Havana Itinerary: The Reality of Traveling to Cuba
You’ve probably romanticized Cuba by looking at pictures of vintage cars, old ladies smoking cigars, green mojitos, salsa dancing, and colorful colonial buildings and thought, “I have to go there at least once in my lifetime.”
That was certainly me.
Cuba was always on my bucket list so when I turned 26, I decided to buy myself the perfect birthday gift: a ticket to Havana. Although I was more or less familiar with the situation there, I admit that I didn’t dig much into the ethics or realities of Cuban travel. When I got there, however, like many other travelers, Cuba broke my heart. The things we glamorize are a sad reality of life for the local people. It felt wrong to take “amazing” photos with the background of poor living conditions, lack of basic products, and the government’s role in people’s lives. And don’t get more wrong. All the locals I have met there were the sweetest and most welcoming people who made the best out of their situations. However, hearing stories of what day-to-day life looks like, made me stop looking at Cuba through the “cars and cigars” kinda lens.
Should you travel there, is completely up to you. On the one hand, you want to be able to contribute to the economy but on the other when you know that your money will further feed the government, you might not want to feed. I traveled there in 2018 and although a lot has changed since then, tourism is back and many people continue and will continue to visit this place. I am not here to preach whether you should or should not visit. I am simply here to show you what traveling to Cuba entails, what you should expect, and show you what places to see. This Havana itinerary is honest and detailed and I hope it helps you to make your decision.
What you will find in this guide:
- All logistics needed for your Cuba travel
- A realistic look into popular attractions
- Some hidden gems are scattered along the post
- Free downloadable itineraries for 3 days in Havana
- A map with all attraction pins
Logistics of Traveling to Cuba
Traveling to Havana Cuba requires a little bit of preparation, especially for US citizens. Having the correct plan and all required paperwork is absolutely necessary. There are some providers that arrange your paperwork for a fee but I personally think you can figure it out by yourself. I visited in 2018 and had no trouble crossing the border into Cuba or returning to the states. No one asked me much about my plans or what I did there. However, it is absolutely essential that you do everything correctly. Also, remember that things constantly change. Always double-check that the requirements are in agreement with sources like government websites.
Visa to Cuba: US citizen entry requirements
Here is a summary of how to get to Cuba as an American citizen.
- Can Americans go to Cuba? Yes, US travel to Cuba is legal.
- Booking a flight is possible from major airports in the USA. Where is Cuba located? Well, it’s only 90 miles from the south of Florida. New York and Florida have direct flights too, making your connection super easy. As a US citizen, you will only be able to fly into Havana.
- There are 12 categories to select your travels from. Tourism is not a reason for travel. The most popular declared category is Support for Cuban people. There are more like education, research, religious or journalist activity. It’s a self-selected category so pick one that matches your visit the most. You will declare this at some point in your travels, it’s not an official document.
- When traveling under the Support for Cuban people category, you will need to stay at a Casa Particular. I booked my stay through booking.com and stayed with a local host. For any other locations, check this Restricted List of places in Cuba that US citizens cannot stay at.
- You will also need a printed-out itinerary with plans for your entire stay. I made sure to have one but no one honestly checked it. You’re required to keep it for 5 years upon return.
- A Tourist Card can be purchased from your airline at the airport. I flew Southwest from NYC connecting at FLL. They had little booth stands at the FLL airport at which you purchased your card and stated your travel category. This is your Visa to Cuba.
- Travel Insurance to Cuba that is specific to Cuba is also required. When I purchased the tickets through the airline, it was included in the price. Check if yours is as well and if not, you can purchase it upon arrival at the airport.
When you arrive:
- Cuban currency is complicated.
- Take enough cash for your trip as your American cards won’t work there. Estimate a budget based on your type of travel and convert it to a CADECA which can be found at the airport, hotels, or other places in town.
- As of 2021, the USD is no longer accepted at the government exchanges so grab some euros as a backup. You can exchange it informally and actually get a lot more than a standard 1:24 exchange.
- Internet connection is hard to get unless you purchase a special card. I would simply plan to “disconnect to connect.”
- Finally, you might think Cuba is a cheaper country. Well, it’s absolutely not.
There are two currencies, CUC or convertible peso, and CUP Cuban peso. As a tourist, you will have to use the CUC with a 1:1 conversion to an American dollar.As of 2021, this is not the case anymore. The country now uses only the CUP at a 1:24 conversion rate. Although if you sell it unofficially you might get a 1:80-100 rate instead. - You can’t get Cuban currency anywhere else but Cuba.
- If you have a US-based debit/credit card, you won’t be able to use it there due to the embargo.
Suggested length of stay in Havana
Is three or four days enough time to properly visit just Havana? Well, kinda, but if you’re planning day trips and other areas of the country, I would plan to spend at least 7 days in Cuba. There is a lot to see there and aside from Havana, you’ll want to take a couple of day trips out. Obviously, that doesn’t sound like much but remember that this is a short-travel kinda blog 🙂
Airport Jose Marti in La Habana, Cuba is located about 30 minutes from the city center of Havana. You will need to take a taxi to town. I asked my host to arrange a pick-up for me which was a fixed rate and took me straight to the casa without any confusion. It was around $20 which should be fairly comparable to what random taxi drivers will charge you at the airport. Due to recent changes in the currency don’t bank on your US dollars being accepted. You might be ok with them (ask your drivers) but having some Cuban pesos or euros won’t hurt.
Most of the city is walkable if you’re staying in the main area. For touristy sights, you will be able to get by without a taxi. If you want to venture out a little further, there is an abundance of taxis in the streets always waiting for you to hop it. Bonus, they are mostly vintage cars that you’ve seen in the photos therefore every trip in one makes you feel like you’re in a movie.
Other modes of transportation are Colectivos which are shared rides and can be a more budget alternative. Ask your host to arrange one for you. Viazul is the bus line that will take you all over the island at a pretty good rate. Coco-taxis are yellow tuk-tuk-like transports.
If you’re staying with a host, make sure to ask them to call you a taxi. That way they will make a little money for a referral and you’ll get door-to-door service.
People in Cuba
People are nice. Truly nice good people. It’s actually kinda fascinating how amazing and warm they are with what kind of treatment they get from their own government. And no, Cubans are not brainwashed. On the contrary, they are very informed about what is happening in the world. At least that’s what I experienced with those who hosted me and took me on tours.
Is Havana safe?
Cuba is generally very safe and you shouldn’t be afraid to walk around. They have low crime rates because of the consequences you can face when committing one there. Girls will get cat-called here and most locals consider it a compliment rather than an insult.
Beware that when you’re inside the city, there are local scammers (Jineteros) near the main tourist places. For the most part, they are not dangerous just very sneaky. Simply knowing the most common scenarios should make them obvious when they start happening. Here are some very common scenarios. I promise that you will encounter at least one of them there.
- “Omg! You totally don’t look like a lost duck with your map and a new Nikon. Well, guess what, if you follow me I got good cigars at someone’s house for sale” – Umm, hard no.
- “Oh, it’s your first day here! Guess what lucky guy and gal! There is a cool festival today that you should totally attend and I will show you exactly where it is.” – This actually happened to me. A very friendly individual became not so very very friendly when I refused to follow him to this magical festival.
- “It’s my birthday!” or “Someone died today” or “I’ll buy your coffee!” – All these end in someone mooching off of you for food or drinks and getting their commission at a friend’s bar.
- “My baby needs milk” – Really? Come on people. Don’t use baby guilt on strangers. Your nonexistent baby doesn’t need a $30 milk that your will split with your milkman.
- “Museum/restaurant is closed today my friend” – K thanks for letting me know. I will check for myself first before believing you.
Yes, I know what you’re thinking, these seem so silly, how would I even fall for them? Well … these professional hustlers are usually very good at their jobs and it’s easier said than done to avoid them. I mean let’s now talk about my $100 blanket that I bought in Fes fully knowing that a $100 blanket is a scam in Morocco. All I’m saying is that at least knowing the scenarios and having a mental check with yourself when you’re in one is a little better than blindly going in. But overall Havana is a safe place.
Gifting
A common practice among travelers is bringing gifts for the locals as certain basic goods are hard to obtain in the rationed economy. I personally did not bring any and from reading more on the subject, it seems to be a mixed opinion among travelers.
On the one hand, you want to help out the locals but on the other, you’re enabling a culture of expectations each time someone visits. If I could do it again I think I would bring something small for my host and maybe a couple of toys for the kids. It’s a tricky call but it’s something nice to do.
Note as of 2021, this should be researched further as supplies became more and more needed over the past year. If you’re planning to go, this should be important. For a very broad example, bring things like painkillers, common first-aid stuff, hair dye, or make-up.
Food in Havana
Food is a tricky subject in Havana. Some people have horrible meals, while others swear that it’s one of the best they ever had. I personally fell right in the middle. The food was good but it wasn’t something I particularly remember having blown me away. I’m also from New Jersey where Cuban food is widely available and super delicious. My approach was to try it all: at the casa, at a small local restaurant, the more “hip” one, and finally some street food.
Don’t forget that you’re going to a place that doesn’t have access to the same amounts, spices, or varieties of foods that someone for example in the states does. This doesn’t necessarily mean that the food will be bad but it will certainly limit your options. Make sure to have a good mojito too.
Hotels/Hostels
As an American, it is recommended that you stay in a Casa Particular or a locally owned B&B style accommodation. If you’re traveling under the “Support for Cuban People” category, this should be your option. You can book those online prior to your visit. However, if you’re feeling adventurous, you can book them on arrival in town. Lastly, if you’re planning on choosing another option, make sure that it’s not on the sanctioned list.
I loved my experience at the Casa I stayed in. Our host made us breakfast every morning and gave us some local tips on what to see. It was a more authentic way of seeing the country. She also helped with our money exchange as well as arranging a tour for one day of our stay.
Additionally, a lot of travelers choose to pick hostels in Havana thus a more social way to see the city. I would check out Hostelworld to find the best match for you. I wish I stayed in one to have gotten to know more travelers. However, hostels are not for everyone so unless you’ve stayed at one, I wouldn’t recommend Cuba to be your first experience with that kind of accommodation.
Sightseeing in Havana
There is a good amount of things to see in Havana. In comparison to a typical trip, the whole city itself is a sight. In addition to exploring, make sure to set time aside for soaking in this extremely unique and vintage place. People watching, drink sipping, and strolling in the old streets will be some of your favorite memories from there. Try to talk to locals but don’t touch on the topic of politics unless they choose to talk about it.
Things To Do On Your Havana Itinerary
Havana is charming and beautiful in its own way but remember, don’t romanticize people’s actual struggles. It’s easy to be impressed by the vintage cars, colorful buildings, and just a different way of living. However, when you dive deeper into why Cuba is the way that it is, all this stops being magical. It was a difficult place for me to visit and I felt wrong using its hardships as a background for my pictures. I got to talk to a couple of locals that were willing to share the realities of their lives. Despite it breaking my heart a little, the Cuban people were the ones that made my trip amazing. I hope you find things you love there as well without being blind to the realities of this place.
Old Havana
Habana Vieja is the main tourist area of the city filled with landmarks, restaurants, music, dancing, and everything else that makes it one of the most recognizable places to travel to. This is the area I would recommend staying in or at least nearby at a casa particular. Note that it’s very touristy and not as representative of actual living conditions, however, it’s something you should see.
There are numerous landmarks within this part of town that I will cover below but this part of town is an attraction all within itself. Make sure to roam around the streets and note the patched-up tourist buildings vs. the real way of life a couple of blocks away. As expected, the scammers are the most active here.
If you’re going to do any activity there, make sure to do a free walking tour. A quick history lesson from someone who lives in Havana is a must. I used this company for my Havana tour and I was very happy with everything I saw on the tour.
Obispo Street
Obispo Street is simply a long pedestrian street dedicated to all things tourists. I walked it at least once a day as it connects all the major sights in the city. It’s full of little stores and historic buildings. Although it has some street restaurants, I didn’t love the quality of the food there. At night, find some lively dancing and music shows. It’s one of those streets you just have to visit.
The places every travel guide writes about
You must have heard about Bar Floridita, Hemingways spot for a good daiquiri, Bodeguita del Medio where Hemingway (again) liked his mojitos, Sloppy Joe’s Bar long bar, La Guarida’s famous rooftop dining or Tropicana for the famous shows. If you’re going to visit, it for sure won’t be an authentic experience but I would at least try to see one of them. Remember that famous places are usually famous for a reason.
Plaza Vieja
I loved this square. It has colorful (updated) buildings, street artists, and cute bars with balconies overlooking the plaza. Aside from the bars, little vendors, and occasional street shows, there isn’t much to do there but for some reason, this was one of my favorite places in the city. I recommend grabbing a drink and a bite on one of the balconies overlooking the plaza too. It lets you see everything from a different perspective.
If you want to experience something unique, make sure to check out the Cámara Oscura located in one of the buildings in the plaza. It’s a light trick device that gives you a 360 view of the city. There aren’t many of them left in the world so it’s a very unique experience to see one. You will also get unmatched city views from the rooftop.
Castillo de la Real Fuerza
It’s a fort in Havana with a museum inside. I only explored the outside during the walking tour but if you’re into forts and that stuff, they offer tours for around $10. If you take a free walking tour, this will be one of the stops going into the history of this place.
Plaza de Catedral
Speaking of Plazas, this one has a cathedral hence the name. It’s one of the historical plazas in town and it attracts a ton of tourists. As the name suggests, there is a cathedral in this place. The inside of it is very beautiful so make sure to take a peek inside. There are a couple of restaurants and local vendors in the plaza worth a couple of additional minutes of your time too.
El Capitolio
This capitol building is a stunning piece of architecture. It’s inspired by the Capitol Building in the US. You can simply stroll around and admire the old cars, parks, and colorful buildings right next to this impressive structure. Fun fact, you can actually enter this building, something I wish I did. The admission ($3) includes a free tour with it.
Havana Art Scene
Gran Teatro de La Habana
This is a beautiful theater in the city. The building and its surroundings are beautiful from the outside. Very elegant and different for this city. They offer tours for a little under $10 so I would recommend doing that. The history is quite interesting and complicated. Additionally, you can catch the ballet, opera, or other shows at cheap prices (compared to NYC). Make sure to see this place during the day as well as at night.
Fine Arts Museum
The museum has two locations, one near Prado in Havana Vieja housing international art from world-famous artists like Goya or Velazquez. The second location is the Palacio de Bellas Artes near Parque Central. Here you will find Cuban art. I regret not visiting because when I saw the uniqueness of the art online after my trip, I really wish I got to see it in person.
Fabrica De Arte Cubano
On a whole different spectrum of art, here is Fabrica de Arte. I will let this review speak for me because I could not have said it better.
Callejon de Hamel
A random hidden gem of the city! I stumbled upon this place totally by accident. It’s basically an alley filled with cool art by an artist named Salvador Gonzáles Escalona. They have some local music and shows on Sundays around noon. It’s a little out of the way but the detail and quirkiness of the art is worth making a trip there.
Fusterlandia
Jose Fuster, another famous Cuban artist, created this gem in the 70s. Inspired by Gaudi, he transformed a whole neighborhood into a piece of art. If you visit, you’ll immediately notice the Gaudi inspiration in all the intricacies of the tile. However, it is very clear how much Cuban culture was incorporated into it as well. Here is an interesting article about this place that I recommend reading.
Vintage car ride
This is the most touristy Havana thing you can do but why wouldn’t you?! Did you see those cars? They’re beautiful. You can take a guided tour where the driver will explain to you each landmark around the city and that should cost you around $20 per hour. Or you can use it as a regular taxi to get you somewhere you want to go. I personally hired a driver to get me to the beach and then pick me up, all in a pink convertible. Even though it costs me some money, it was one of the main highlights of my trip.
El Malecon
This is a long esplanade along the water that stretches for a decent distance. You will see a lot of the locals fishing and enjoying their afternoons. This is a very “Cuba” spot. A beautiful sunset cannot be missed at least once during your trip from there. One of my favorite things I discovered off this street was an old-style Russian restaurant Nazdrovie. It was super random but the food was delicious there and the balcony dining had the best views.
Hotel Nacional de Cuba
Historical gem of Havana. This hotel was built almost 100 years and was a staple of class back in the day. A bunch of famous people stayed there and there is a TON of history surrounding this building.
I skipped the history and opted out for a cold mojito in a beautiful garden. It was classy and divine 🙂 A lot of tourists love the cigar shop inside too. As a non-guest, you can wander around the lobby and explore the property grounds that are filled with peacocks. Note that Americans cannot stay in this hotel.
Day Trips from Havana
Playas del Este
There are no beaches in Havana, Cuba so if you want that tropical baby blue water atmosphere, head to Playas del Este located only about 30 minutes outside the city. The place is beyond stunning and the water was crystal clear and super warm. A couple of beach restaurants offer live music and good food! I would say this is a must if you’re not going to other beach areas on the island.
I personally hired a driver for the day in a bright pink taxi. I found him in a taxi stand and paid him $40 to take me to the beach and then back along with some additional drives around the city. Honestly, I probably overpaid for this but this was the one thing I wanted to do on my trip there.
Varadero Day trip from Havana
Varadero is another beach town with many all-inclusive resorts and beachfront properties. There are a couple of ways to do this day trip: you can hire a car, take a bus or pay for a day tour to an all-inclusive resort. I opted for the third option because the price of that option was very comparable to a private taxi and I did not want to deal with the bus. I asked my casa host for an agency contact to book this trip the day before and made the decision to explore this area of the island.
The day started off rocky as our pick-up was over 1 hour late. Then the little passenger bus stopped along the way for some viewpoints. When we arrived at the all-inclusive, they separated us into small same-sex groups and put us into rooms where we were able to leave our things and change. Then we spent the day with our all-inclusive passes enjoying the beach and resort. It was very touristy and very curated but it allowed me to spend a day on a beautiful Cuban beach without a worry in the world.
Havana to Vinales day trip
Viñales is an amazing 2 hour trip into the STUNNING valley of mountains and tobacco fields. It’s certainly not close to the city, but it’s a favorite of day trips from Havana if you’re not venturing too much into the island. For my day trip, I used Discover Viñales and I loved the private tour they offered. Note, that it was super pricey. In addition to the day trip to Vinales from Havana, they do offer a couple of other Cuba tours. We got to see the stunning valley, a cave, a cigar factory, a botanical garden, a family tobacco farm, each lunch on that farm, and then end the day with a drink in a restaurant overlooking the valley.
Although seeing Vinales in one day is doable, I would certainly recommend spending a night there. The valley is a very unique destination and deserves much more of your time than what I gave it. However, this is one of those major downs of short-term travel. If you find a place you really like, you don’t really have the flexibility to add more time.
Aside from seeing the valley, one of my favorite parts was interacting with our hosts for the tour. The driver and tour guide was super friendly and amazing to bond with for the whole day. They gave us a more realistic perspective of the island and answered a ton of our questions about their day-to-day in Cuba.
Final Thoughts on Visiting Cuba
Cuba remains one of those places that will stick out in your mind. You can choose to ignore the realities and go take your vintage taxi ride, drink mojitos at Hemmingway’s bars and never think twice about what life is like there. Or if you decide to travel you can do it more consciously and try to turn your head to the sad realities of this place.
Rather than simply admiring the buildings of Plaza Vieja and Obispo Street, walk a little further out and look at the buildings that are falling apart. Instead of just taking a picture in that amazing vintage taxi, notice the locals fixing the cars in the alleys with little parts they have and barely afford. While splurging on a meal at La Guardia, don’t forget to notice the ration lines at the regular stores.
I don’t think boycotting Cuba travel is the answer and I also don’t think our money there will make too big of a difference either. The only thing we can do is respect the locals, have meaningful conversations, try to spend our money on more local businesses, and simply be aware of the realities of Cuba.
Havana Itinerary: FREE Downloadable Guides for your Havana Tour
Three full days is a good chunk of time to see the highlights of this amazing city. My three-day Havana plan is full of adventure and on the third day, you will head over to Viñales Valley to see a more rural part of this country. The Valley is nothing like you’ve ever seen and I promise you’ll have a good time there either riding a horse, exploring a farm or simply enjoying the views.
Your perfect day somewhere is not necessarily the perfect life to the people in Cuba. There is a horrible dictatorship there, your money will only help the Cuban Regime have more funds to oppress Cuban People and take every known human right from them and even those rights yet to be known. Source: my life there for 35 years.