The Complete Cuba Travel Guide

Trinidad, Cuba

In March 2019 I went to Cuba and had a blast. It’s become easier and easier to get to Cuba from the United States, but the process is still mysterious to many people. In 2014, Obama rolled back Cuba travel regulations. By 2017, hundreds of thousands of US visitors with no family ties in Cuba were traveling there. And yes- you can still go there (relatively) easily!

Read on to learn more about getting to Cuba, planning your trip, and what to expect – both the good and the bad.

Getting there

Step 1: Determine your travel category

For US travelers, there are 12 tourist card categories for entrance to Cuba. This card is often referred to as a Cuban Visa, although it’s not technically one. It’s good for 30 days of travel to Cuba. None of the categories are purely for tourism, but you should be able to find one that works for you! I traveled under Support for the Cuban People. Learn more about the other categories, including educational or religious activities, here, and this article from Discover Corps has good information on the Support for the Cuban People visa.

If you’re traveling under Support for the Cuban People, it is recommended that you have an itinerary that shows that you will be interacting with the Cuban people and supporting independent activities that strengthen civil society in Cuba. These are all things you’d probably want to do on your trip anyways, so it’s easy to fulfill the requirements! Some examples include:

  • Staying in homestays, called casa particulars (book them easily online here)
  • Exploring markets and meeting with local artisans, tobacco manufacturers, etc.
  • Eating at locally owned restaurants
  • Dance classes and music shows
  • Discussing Cuban society with locals

Here are the ultra-official rules for this tourist card. It is recommended that you have an itinerary before you arrive that shows how you plan to spend your time. Unfortunately, lounging on a beach for 4 days won’t quite cut it. The number one thing you don’t want to do is spend money at military-owned businesses. It’s actually forbidden by the US State Department. You can find the list of businesses and hotels to avoid here.

Many airlines let you pick up the tourist card at the airport when you’re departing for Cuba, so you may not need to purchase it until your departure date. Mine was $50 through JetBlue, which takes us to step 2.

Step 2: Find a flight

I booked an affordable flight from Richmond, Virginia to Havana, Cuba with a layover in Fort Lauderdale through JetBlue. They offer flights to 4 cities in Cuba, and made my booking process very easy! There’s actually a section of the JetBlue terminal just for Cuba flights. Southwest, American, and United also offer flights and provide visa guidance.

JetBlue not only made this process easy, but they included the required health insurance for US travelers to Cuba in the cost of the ticket, and had a dedicated counter at the airport to purchase the necessary travel visa. They could not have made this process easier (besides the mechanical issues on my return flight, but I digress).

Step 3: Get Cuban Health Insurance

Travelers to Cuba are required to have Cuban health insurance. Your regular health insurance will not cover you in Cuba. There will be a booth in the airport where you can purchase this if needed, but your airline may include this travel insurance in the cost of your ticket for ease and convenience. The policy is no more than a few dollars per day.

Step 4: Prepare to bring cash, and maybe change your currency

There are two currencies in Cuba- the Cuban Convertible Pesos (CUC) is for travelers, and Cuban Peso Nacional (CUP) is the local currency. I think that this article by ViaHero explains it pretty clearly. The CUCs are about 1:1 with the USD, but the exchange rate for the local currency is closer to 25CUP to 1 USD.

There is a 3% fee to exchange your money at the Cuban airports or banks. It’s also a closed currency, so you cannot change to it before entering the country. In addition, it costs an extra 10% to change over USD. It may be useful to change your money to Canadian Dollars or Euros prior to entering Cuba.

When I say bring cash, I mean cash. American bank and credit cards simply will not work in Cuba. You cannot use your debit card to take out dollars or CUCs. Make a budget for your trip and bring some extra that you don’t convert to CUCs just in case its needed. When you run out of cash, you’re really out. My friend and I had a detailed budget and left Cuba with less than 2 CUCs in our pockets, but we had $200 extra USD each in case we had needed it.

Lodging: Airbnb

I found Airbnb to be the best way to book homestays in Cuba. At one point, Cuba was Airbnb’s fastest growing market and it’s an easy way to find affordable and comfortable lodging. You can also book homestays upon arrival just by walking around and asking, as well as on a few other websites. Just google ‘Havana Casa Particular’. Airbnbs range in price, and many rooms are available for less than $20 per night! You can find anything from traditional homes to luxury lodging.

Here is a place I stayed in Havana and had a great experience. It’s worth noting that wifi isn’t abundant in Cuba and even if your host offers it, you often have to purchase a government issued wifi card with 1 hour of access. Keep internet surfing expectations low. Many homestays offer private bedrooms and bathrooms and the option to purchase water bottles, beer, and breakfast.

One great thing about homestays is that your host has the Cuba connections that you need to get around. I stayed in 3 different casas particulares, and each owner was happy to assist with taxis to and from the airport, colectivos for travel between cities, restaurant recommendations, and breakfast offerings. Don’t be shy about asking how to get around- they are ready to help make your Cuba trip easy!

Get up to $55 off your first Airbnb booking here!


Cuba is pretty huge! It’s 40k square miles have mountains, the sea, and widespread cities. Unfortunately, there isn’t a good train or bus system to get you about. I got around using colectivos, which are collective taxis. You ride with other travelers and each pay a portion of the cost of the car.

Some cities you may consider include:

  • Havana – Capital City of Cuba with 2 million people and Spanish-Colonial architecture
  • Trinidad – UNESCO World Heritage Town that’s like a time machine to 1850
  • Cienfuegos – A historically french town on the bay
  • Varadero – Beautiful beach resort town with clear waters and yellow sand
  • Viñales – Natural landscape with mountains, hiking, tobacco farms, and more

I would say that you don’t need more than 3 days in Havana and 2 days in both Viñales and Trinidad. I didn’t have the chance to go to other destinations during my week in Cuba, but there is something for everyone! I used Havana as a home base and booked a tour to Viñales while in Cuba because I felt like I had the time.

Trinidad, Vinales, and Havana

My one week itinerary:
Day 1: Arrive in Havana
Days 2-3: Travel to and explore Trinidad
Day 4: Travel back to Havana
Day 5: Day trip with a tour company to Viñales
Day 6-7: Explore Havana

Getting around


I rode with 6 other travelers for 5 hours from Havana to Trinidad in a classic car, and with 3 other travelers for 4 hours when I returned to Havana in a regular taxi. This 180 mile trip could have been 6+ hours on a bus, but a colectivo shortened the journey. My homestay hosts organized these colectivos on my behalf and cost $35 per person each way.

My colectivo from Havana to Trinidad. We fit 7 passengers and their luggage into this classic car! In colectivos I met Koreans, Germans, and Cubans.

I read in some places that the ride from Havana to Trinidad would take 6 hours, and in other places I saw 3.5. This really depends on how fast your driver goes and how many stops you make along the way to pick up other travelers or for a restroom break. I would set aside 5 hours for a trip between these two cities.


Taxi drivers are everywhere, and you’re constantly being asked if you need one. Make sure you set the price before getting in the taxi. Meters aren’t as common here, but asking your host or people you trust how much rides should cost can help you negotiate. Here is a price sign I found in one of my Havana taxis for reference. For example, it should cost $24 CUCs to get to the airport from Havana.

Modern, fun taxis in Havana’s city center. Cuba isn’t all classic cars, but I rode in them more often than not!

Tour Companies

I used a tour company to go to the Viñales Valley and back. The journey was 120 miles and took about 2.5 hours on the large bus. After arranging all my own travel besides this trip, it was nice to be shuttled around safely in a mountainous area of the country and not have to worry about it. A 10-12 hour tour (Ours advertised 10 hours but was longer) can be booked in Cuba or ahead of time through companies such as Cubatur and Havanatur. I pad $67 CUC for roundtrip transportation, lunch, and stops at a tobacco field, cave, and overlook. I’d recommend tour companies for easy excursions, but not your entire trip.


I chose not to travel by bus because colectivos would be quicker. You can get on buses organized through the company Viazul. These bus trips are super affordable, but not all buses are in great shape. I saw one broken down on the highway and all the tourists standing outside. Here’s a guide to how long trips may be on their routes.

Things to do


  • La Floridita is right off of the main plaza in Havana
  • Fabrique de Arte Cubano in Vedado is a warehouse turned art gallery / concert venue with multiple bars and dance rooms. Arrive early to avoid the line. 3 CUC cover charge
  • La Floridita in Centro Habana is considered the cradle of the daquiri and was a favorite spot of Ernest Hemingway. Very touristy, but very upbeat and fun.
  • Plaza de Armas in Old Havana has live music and well cared for historical sights. Can fill up with cruise travelers.
  • The Malecon – While not the shining promenade it once was, the malecon is a few miles long and stretches across the waterfront on the edge of Havana.
Havana from above


  • Playa Ancon – This public beach outside of Trinidad is beautiful, quiet, and offers ample shady umbrellas for relaxing.
  • Disco Ayala – A club in an underground cave. Just as cool as it sounds, but it’s very warm inside. Cover is 5 CUC and includes one drink.
  • National Museum of the Struggle Against Bandits – While I hear this museum is more interesting with a guide, I’m recommending this for the view from the belltower. Costs 1 CUC to access the museum.
  • Casa de la Musica – Watch great live bands perform and salsa dance under the stars.
  • Parque El Cubano – there are many nearby waterfalls in the national park nearby! When I went to one in March, it was barely a trickle and quite disappointing so I don’t want to recommend my specific trip to one, but there are many options!

Places to eat

When I left for Cuba, I heard that the food there would be bland and terrible. Many Cubans don’t eat much meat and spices are hard to come by. I didn’t find that to be the case. While I ate many ham & cheese sandwiches with no seasonings, there are great places in Cuba with great food.

Note- Cuban Sandwiches are not actually Cuban, but Cuban American. You can find those in Miami!


  • El Chancurello – Get the ropa vieja, rice and beans, and a mohito. 5 CUC average.
  • O’Reilly 304 – Spanish tapas in a hip and trendy bar. 12 CUC average.
  • Cafe Archangel – Slow service, good breakfast. Only coffee I liked in Cuba. 5 CUC average meal.
  • Street Pizza – Cubans love this foldable pizza from a street stand. Eat like a local and try some! 1 CUC for a personal pizza with ham.
  • El Dandy – Great tacos, large menu, generous portions. 10 CUC average.


  • La Botija – Not actually serving food 24/7 like they claim, but a very popular spot. Long lines for dinner. Good breakfast options. 5 CUC average for breakfast, 12 for dinner.
  • Cafe Don Pepe – Cute coffee shop, only food is ham sandwiches.

I personally ended up eating a lot of Clif bars in Trinidad due to our schedule, but there are so many fun restaurants with rooftop terraces and live music. You can’t go wrong watching the sunset and eating traditional Cuban cuisine here.

Trinidad from above


Cuba is such a unique country. There are no advertisements anywhere, and all billboards feature government propaganda. Even so, you can feel the life and resiliency of the Cuban people as well as their friendliness and interest in making you feel welcome.

I don’t want to paint a rosy picture and ignore some of the turmoil here. Many parts of Cuba are crumbling and many people live in poverty. People think its romantic that the cities look trapped in time, but this is due to the US trade embargo. It’s trapped in time because it had to be. Sonic attacks happened on the US Embassy just last year. Even so, I’m so glad I went to Cuba and got to experience the country as it is just beginning to open up to the world and experience so many changes. It’s so unique- I still feel like nothing can prepare you for what you’ll experience in beautiful Cuba.

Traveling to Cuba requires a few extra steps of preparation, but otherwise it made for an amazing and memorable trip abroad! Make sure you book some things ahead of time because internet will be scarce, and definitely budget more than enough cash.

Quick Tips:

  • If you speak even a little Spanish, you’ll get by much easier.
  • 2019 is the 500th birthday of Havana and there are celebrations all over the city with a large one planned in August.
  • While the Cuban and US governments don’t get along, many Cubans have family in the US and think positively of the people.
  • The going price for a mixed drink is 3 CUC and a beer is 2 CUC.

If you have any questions about Cuba, please feel free to ask!