel. It’s not that big but don’t forget to explore the side streets which have some hidden gems too.

In terms of shopping, you won’t find chains here but rather a collection of all locally owned shops. You can buy a variety of items ranging from souvenirs, trinkets, jewelry, and clothes to snacks. If you’re more of a people watcher, grab some sweets at Crepe May or Uncle Charley’s Ice Cream or coffee at Coffee Tyme and enjoy the area. If you prefer an afternoon drink while people watch check out The Ugly Mug or Delaney’s Irish Pub. Depending on how much you browse, you can easily spend an hour or two in this area. Here is a website with a list of all the available shops. 

More Shopping at West End Garage 

After spending some time at the Washington Street Mall, you’ll notice that despite the large selection of products, you don’t see many artisanal or handmade items there. This is why you’ll head to West End Garge which is a large shopping space located about a 10-minute walk from downtown. This whole place is filled with a large selection of local artists’ crafts. It even has a small bakery and cafe on site. As you browse throughout the whole space you’ll notice that each of the small shops doesn’t have cashiers in them. You will actually pay for anything you find there in the first room you enter so don’t get confused 🙂

See Cape May’s Beach & Lighthouse 

If you’re traveling here off-season, you’ll, unfortunately, miss one of the best things to do in Cape May which is the beach. However, just because you can’t swim, doesn’t mean you shouldn’t see its beauty.

Here are a couple of stops for your afternoon in Cape May. Note that the easiest way to see all these spots is to drive between them. They’re about 10 minutes from each other and are all easily seen in one afternoon. 

• A cool spot to watch some talented surfers (even off-season) is near Sunset Pavillion. There is a ton of them and they’re insanely talented.
• Cape May Lighthouse is a local landmark that’s one of those “top things to do in Cape May” things. You’ll need to purchase a $12 ticket online and entry is until 5 pm. 
• Sunset Beach is located right by the lighthouse and as its name suggests is the place to see the sunset. 
• If you like the sights of boats against a sunset sky, visit Schellenger’s Landing which houses a couple of south jersey marinas and waterfront restaurants. 

Dinner Time 

There are many cool places in town to grab dinner. For my pick, I went to a decently rated Italian place in town. I’m obsessed with good pasta so I was looking forward to this. Ugh, as much as I loved talking to the owners and the ambiance of the restaurant, the food was not great at all so I won’t recommend it. So instead, here are other picks that were recommended to me: 

• 410 Bank Street: A New Orleans-inspired stylish restaurant with award-winning dishes. 
• Sapore Italiano: An Italian gem in town that won’t disappoint. 
• Elaine’s which is mentioned earlier in the post for brunch has some cool outdoor dining vibes at night. 
• Lucky Bones is a very popular casual pick in town located a short drive away. 

For more picks check out this list of restaurants open year-round! 

Bonus – Night Cap time!

If you’re not ready for your day to be over, head out for a drink. These restaurants are open a little later for a nice after-hours cocktail: Ugly Mug, ​​Delaney’s Irish Bar & Restaurant, and Fin’s Bar & Grill.

Day 2

Morning 

Get ready for another day of Cape May Attractions. For the start of your day, I recommend grabbing a coffee and something sweet at Madison Bakery on Beach Avenue. I’d pick that location as the in-town one does not have the greatest reviews. At the beach one, however, I had one of the best chocolate croissants around.  

The next activity for a nice Sunday morning is renting a bike and exploring the town a little more. Shield’s is a bike rental place right next to the bakery and they offer pretty decent rates for the area. I recommend biking the promenade on which you can bike off-season after 10 am.  

Afternoon 

For lunch head over to Exit 0 Filling Station, a really cool restaurant that’s a gas station. Since I visited in the early off-season, I was able to get a table outside. If it’s too cold, however, the inside is just as awesome and I suggest this place for a unique dining experience! The menu is unique too, it’s a combination of burgers and curries. Weird yet tasty. 

Wineries

One of the more awesome things to do in Cape May in the fall is to visit one of the beautiful wineries. I was really excited to see Willow Creek Winery in the West Cape due to its great reputation and stunning grounds. I didn’t check their website though and when I arrived they closed for a private event. So always check 🙂 I did get to see the grounds a little and they really were stunning. On Fridays and Saturdays, they set up firepits in the evening too! 

Another popular winery in the area is Cape May Winery. That’s where I ended up since the above was closed. I do have to say that their way of seating is a little rare, you have to wait to be hostess seated but then you also have to order your food at one window and your wine at another. Can’t say that I loved that setup but the wine was worth the hassle. Prices started in the upper $20s. They have live music on the weekends and a cute little shop on site too. 

If wine isn’t your thing, Cape May Brewery offers a nice selection of beers and seltzers. They have a tasting room and beer garden on a first come first serve basis. They’re also open all year round so you don’t need to worry about being there off-season. 

Sunday Evening

Rather than heading home, enjoy the last hours of your weekend getaway and stay in town just a little longer. Ignore the Sunday scaries with Mad Batter’s open mic night on Sunday evenings or take a nice stroll on Washington Street when it’s all nice and quiet.

If you’re driving north, another option that’s a little more involved and extra is making a short stop in Atlantic City. It’s about an hour north of Cape May and if you head out in the afternoon, you can squeeze in a couple of hours there too. Casinos don’t close so if you have time, it’s a cool stop to enjoy the gambling paradise of New Jersey. 

Map

Bonus Tips for your Cape May Adventure

Winter-Specific Events for Things to do in Cape May 

Christmas time is magical even down the shore. Cape May becomes alive closer to the holidays and for a good reason. People flock to Washington Street Mall for Christmas shopping while enjoying the decorations in the mall. The Victorian houses also get decorated nicely for this season. Here are some Cape May winter events for you: 

• Cape May Christmas Parade: This year it will be on December 4, 2021. The owner of the motel I stayed at highly recommended it for a cute winter activity.
• The tree lighting ceremony at Physick Estate is on November 20th. 
• Congress Hall hosts a Winter Wonderland on its grounds starting December 1. 

More Activities 

If there is something on my list that you didn’t like, feel free to swap it with the additional off-season Cape May things to do below: 

• Emlen Physick Estate: If you’re a history nerd, you can visit this old mansion museum for a tour. Closer to Christmas, they decorate the estate to authentically represent a Victorian Christmas. Tickets are $20 for an adult.
• Whale and dolphin-watching cruises are very popular down in Cape May. Off-season rates might be a bit better but the air much cooler 🙂 Here are a couple of companies that run these tours. 
• If theater is on your travel must-do list, check out East Lynne Theater Co which hosts a variety of shows even in the off-season. 

​​Final Thoughts 

I hope that the itinerary above gave you a nice plan for some awesome Cape May activities. Although traveling off-season does have its cons, it’s also a unique experience allowing you to see this place without the people and annoyances that come with the in-season crowds. Yes, maybe you will miss the beautiful beaches in the summer, but who says you can’t come back in the summer as well 🙂 

Cape May is a gorgeous historic Jersey shore destination. I hope you add this place to your local bucket list and enjoy it as much as I did. Finally, as always, if you have any suggestions any other useful info that you think should be added to my off-season Cape May list, leave them down in the comments! 

More Off-Season Guides

I love local off-season weekend travels! Make sure to check out my Newport and Montauk guides for honest opinions on whether off-season travels there are worth it!

And below are some additional local guides too!

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I should preface that these expectations are for an average, non-clout-seeking traveler with a non-Hamptons salary. If you have a summer home or a large wallet, you probably won’t benefit from this guide. With that said, let’s get to the brutally honest Montauk travel guide for all the fellow “broke b*tches”. I’ll cover the logistics of getting there, things to do, and tell you what traveling there entails.

Note that you may encounter some affiliate links in this post. They will not make anything more expensive for you but rather provide a small commission for me should you choose to book it via the link I provide. Since I do not charge for any of my awesome travel advice and don’t make you sign up for anything to download my stuff, I appreciate any link clicks and bookings through here 🙂

Montauk Travel Guide – Most Important Things to Know

Where is Montauk

The Hamptons collectively refer to a group of towns in the Eastern part of Long Island. Montauk is at the tippy tip and it’s considered the more “low-key” of them all. What once was a quiet resort/fisherman town is now the chosen destination of many influencers that want to be seen. I wanted to see this place for myself as I’ve heard very mixed opinions about it. So I planned my 2-day route with stops along the way that would let me admire the other Hamptons even for a little and see what the hype is all about.

This itinerary is for a simple 2-day local weekend getaway. I’ll give you my best tips and first impressions that I experienced there. Before we jump into the plan though, here are some quick logistics about this destination.

Montauk Transport

Getting to Montauk is easy. The first option is to hop on the highway from NJ/NYC and in 2.5-3 hours you’ll drive through all the Hampton towns into Montauk. Note that this will not be the case in the summer when you should add an additional hour or two to your drive due to traffic. The second option is a bus from the city like the Hampton Jitney or Hampton Luxury Liner. That ranges anywhere from $30-$70 each way which is not horrible. However, it does limit you to how you’ll get around town when staying there. Lastly, you can take the good old LIRR with a ton of stops along the way for a similar rate. The main advantage of a train ride, however, is skipping that dreadful traffic.

I opted for the driving option and there was virtually no traffic getting there. However, this was done in April, off-season for that area. It took about 3 hours to reach Montauk but we also made small detours along the way.

When you arrive, getting around is easy as most of the town is more than walkable. If you want to venture out to the lighthouse, wineries, or beach though, without a car this will not be the easiest of tasks. I personally and naively estimated the town to be a bit bigger than what it ended up being so I was a tad shocked when my drive within town ended within a couple of minutes.

Hotels in Montauk

First things first, BOOK SUPER SUPER SUPER EARLY.

Montauk is a smart town, you know why? Because keeping hotel prices at $600+ a night during the season keeps the broke b*itches away. They’re doing a great job because I certainly won’t be paying that to get back there. Every travel guide you read will tell you that Gurney’s or Surf Lodge is the absolute place to be. Are they nice? Heck yes, but will I drop $1000+ for a weekend at an Instagram hotel? Probably not. Some cheaper options include Montauk Blue Hotel or Royal Atlantic.

I stayed at Sea Crest Resort in Amagansett about a 10-minute drive outside of Montauk. My room had a 1 bedroom apartment and a sea-view balcony. At $300 a weekend night, it was a great place to stay in the area (compared to the insane rates 10 minutes away). Weekdays in April/May are even sold at half that price so if you’ve been dying to see Montauk for yourself, that’s your smartest option. For a deeper dive into cool spots check out Broke Backpackers Hotel recommendations there too.

All I’m saying is that you should simply know what to expect and not be shocked when you start looking at property prices.

Useful Things to Know for Montauk Travel

• Most people are dressed to impress so pack your best outfits. Chances are that you’ll see many Birkins around. Old money, new money, and just money all around.
• Restaurants are pricey and you’ll need a reservation almost everywhere.
• Gas is insanely expensive in town. There will be at least a $2 difference compared to the average prices so fill up before getting there.
• There aren’t that many things to do in Montauk aside from dining, shopping, and lounging. Unless you’re a part of that community, this destination may not be as exciting as you might think.

Your 2-Day Montauk Itinerary

Day 1: Drive through the Hamptons & explore the town

Stop 1: Hampton Bays

If you’re driving in, your first stop will be a cute restaurant called Rumba Inspired Island Cuisine & Rum Bar in the Hampton Bays. The place is cool, with fancy tiki feels on the inside, an outdoor patio, and a vintage bus outside. It had a ton of cocktail options and the food was pretty tasty. The place got packed by 11:30 am so I certainly recommend making a reservation.

The crowd was mixed. Some families celebrating birthdays with their kids, some Instagrammers, and some other fancy humans. This place was probably my favorite spot out this weekend so I genuinely recommend grabbing a meal/drink there. Aside from the restaurant, there isn’t much to do in the Hampton Bays from a touristy perspective.

Stop 2: Southampton

The next stop isn’t so much of a stop because you can admire the beauty of Southampton from the car 🙂 Driving in the Cooper Beach direction you can spot the mansions on Meadow and Gin Lane. Although the hedges will block most of your views, it won’t be hard to see why this is the most sought-after place to be. Driving through the side streets, I appreciated the location’s beauty. Streets lined with tall trees on both sides give the place a very special vibe. If you’d like to explore more of the town, you’ll find the boutiques and restaurants clustered near Main and Jobs Street.

Stop 3: Hotel check-in

If you drove early in the morning, you might get to the hotel before check-in. I always recommend asking if your room is ready though because 7/10 times it is. I stayed at Sea Crest Resort and they let us check in early so around 2:30 pm. This particular hotel was actually nice, located in Amagansett right on the beach. The downside of an April visit is that it’s way too cold to lounge outside. While Jersey had a beautiful warm and sunny day, the cold winds of the island made the beach experience not as pleasant. However, it was nice to grab a cold beer, enjoy the peaceful views and inhale some fresh air.

To be honest I did not expect the temperature difference to be so drastic. The trees weren’t even blooming yet compared to Jersey’s super high pollen counts. I took a fall jacket with me and ended up wearing it the entire time. Make sure to check the temperature before visiting and don’t assume that it’s as warm as its 2-hour neighbor.

Stop 4: Montauk

I was so excited to check out what the hype was actually about. But this is where I have to be a major party pooper and say whomp whomp, “downtown” Montauk is not that great. There is a circle and all of its 3 streets with some shops and restaurants.

The first stop was a quick recharge at Hampton Coffee Company and Montauk Bake Shop. I wanted to stop by Left Hand Coffee for its cool vibes but it was closed. We walked around a couple of overpriced stores in that area and quickly realized that a $100+ crop top is the norm there. Being a beer fanatic, I really wanted to check out Montauk Brewing Company, but due to the long wait, I ended up getting a growler to go instead.

Here are some other places to grab a drink that most people rave about:

• The Surf Lodge: hotel and restaurant known among the Instagrammers/TikTokers. Criticized for horrible service.
• The Montauket: is known as the best sunset spot in town.
• Navy Beach: another trendy popular place with an outdoor drinking scene.
• Liar’s Saloon: located on a dock, this is your local “dive” bar.
• The Point Bar and Grill: local sports bar in the area.

Stop 5: Montauk Lighthouse & Local Nature

The drive to the lighthouse is another 10-15 minutes east of the town. It was closed for renovations when I visited but the whole area was pretty nice. It was crazy windy so I didn’t get to explore much but I imagine that in the summer it’s a nice place for a stroll.

On that route 27 drive, you can find Deep Hollow Ranch, which allows you to go horseback riding in season right on the beach. Another landmark in that area is Camp Hero State Park, a nice park to get some outdoor exercise. If you love conspiracy theories, check out this article about the dark secrets of this exact park. Another nature stop is Shadmoor State Park.

If you’re craving some exercise and outdoor activities, there are many shops in Montauk offering bike rentals. From what I saw the trails there look great. Your Montauk travel wouldn’t be complete without at least getting some of its outdoor beauty in.

Stop 6: Dinner time

After exploring Montauk, we needed some rest and headed back to the hotel. Also, a cocktail before dinner never hurt anyone 🙂 Even off-season, it was hard to get a reservation a week and a half ahead of our visit so if you’re planning to visit the town, make sure to get those in ASAP. The only thing we were able to get was a “last-minute” table at Muse at the End. The food was good but the selection wasn’t the greatest and it was hugely overpriced for what it was. The crowd was a little fancier too. Overall the experience was fine but I wouldn’t say I fell in love with this place.

Here are some other highly recommended places for dinner in town:

• Harvest on Fort Pond – a family-style town nook
• Sammys – a low-key local staple
• The Shack – a nice place right in the heart of town
• Inlet Seafood – located a little further away but known for its amazing Seafood
• Salivar’s Clam and Chowder House – seafood place located at the dock with a cool outdoor terrace
• Gosman’s – another place on the dock with a topside terrace perfect for sunsets
• Scarpetta Beach – a boujee spot at Gurney’s

Bonus stop: Nightlife in Montauk

Montauk is the place to party in the summer. At least that’s what I hear. I’m a grandma so after dinner I snuggled up in my blanket with a glass of wine and called it a day. So if all day of exploring didn’t kick your butt yet, make sure to make your way out at night. The drinking places I mentioned above usually have something going on at night.

Day 2

Stop 1: Breakfast

Since I am an espresso and a croissant kinda breakfast gal, I was happy with my chocolatey find at Hampton Coffee Company. If you’re looking for something more filling, try Joni’s a known local spot with amazing breakfast options, or Anthony’s Pancake House, a low-key spot with good prices.

Stop 2: Winery

Since this is a two-day itinerary, I recommend stopping by a winery on your drive home. Long Island is known for its wineries and a lot of people love taking their private buses there for special occasions. There are a ton of places in the Hamptons to get some quality wine so if one more person recommends Wolffer Estate and their rosè, I might quite vomit on myself. Don’t get me wrong, their rose is good but the spot became more famous for getting the Instagram picture with a location tag than the actual wine.

Here are some additional picks for you to choose from. Don’t forget to make a reservation if you’d like a tasting.

• Channing Daughters– Bridgehampton. A charming winery with a unique sculpture garden. Tastings are $25 a person and they also have small snacks available for purchase. Wine prices are typically ranging from $18 to its most expensive bottle at $60.
• Jamesport – Jamesport. Beautiful outdoor space with a kitchen on-site that serves delicious pizzas. They do have tastings by reservation and most of their bottles run between $20-$35.
• Clovis Point – Jamesport. This is a by-reservation-only spot with very specific reservation and on-site rules. Their prices are a little steeper but they have a nice outdoor space and high reviews!

North Fork wineries may be a little further out however if you have some extra time during your Montauk travel and want to see that part of Long Island, this is a good excuse to venture out in this direction.

• Duck Walk – Southold. The North Fork wineries are stealing Hampton’s spotlight. Duck Walk offers $12 tastings with reservations and allows you to purchase some snacks in addition to allowing you to bring your own picnic. A ton of their wines are under $20 too. Some of their reviews however are concerning many commenting on the disrespectful staff. Remember, sometimes you get what you pay for 🙂
• Kontokosta – Greenport. Located even further into the North Fork, this modern winery currently offers bottle sales only and no tastings due to COVID. They’re by reservation only and do not allow outside food. It’s located on the water allowing for some unique views however familiarise yourself with all their current policies before visiting.

Other miscellaneous stops along the way:

Before ending your Montauk getaway, make sure to grab a fresh lobster roll at The Clam Bar in Amagansett. I will vouch for 100% for its quality and it was totally worth the $30.

Carissa’s Bakery is highly rated in East Hampton and located centrally if you’d want to peek into this Hampton’s lifestyle.

If you’re planning to stop somewhere else on your drive home, Tutto Il Giorno in Southampton and Sag Harbor won’t disappoint. The food is delicious and the space is very bohemian chic but expects steep prices.

Summer Time Beach Time

Since I visited Montauk off-season, going to the beach was not an option. However, in its peak season, this is one of the major reasons to visit this area. Since I am not one to give you beach advice as I only spent some time on one in Amagansett, I would check out this simple beach guide by On Montauk, to give you a better idea of what to expect from each. Here is a beach list and descriptions from their website:

• Amsterdam Beach: hike to access, remote but worth the hike.
• Ditch Pains Beach: surfer, popular, and with permit parking.
• Edison Beach: central popular beach with limited public parking.
• Gin Beach: quiet family beach with permit parking.
• Hither Hills: family beach with public parking.
• Kirk Park Beach: recommend the beach if you’re only in town for a day. Public parking.
• Montauk Point State Park Beach: not really a lounging beach, rocky for hiking. Public parking.
• Navy Road Beach: pebbly quiet beach, lots of boats.

Final Thoughts on Montauk Travel

Would I visit Montauk again? Probably not. Ugh, I hate to dislike places but let me explain why Montauk is not as dreamy as you might imagine it is.

First, this is not a place for a 5 or even 6-figure income person. Even the off-season rates are nuts and paying $1000+ for a weekend in peak season for a hotel is just silly. To put things in perspective, I spent two weeks backpacking in Peru for a little over that. Yes I know I’m comparing a South American country with a famous resort town in NY but if you’re an explorer like me, you get the point. I call myself a champagne backpacker because as much as I love nice things and spending money on experiences, a trip to Montauk is contributing nothing to my travel life.

Second, there really isn’t that much to do in this town. When I tell you that you can see everything there is to see in less than a day, I mean it. Aside from restaurants, a couple of nature preserves, and boutique shops, there is nothing special to do there.

Third, this is a spot to be seen and take pictures to say you spent a day in the Hamptons. As much as I like my pictures and posting about my travels, I do things for the sake of the experiences first. If I don’t like a place, I will be honest about it and not feed you bs that it’s a wonderful place to be.

But change my mind.

I’m certain my perspective on Montauk travel would be 1000 times different if I stayed in a large house with a nice pool or got that $1000 a night resort room without even thinking about the price. This post is aimed at an average Kasia who is looking to explore what her backyard has to offer.

So with huge disappointment, I vote Montauk a pass.

But Kasia, you traveled there off-season. What do you know? Well to compare, I had a phenomenal off-season experience in Newport, Rhode Island so if you’re curious about what made it different, find it in my post about it.

So should you visit Montauk?

Depends on what you’re looking for. I gave you all the tools and opinions to make that decision for yourself. Here is the research I gathered to make it easier to decide whether Montauk travel is for you.

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Is Newport worth your time in the winter? For sure. Lucky for you, I tested it out and I’m happy to share my tips and the perfect Newport weekend itinerary with you.

My two-day Newport itinerary is not for the traveler that likes to sit and relax at the hotel for hours on end. It’s designed for an explorer like me. Someone who wants to see a decent chunk of the city in the short amount of time there visiting yet still pausing at each spot to enjoy it.

Note that you may encounter some affiliate links in this post. They will not make anything more expensive for you but rather provide a small commission for me should you choose to book it via the link I provide. Since I do not charge for any of my awesome travel advice and don’t make you sign up for anything to download my stuff, I appreciate any link clicks and bookings through here 🙂

Quick Newport Logistics

Getting around Newport

The city of Newport is located on Narragansett Bay in Rhode Island. The 3.5-hour drive from New York goes by in no time. Once you cross the Pell Bridge, you’ll enter the “touristy” zone of Thames Street. If you’re staying in that nook of Newport, you’ll be able to get around on foot. Note that the Newport Mansions and the Cliff Walk are located in the other, more eastern part of the city. To get there you’ll need an uber or the city bus. Your two public transport options are Bus 67 which will take you to all the mansions side or Bus 63 which connects you to the northern part of the city. Between Memorial and Columbus day you can also take the harbor shuttle for some awesome port views.

How long and where to stay in Newport

It’s not surprising that Newport is an expensive city. It’s one of the oldest resort towns in the US and used to be a small playground of the rich of the rich. One of the perks of traveling there off-season is the good chunk of money you can save on your accommodations. In the summer, decent centrally located hotels can easily range from $300 and up a night but off-season you can stay for half of that.

A couple of more-known places in town are gorgeous but will cost ya a good amount. No matter what you end up choosing based on the size of your wallet, I recommend it being close to Bowen’s Wharf. While it’s the most touristy area, you will like it for being the livest part of town. Remember that winter is not busy to begin with so staying far away from the center to save a few bucks might not be the way to go. With a short amount of time in the city, the last thing you’ll want is to be far away from the action. I stayed at the Cleaveland House Inn, a small family-owned bed and breakfast. It was a budget option near Thames Street but I loved the ambiance and how helpful the staff was! The parking lot was super convenient too as it allowed me to park 3 minutes away from the main part of town.

As far as the length of your stay, a long weekend is sufficient to see the highlights of this town. I arrived around noon on Saturday and left on Monday after checkout. It was a good amount of time allowing me to catch all the major spots and still relax a little. In the summer, 3 days would be recommended not to rush the experience and account for the delays caused by more people.

Budgeting in Newport

Things add up quicker than you think in Newport. It’s easy to spend a decent amount of money even in a short amount of time as a weekend. Here are some examples of what you should expect to spend there. A hotel will cost you around $150 a night, that being on the cheaper side. For meals, breakfast can be $20-30, a good lunch with drinks about $60-100 and if you want to splurge on dinner, that’s another $100+ per night. The mansions entry is also $26, and I imagine you wouldn’t want to skip that. That’s just the basics of what you can expect to pay and that’s pretty pricey my friend. And unless you’re carefully planning the more budget spots, you will get stuck paying the prices I just listed. So no, Newport is not a cheap destination.

What to wear in Newport during the winter

I think it’s safe to say that everyone’s hesitation about traveling to Newport Rhode Island in the winter is the weather. When I visited, the temperatures were around 25 to 40 degrees during the day. That’s pretty chilly for a town on the water but I was quite surprised that it wasn’t brutal compared to how that same temperature feels in New York or even Boston. When packing, I would consider warm and comfortable shoes first. You will regret having your feet cold because you decided to wear cute winter boots. For the amount of exploring, make sure to prioritize comfort and warmth over everything else. You’ll also need a heavy winter jacket, hat, and gloves. Don’t forget the standard warm sweaters and thick pants for underneath. I know this sounds like common sense but you’d be surprised how many tourists walk around shivering because they wanted to look good rather than be warm.

Newport Rhode Island Travel Guide

I spent two days in Newport this February and I am here to show you that you can have an amazing time there even in the winter. My plan included seeing the highlights without trying to squeeze too many things in. There is a ton more you can do in-season too but if this is your first time in Newport, my plan should be a good start for you. This is your two-day travel guide for Newport Rhode Island.

Day 1

Your best bet is to start the day as early as you can. It took me under four hours to reach the city from New Jersey with only one rest stop along the way. Since I traveled off-season, my accommodation was able to check me in super early right before noon. We left the car in the parking lot on-site, freshened up, and headed straight out. Our carefully planned route ended up being just enough not to exhaust ourselves and feel accomplished at the end. This is what I will share with you for your plan and I hope that you can embellish this travel guide with your own stops as well 🙂

First Stop: Lunch time at Diego’s on Bowen’s Wharf

After hours of driving, the first thing I wanted is some tasty food and a cold beer. The perfect first stop on the trip was Diego’s, a Mexican spot with some cool vibes. A reservation on the weekend is a must because of the limited indoor capacity. There are three main dining areas, the outdoor heated patio, the lower indoor space, and an upstairs dining room with stunning views of the port. I made the reservation for the upper level and it was the perfect first experience of this city. The food was super tasty and the drinks were even better. A couple of shots of tequila got me ready to explore the town.

Next: Recharging and exploring the shops of Bowen’s Wharf

After an amazing lunch at Diego’s, I recommend spending some time in the Wharf. It’s such a cute area to explore for local shops and a nice lively vibe of the town. However, to stop yourself from losing stamina, you’ll need some caffeine. Newport has awesome coffee. Seriously, for probably having 6 cups there over the whole weekend, I did not have one bad one. On the Wharf, we ended up at the Coffee Grinder which has a cute outside area to sit on the water. The coffee was great but the prices were just nuts for two cups (close to $20 for black coffee). I made sure to enjoy some time on the little patio just to make it worthwhile.

Bowen’s Wharf has a ton of shops so explore it for as long as your heart desires. Make sure to walk near the boats and admire their winter beauty. This is also the spot from which a lot of boat tours leave. I did not see any running in the winter but as early spring approaches, that might change soon. If you travel in the future during the winter months, make sure to check if the Newport winter festival is back on.

Then an afternoon walk down Thames Street

Thames Street is a cute touristy street. The part you care about runs between Marlborough Street down to Wellington Ave. If you’re starting from Bowen’s Wharf, walk south (making a right out of Bowen’s) and explore the little local shops in Newport Rhode Island. I recommend making a loop there. There are so many boutiques and trinket shops. My favorite little shop was the Salty Babe for some new fashion trends. If you walk fairly far down, you should grab a drink at O’Brein’s a very known pub in the city.

Once you make your way back, stop at Kilwin’s for some out-of-this-world chocolates and ice cream. Another cool spot I recommend in that area is Brick Alley Pub. It’s super known but the decor and service make it worth stopping at for at least one drink. If you still have some energy left, there is another small shopping area at the Long Wharf Mall. It’s mostly retail chains and only a couple of local shops.

Oh and then don’t forget to relax a little

Now after half a day of exploring, you will need to rest a little before dinner. Make sure to take some time at your hotel to relax and enjoy some time for yourself. I’m always guilty of rushing and packing my schedule with things to do and forgetting to relax while on vacation. In Newport, I almost made the mistake of pushing through the schedule, but I stopped myself to pause even for a little. After driving almost 4 hours and then spending another 4 exploring the town, I didn’t realize how bad I needed a serious nap. I think you will do the same.

To end the day, have dinner at Mamma Luisa’s

There are SO many good dinner options in town that it’s hard to choose one. My go-to at almost any destination is always the best pasta in town. I found Mamma Luisa’s online and it certainly did not disappoint. The restaurant is located down on Thames Street, a little further away from the main touristy part. It’s inside an old house and serves delicious meals. Parking could be hard so Uber may be a good choice.

Just kidding, time for a night-cap

If you’re a drinker like me, finding a bar that’s open late could be a struggle. The Fastnet Pub was one of the only open spots near my accommodation for some late-night brews. Can’t say that it was a classy experience but hey, you need to see all the parts of town right?

Day 2

The first day was packed for us so sleeping a little later than expected was almost unavoidable. Especially after the nightcap stop. I wanted to stick to my travel plan and after a strong cup of coffee, I was ready for day two of exploring Newport Rhode Island in the winter.

Are you ready for another full day of Newport activities? Because on the second day, you will get more of the Newport vibes outside the area of Thames Street. You’ll spend time outside for a good chunk of it so don’t forget to bundle up in your warm clothes.

Start your day with a filling breakfast

Before heading out for some more exploring, make sure to grab a good breakfast. I enjoyed the coffee and food at Drift Cafe right on Thames and also at the Cru Cafe located inside the town so that’s what I recommend to you. Other known spots that were recommended to me are The Corner Cafe, The Franklin Spa and The Hungry Monkey.

Then, grab a beer at Newport Vineyards

After breakfast, take a trip to a different spot 15 minutes outside the town, the Newport Vineyards. It’s a winery/brewery/restaurant. I did the beer tasting there instead of wine and it was good but crazy pricey for the amount you get. The food was ok too but nothing spectacular. The space is very large but I would make reservations a couple of weeks in advance as it’s a very popular spot. The grounds are pretty but in the winter there is not much you can do there aside from drinking at the moment. Although the place did not blow me away, I recommend grabbing a beer or a glass of wine and some small tapas. It’s still super awesome and is located a little out of the way, lets you see another side of this area.

Don’t forget to tour at least one Mansion

You can’t visit Newport and not see at least one of the famous mansions. Check out how to richest families in the states used to enjoy their summers at these grand estates. They’re known as the Gilded Age Mansions and they were built in the late 1800s. Their extravagant European decor makes them a super unique activity on the East Coast. Even if you’re not into history, I recommend visiting at least one of them on your Newport trip.

Unfortunately during my visit, only The Breakers was open. It was once the estate of the wealthy Vanderbilt family and is probably the most known mansion in the area. The current price as of February 2021 is $26 and the last entry is at 4 pm. Parking is super convenient on-site too and it’s free. There are no operating tours but through the NewportMansions app, you can listen to the audio tour as your walk around. Don’t forget to bring your headphones with you if you’re planning to do this. It’s scheduled to close between March 1st and May 27th again.

For the other mansions, The Marble House is scheduled to reopen on March 1st this year and the Green Animals Topiary Garden in early April. It doesn’t look like The Elms will open until the fall and The Rosecliff is not on the schedule this year. Check out the Newport Preservation Society for the most up-to-date opening information. If you’re curious about the history of the mansions, check out the full list of them here.

And of course, walk The Cliff Walk

Newport’s tourism is known for the mansions but also for the Cliff Walk. It’s a promenade along the eastern shore that is about 3.5 miles long. If you have the time doing the full round trip allows you to see multiple perspectives while also getting some exercise in. The main parking is around Memorial Boulevard at Easton’s Beach and also there are meters near the 40 steps point. If you’re planning to do a longer walk, I suggest parking in that area. However, if you’re visiting the Breakers, you can just park there and walk a street over to access the Cliff Walk from Ruggles Ave. Turning right towards the southern part has a little rough rocky terrain. That continues to Belmont Beach with a few more challenging parts of the trail being located at the end. The left, more northern part of Ruggles is lighter and has some amazing mansion views. The northern part is more crowded but also easier on the terrain.

Finish the trip with a beautiful sunset and a boujee dinner

First, don’t forget to rest a little after the mansions and the Cliff Walk. Then, if the weather is clear, make sure to head to the wharf to catch the sunset. There is nothing prettier than sailboats, calm waters, and that pastel sky with a bright orange or red sun coming down in front of your eyes.

For dinner, I recommend 22 Bowens, a fancy steakhouse with the perfect ambiance. It is a little pricey for an average traveler but worth setting some funds aside for. Other places that won’t disappoint but won’t break the bank are The Red Parrot, Midtown Oyster Bar, or Sardella’s.

Final Thoughts on a Newport Rhode Island winter

Newport Rhode Island in the winter or even early spring is an amazing idea for the following reasons:

1) There are no crazy crowds, allowing you to peacefully eat out, see mansions, and do the Cliff Walk.
2) It’s half the price of your accommodations.
3) Parking is available (almost) everywhere.
4) There is almost no traffic.
5) It feels like you have this whole city to yourself.

And while I will be returning in the summer, my winter memories of Newport will always be very special.

I hope you found this guide useful and that I showed you that winter should not be stopping you from visiting this destination.

If you have any recommendations or thoughts that you think are useful for this travel destination, I would love for you to share them in the comments!

Map of Newport Rhode Island

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Was Key West all that I imagined it would be? Yes. There were many older couples having the time of their lives there. However, there was also everyone else having an amazing time too. I honestly cannot wait to go back and spend more time in Key West. It feels like a tropical destination without leaving the country.

In this itinerary, you will find some travel logistics, and cool things to see, and be able to download a weekend in Key West itinerary for your travels. If you’re going to South Florida, don’t forget to check out my Miami Guide and a Miami Girls Weekend getaway!

Logistics of Visiting Key West

Where and how long to stay in Key West

Key West can be expensive for accommodation, so it may be more cost-effective to stay in a location closer to the action on Duval Street. If you are traveling with a group, you could consider renting an Airbnb or VRBO, but these options may not offer significant cost savings. There is a hostel in Key West, but at $90 per bed in a dorm room, it may be more economical to stay in a hotel.

I personally stayed at the Douglas House, an awesome pick in town. There was parking onsite, the staff was super helpful and friendly giving us recommendations outside of the typical tourist trail and the rooms were huge! A cute little pool along with a stunning garden were also great additions to the property.

As far as length, you can see everything in a day or two but chances are you’re not going to Key West looking for cultural adventures. It’s a place to relax, have a drink, and lay on the beach. So spend a weekend there and you should be ok, especially with the high prices in town. Although pricey, it’s not ideal to see Key West in one day.

How to get to Key West

Key West is the Southernmost point of the US which makes it a unique destination. Its tropical vibes will make you feel like you’ve traveled further than you actually have. You can either fly to the small airport located right in town but these can get crazy expensive. Another option is to drive from Miami which will take you about 3.5-4 hours without any stops. However, I will go into which Keys are worth stopping at as this is one of those bucket list drives that people romanticize.

There are buses that have daily departures for a simple Key West day trip from Miami which are an awesome option if you just want to get there without driving or stopping. For as low as a $50 roundtrip on a Greyhound, you can snooze until the very last Key. Lastly, if you’re taking a cruise in the future, a lot of ships stop there too.

When you get to town, don’t use a car unless you’re venturing to a beach a little further away. Most of Key West is walkable but you can also utilize the free shuttle that takes you around town. Another awesome option is renting a bike in town which not only allows you to get some exercise but also covers more ground in a shorter amount of time.

Some common distances for popular Florida road trips:

• Siesta Key to Key West: 370 miles
• West Palm Beach to Key West: 230 miles
• Miami to Key West: 160 miles
• Key Largo to Key West: 97 miles
• Marathon Key to Key West: 50 miles

People & Safety in Key West

I met a couple of locals working in restaurants and bars. People living in tourist destinations are usually friendly and that’s exactly what I experienced there. All others are tourists so prepare to come across a lot of characters.

Key West is super safe. It can get rowdy at night with all the drunks on Duval Street. When you’re in crowded places like where you watch the sunset, for example, use common sense not to get pickpocketed.

Food in Key West

There is a lot of good food stops in the area but Key West is pricey so plan well. Since the island is little, you will often find the same recommendations on a lot of websites. My favorite picks for the area are Grand Vin, a wine bar serving delicious cheese plates, Santiago’s Bodega, an amazing tapas place, or my absolute favorite Key West Cuban Coffee, the best spot for food and some strong coffee!

Perfect Things To Do On Your Weekend in Key West

Drive through the Keys

When I was planning my trip, I insisted on driving to Key West from Miami while stopping at some landmarks along the way. It was one of those romanticized ideas in my head that I always wanted to do. A convertible car, palm trees, and crossing long bridges all the way down. Well … it was that but wasn’t actually as cool as I imagined.

When I was doing my research on multiple travel blogs, many “Ultimate Lists” for the Key West drive from Miami make it seem like there is an overabundance of jaw-dropping activities on the way there. There are a couple of spots that you can enjoy for a little and unless you have a lot of time and can break up the drive into two days just pick a couple not to waste time. Here are the most popular highlights for your drive:

• Key Largo: A little over an hour from Miami, you’ll find John Pennekamp Coral Reef State Park. If you like snorkeling, glass-bottom boat tours or just walking around in a nice park make a stop here. There are two cool restaurants in the area, Sundowners known for its sunset views and Mrs. Mac’s Kitchen, a cool bar covered with license plates.
• Tavernier: The next stop is just 20 minutes away. It’s a famous Key Lime shop called Blond Giraffe. Key lime pie comes from the Florida Keys so it’s a cute and cheesy thing to try in this lime green store.
• Islamorada: Another popular spot is Rain Barrel Village, which is a little collection of art stores and shops. It’s a small stop for trinket shopping. There are giant sculptures outside of it too. For your half-way point treat make sure to stop for a brew at Florida Keys Brewing Co which has a super groovy beer garden. The one thing I loved in this area was Morada Bay Cafe, a beach restaurant with delicious food a unique dining atmosphere. I actually stopped here on the drive back from Key West for dinner, right before the sunset and I highly highly recommend doing it that way. Oh and the last thing people go nuts for here is feeding some fat tarpon fish at Robbie’s. I liked the bar area better than the creepy fish and I enjoyed some birds at the little port instead.
• Marathon Key: People recommend staying in if you want to break up the drive and you can find the Turtle Hospital that rescues the hurt little buddies.
• Then you will cross the Seven Mile Bridge.
• Bahia Key: Right before reaching Key West, stop at Calusa Beach which is a stunning spot of light blues and turquoise waters with some vibrant green palm trees.
• Bonus: There is a cool little bar a little off your path called No Name Pub.

So with all that said, do I recommend driving to Key West from Miami or skipping this part and just heading to there by plane or by bus? It’s a tricky call. If you have the time and reading about the stops above made you smile, then take this US bucket-list drive there. The views along the way are really really nice so just that aspect of it is worth it. However, if know that super touristy restaurants and feeding fish isn’t your thing, spend some extra time in Key West instead.

Southernmost Point of the US

I’m not listing this as the first activity in Key West because it’s the most exciting one but just to get it out of the way. It’s a bouy at the end of some residential street and there is a line of 40+ people waiting to take a picture with it. It’s 93 miles away from Cuba which makes people go wild for some reason. Aside from being a picture spot, there isn’t much to it.

Watching the Sunset

There really is something extremely magical about sunsets in Key West so you should make it a priority to see one. The most known spot for it is the Mallory Square area which floods with people every night for the sunset. They have a little celebration and people gather to admire the amazing colors in the sky. It’s beautiful but crowded.

Another popular option is taking a Sunset Sail with multiple companies offering an open bar and a music option with it. Then there is Sunset Pier at Ocean Key Resort. People also like Truman Waterfront where you can enjoy a sunset without the crowds, sometimes you can find a local market there too. Other good places include the super long White Street Pier or Historic Seaport with boats as your backdrop!

Duval Street

This is a famous party street in town with all the bars and restaurants. During the day it’s fairly “quiet” but still keeps the atmosphere for a party town. It does have some cute shops and pretty buildings on it so you should experience this rather popular side of town.

At night it gets rowdy with all the music in the bars and balcony drinkers. The more known stops here are Sloppy Joe’s, The Rum Bar, The Smallest Bar, and Green Parrott. If you’re up for an adventure stop at Garden of Eden which is a clothing-optional bar.

I don’t think it’s technically legal to drink in the street but a lot of people do out of plastic cups. If you get too annoying or drunk you will get a ticket though so don’t be that guy.

Hemingway Home

Do you love cats and old mansions? I love them both and I can’t think of a better combo. When I heard that Hemingway had a mansion in Key West and that there are like 50 cats that all have 6 toes, I was like “Sign me up.” I bought my ticket and explored the beautiful grounds. It was worth it but I’d also recommend getting a guide there to actually learn something.

Fort Zachary Taylor State Park Beach

I love this spot. It’s a nice beach in a park-like setting which makes it a very unique spot for this area. You can get some food and drinks from a little shop and take great pictures with those travel signs. There is more than just the beach there, you can also bike, fish or paddle. Find the most recent list here.

Smather’s Beach

Located in a much more quiet area of town, I enjoyed this beach for its tranquility. There aren’t that many people around so it’s a perfect spot to take a stroll and relax for a little. Note, it’s close to the airport. If you’re an enthusiast of watching planes land and take off like I am, this is a great spot for that.

Historic Port Area

The whole port area of Key West is just amazing. There is something special about ports in any part of the world so whenever I find one, I make sure to spend some time exploring it.

Simply walk around along the water and find some good bars, cute shops, and just soak in the atmosphere of Key West.

Dry Tortugas

Technically this is not in Key West but the boat will take you to this rather unique destination. It’s a state park with a fort but also some secluded beaches, tons of snorkeling options, and of course turtles. I did not get to go on my trip but one day I shall return.

Here is a map for you too.

FREE downloadable guides for Weekend in Key West

Key West is a great relaxing destination. There isn’t a ton of things to do in town but you’ll be going there to enjoy the “island” lifestyle. You will eat some good food, probably drink a lot and enjoy the beach. There is the possibility that you can only spend one day in Key West but that will only occur if you’re on a cruise ship. If that’s the case, just check out my top things to do there and pick the ones that suit your timeframe.

Whether your weekend in Key West is a two or three-day stay, I prepared a detailed itinerary for both!

Perfect Two Days in Key West

As mentioned, in my opinion, a simple day trip to Key West from Miami is not enough. Two days is a great option for the place although you can easily relax for a week there. However, most of the highlights can be seen in two days.

Perfect Three Days in Key West

If you’re staying for three days, your first two days will look like the two-day itinerary. On day three, you will have some options for a unique experience in this beautiful town.

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As a major enthusiast of anything tropical and warm, I was skeptical about whether visiting Montreal in January will a good choice. Despite the cold, I found this city to be an amazing spot for a long weekend getaway. I explored Old Town, saw all the major attractions, and ate some crazy delicious food. The moral of the story is that you shouldn’t be afraid of visiting places off-season. They can be just as magical at half the price and half the crowds. Check out my Newport off-season guide or the Cape May one for other off-season adventures.

In this 3-day Montreal itinerary, you’ll find all the logistics you need to visit, cool things to do in town, and most importantly, a downloadable itinerary at the bottom of the post.

Favorite spot? Old Port area only because I love ports in any city.

Favorite food? Everything is delicious in Montreal. No joke.

Favorite memory? Having a beer in a rooftop hot tub in -20C weather.

Let’s get to the logistics of visiting Montreal

Montreal is a vibrant and culturally rich city located in the province of Quebec, Canada. With its French-speaking population and rich history, Montreal offers a unique blend of European charm and North American modernity. From the historic cobblestone streets of Old Montreal to the towering skyscrapers of the downtown district, Montreal is a city full of surprises. Whether you’re interested in exploring the city’s rich cultural heritage, indulging in its delicious cuisine, or simply taking in the beauty of its many parks and green spaces, Montreal has something for everyone. In this itinerary, I’ll take you on a three-day tour of some of the city’s most interesting and exciting attractions. So come along and discover the best of what Montreal has to offer!

Suggested length of stay

While three days is a good amount of time to get a taste of Montreal and see some of its top attractions, the city has so much to offer that you could easily spend a week or more exploring everything it has to offer. If you’re short on time, a long weekend or even just a few days can be enough to get a feel for the city and see some of its highlights. However, if you have the opportunity to stay for a longer period of time, you’ll be able to delve deeper into the city’s culture and visit some of its more off-the-beaten-path neighborhoods and attractions. Whether you’re in Montreal for a short visit or an extended stay, you’ll find plenty to keep you entertained and engaged.

Navigational logistics of Montreal

The main airport (YUL) is conveniently connected to the city center via 747 bus for $10 with an included 24-hour public transport pass for your additional connections. It is convenient because it runs 24/7 but it could be a long commute, anywhere from 45 min to over an hour. A taxi will be significantly more expensive, with a fixed rate of $40 plus tip, but if you’re traveling with a group, it might be worth splitting the fare.

Do yourself a favor a buy a multi-day metro pass based on your length of stay. It will save you a ton of money if you’re planning to see a lot of the city. If you took the bus, don’t forget that the first 24 hours are included with your ticket. Use that up before you purchase the next one. The metro is a very straightforward way to get around and the city in Montreal.

Uber is also a great option if you need to get somewhere quickly. I took a bunch of trips at night to dinner restaurants and enjoyed getting to talk to the locals.

People in Montreal

Sit a bar and you’re almost guaranteed to start a conversation with the bartender or a local sitting next to you (assuming you’re going to the less known places). People are super friendly and are happy to get to know you and share their life stories.

At one of the bars I visited, I ended up talking to a person next to me for quite some time. After having a wonderful conversation, I ended up finding out that he’s actually the owner of that particular bar and a couple of other locations. He gave me a good low down of the good spots nearby sharing some tips you wouldn’t find in a top ten things-to-do list. You never know what you can learn from a stranger 🙂

Safety in Montreal

Montreal is super safe. I wouldn’t completely let your guard down as tourists are the prime target in any city, but don’t feel like you need to be anxious during the day or even at night.

A travel companion of mine during the trip ended up losing their passport while walking in the city and we had to go to the police station. The whole process of getting the police report was a very friendly encounter, in spite of the policeman not speaking English. Despite being a stupid tourist at that moment, the police were very friendly and helpful with the whole situation.

Food Stops in Montreal

Montreal is described as a foodie destination in any travel guide or blog you’ll come across. Whenever I see that title, I get slightly annoyed as my expectations end up being extremely high. I feel pressure to hit the best spots and see what the hype is about. Remember though, to find the good spots, don’t go to the first one you see on the main road. Instead, walk 2 blocks to the side and find a smaller joint with locals inside. That’s where the gems are. But don’t fret, Montreal lives up to the foodie expectation and more. I don’t think I had one bad meal throughout the whole stay.

A food tour is essential in this city. Not only will you get to walk around the city and get a little history but the places chosen for these (quite pricey) walks tend to always be delicious.

Hotels/Hostels

Montreal could be your boujee destination or a budget one depending on what you’re comfortable with. There are many places for you to choose from so choose your budget and pick what aligns with your expectations.

By now you should know that I’m the queen of hostel recommendations. In Montreal, I took the middle road by staying in a private room in a hostel. Yes, it is a little more expensive than a shared room, but with this option, you get the privacy you’re looking for but still all the amenities and social vibe that you won’t get at a standard hotel. M Montreal was the perfect place for a couple of reasons. First, we got upgraded from a small private room to a suite at arrival, then the place offered daily activities such as tours for the guests and oh, the best part? There were two hot tubs on the rooftop, an awesome touch for -20C weather during that weekend. That made my perfect day in Montreal.

Sightseeing

There is a TON of things to see in Montreal during the day. At night, there is no shortage of party activities as well. Whether you’re visiting during the summer or winter, you certainly won’t be bored in your hotel room.

Another good thing is that the city offers a bunch of activities such as organized tours and many festivals throughout the year, so every time you visit there is always something new to see.

Montreal is full of awesome things to do. From historical neighborhoods to more modern “too cool to be mainstream” spots. There is always something happening in the city like a festival, pop-up market, unique art event, or an underground concert. It’s a city you can’t just visit once. It needs a couple of different perspectives: the summer outdoorsy scene, a winter snow exploration as well as a stereotypical bachelorette party weekend. I am in love with all that the city has to offer and I CANNOT wait to return.

Perfect things to do on your Montreal Itinerary

Below I will go into detail about each of the places you’ll see on your 3-day Montreal itinerary. However, don’t forget to download the complete 3 day plan at the bottom of this post!

Old Montreal

This charming old area of the city is a must-walk-through on your first trip to Montreal. The whole vibe there is very European, classic, and simply nice to soak in. It’s located close to the port too so you can do both attractions in one shot.

A couple of notable stops in this area are Rue Saint-Paul, the main shopping street in the area, Place Jacques-Cartier, a nice little town square, and Bonsecours Market, an older market that is now a shopping mall with some overpriced boutiques.

Make sure to venture into the little nooks of this part of town as you might find something totally unexpected. I found an awesome light installation on a sidewalk while walking on Rue Saint-Dizier. The lights changed as I jumped on them and the music paired with it was just perfect.

Notre Dame

This stunning basilica is a major highlight of the Old Town area. It is truly a gothic masterpiece. Whether you are stopping in for a mass, quick prayer, or just simply to admire its beauty, you’ll be left in awe. The entrance fee includes a short tour so make sure to take that to learn a little more about this beauty. John Paul II declared this church as a basilica in the 80s.

The Old Port

This whole area is great during the day but it’s even more beautiful at night. There is even a small ice-skating rink if you’re up for it in the brutal cold. The Ferris wheel is perfect for observing the city from above.

That whole promenade area is often a site for festivals or other outdoor events. Always check the official website of events to find out what Montreal has planned for your weekend there. You’ll be surprised how obsessed that city is with festivals.

Old Town Food Finds

After old-town exploration, there are a couple of great places I found for food and drinks that were not total tourist traps. Since I am Polish, I always try to scout a good polish restaurant in interesting places. I stumbled upon Stash Cafe in that area and I was quite impressed with the authenticity of the food.

Another place I really liked for a beer was Pub BreWskey. Although you will find it in a lot of online recommendations, their beers and poutine were pretty good for the hype.

Plateau & Mile End

Plateau is where you’ll find the hipsters and the cool wall art. It’s a very hip area with a ton of art, boutiques, and cafes. Basically everything you’d expect from a gentrified upcoming neighborhood.

The murals are all over the place but if you’d like to know more about the artists and see some less known ones, there is a bunch of walking tours offered throughout the city.

Food Tour in Mile End

My favorite part of that area was the food tour I took. Our guide was very knowledgeable, fed us some tasty foods and we learned some history along the way. These tours can be pricey for a budget traveler but if you have a short amount of time in a place, this is one of the things worth investing in. I chose the Local Food Tours company and I was very happy with their route. What’s nice is that they list all their tour locations on the website. I highly recommend taking the tour though, as you will not be able to learn everything on your own.

Mount Royal Park

Near Plateau, you can visit a huge park that will give you some stunning vistas from above. The famous Kondiaronk Belvedere has one of the best views.

The park also offers outdoor activities all year round if you’re interested in getting some exercise into your trip. For example, in the summer you can paddle boar or in the winter you can cross-country ski there.

Be sure to head to the far side of the park to find Saint Joseph’s Oratory which is a stunning dome church.

Other Notable Activities

When in Montreal, you’d normally just divide your exploring by the neighborhoods to make life easy. Some other spots you can find outside the typical tourist paths: Atwater Market, located a little further out but will provide you the local groceries and finds that you can’t find directly in the city center, Museum of Fine Arts for some classical or MAC for contemporary art, Lachine Canal for some scenic bike riding, Bota Bora, a famous floating spa, Jean-Talon Market, a local market in Little Italy or a beach in the summer called Plage de l’Horloge.

Eat, eat and drink

Montreal is the place to sample a lot of different foods. The quality is usually superb. And yes, don’t forget to get at least one poutine, but there are so many other options all throughout the city.

Legalize it

Don’t forget that Montreal’s recreational use of marijuana is legal. If that is something you’re interested in exploring there, you’ll be happy with your selection. Please please please don’t be that idiot that tries to bring it back to the states. You know very well that you cannot and it will not be worth the headache of getting caught.

If smoking the goods isn’t your thing, Stogies Cigar Lounge was a great spot I found in town with amazing service and helpful tips if you’re not a cigar connoisseur.

or take it off …

It’s not a secret that Montreal nightlife is very known for its strip club scene. A small google search will provide all the answers you need.

Montreal is also a very popular destination for clubs and its nightlife. Grandma here tugs in around 11 pm at the latest during winter months, so I couldn’t tell ya where the good spots to the party are. However, there are pros out there who know more about the subject matter than I do.

Map for you to save

Perfect Montreal Itinerary: FREE Downloadable Guides for your stay

Three Perfect Days in Montreal

Three days is the sweet spot for this city in my opinion. Not only do you get to do the highlights of the most popular things the city offers but you’ll also spend some extra time in the places you liked. With three days, you can absorb a little of the culture and fully understand why so many people come back to this city over and over.

If you have any suggestions on how to make this perfect itinerary even more perfect, comment below! I would love to hear your perspective.

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