Cuba Travel Guide

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Americans and Cubans have been starved of interaction for decades despite being so close to each other geographically. Cuba has always been important to me for many reasons, and seeing this restoration of relations was surreal, incredible, emotional. It was so exciting for me and my family

-Two-time Grammy Winner Eric Oberstein during his interview with AdventureDaze

Getting There


  • Airport – José Martí International Airport (HAV)
  • Currency – Dual Currency System: CUP (Cuban Peso) and CUC (Cuban Convertible Peso)
  • Official Language – Spanish
  • Population – 11.3 million
  • GDP – $77 billion (64th Overall)


Why is This Island Different from All Other Islands?

The largest island in the Caribbean, Cuba spans more than 42,000 square miles and boasts a population of 11.3 million inhabitants.  Christopher Columbus landed on the coast of Cuba in 1492, and from then until the Spanish-American War of 1892 Cuba remained a colony of Spain. The Spanish influence on Cuba is undeniable, with similar architecture, food and of course the language.

That all changed in the early 1900s as Cuba gained its independence after the Spanish-American War and began self-governance. In the 1930s, the existing government was overthrown and Fulgencio Batista took power – first through a string of puppet presidents and ultimately as President himself beginning in 1940.

cuba travel guide

As Batista’s regime became increasingly corrupt, Cubans sought change. This led to the Cuban Revolution which began in 1953 when Fidel Castro and his backers (including Che Guevara) stormed in. By 1959 Batista had been ousted. While the Cubans were initially hopeful that their new leader would bring about more equality and prosperity, Castro introduced communist policies that were aligned with the USSR, who at the time was engaged in the Cold War with the United States. These policies led to events like the failed Bay of Pigs invasion and the subsequent imposition by the United States of an economic and travel embargo on Cuba beginning in 1960. This embargo ultimately resulted in the severing of all diplomatic relations between the US and Cuba.


Restoration of Relations

Beginning in December 2014, Barack Obama and Cuban President Raúl Castro symbolically announced an easing of the historically fragmented relations between the United States and Cuba. Then, in March 2015, the two leaders announced a further easing of relations, permitting American citizens to travel to Cuba for educational and/or research purposes under the permission of a visa.

cuba travel guideSlogans referencing the Cuban Revolution appear throughout Havana


U.S.-Cuban relations are now at an inflection point where travel restrictions are being further relaxed and commercial trade is beginning to open up. President Obama historically visited the island in March 2016, making him the first sitting U.S. president to visit Cuba since Calvin Coolidge in 1928.


Tourism in Cuba

While new to U.S. citizens, Cuban tourism has been accessible to Europeans and other foreigners for years. In fact, 3.5 million people visited Cuba in 2015 alone – 1.3 million of them coming from Canada. Given the relaxed U.S. travel restrictions, there was a 77% increase in American visitors in 2015.  Cuba generates roughly 10% of their GDP from tourism revenues. And while that may sound low, it is a testament to Cuba’s size and presence in the fields of agriculture and industrial production.

cuba travel guideTaking a taxi from Central Havana to our Airbnb


I’m from the U.S. – Am I Allowed to Go to Cuba Now?

Ever since the restoration of Cuban-American relations, it has become far easier to travel to the Caribbean’s largest island. Starting in 2015 there were 12 categories under which you could legally obtain a visa to visit Cuba, including academic programs, journalism, and professional research. However, in March of 2016, the U.S. Government announced even more lax rules whereby Americans may travel to Cuba for almost any reason, as long as they comply with bringing no more than two boxes of cigars back to the U.S.

Today, all you need to do is buy a ticket on a chartered flight (e.g. from Cuba Travel Services or ABC Charters), book an apartment to stay on Airbnb, and that’s it! The charter company will provide you with a visa and provide a seamless travel experience.

Note: commercial airlines will begin offering flights soon as well and a round trip from Miami to Havana will cost approximately $400 – $500 USD.


Okay, So I’m Allowed to Go! Where Should I Stay?

While Cuba offers its tourists many hotel options including the Parque Central Hotel and the iconic Hotel Nacional de Cuba, there are tons of great (and very inexpensive) Airbnb options. We stayed in our own private Airbnb apartment in Central Havana during our stay and had an amazing experience doing so.

The location was fantastic and our host who lived with his family next door was incredibly warm and helpful. He gave us recommendations of what to do, where to eat, and even made restaurant reservations for us. He also took us to a travel agency across the street to book our day trip to Viñales.

We did not have WiFi, the most comfortable beds, or quiet evenings (due both to the thin walls and the loud sounds coming from the outdated automobiles), but it was important to experience for a few days how Cubans live their entire lives.

The apartment was in Centro Habana, in the middle of the city and near the water (by the Malecón), and it was walking distance to Old Havana and many of the historical sites.

Malecón Havana Cuba travel guideWalking along the Malecon, the esplanade along the water in Havana


How Long Should I Go to Cuba For?

This depends on how much time you have for your trip and how much of Cuba you are interested in seeing. Many people don’t realize how big Cuba is. It’s the largest island in the Caribbean and is even bigger than Iceland.

I met a girl from Sweden during my trip who was spending 3 weeks in Cuba, visiting Havana, Trinidad, Cienfuegos, Santiago and more. Others fly in from Miami for a long weekend and check out Havana.

I personally went for 4 days, spending 3 in Havana and 1 in Viñales, which is a day trip you can do from Havana. I felt like a got a good feel for Cuba, but if you have more time or want to see more, there are plenty of options. There are also beach towns like Varadero if you’re interested in some beach time.


Should I Only Stay in Havana or Should I Spend Nights in Other Cities Also?

This depends on how you structure your trip. If you plan to visit Havana and do a day trip to Viñales or Varadero, you can be based out of Havana entirely. If you plan to visit cities like Trinidad that are further away, then it probably makes sense to spend at least one night there. And you could pair that with Cienfuegos, which is nearby as well. If you want to go even further east and visit Santiago, I would recommend flying (it’s a 1.5-hour flight or 15-hour bus ride), and I would definitely spend at least one night there as well.



Cash is King

American debit cards do not work in Cuban ATMs on the island, and credit card usage is practically non-existent. Make sure to bring cash to cover all of your trip expenses, which you can convert to CUCs (Cuban Convertible Pesos) at the airport when you arrive. Note the local Cuban Peso (CUP) is their second currency, used by local Cubans.

Can I Snapchat from Cuba?!

Unless you’re willing to pay a crazy $2 per 1 MB for CUBACEL roaming, leave your phone on airplane mode! Further, don’t expect WiFi either. Our Airbnb which was relatively nice did not have WiFi connectivity, though a nearby hotel offered short-term WiFi access in their lobby for a few CUCs per hour.

Also, this was my first trip with my GoPro HERO4 Silver and I absolutely loved it. I shot a lot of pictures and video with it, and am excited to use it on future trips as well.

The Weather

Cuba is a Caribbean Island and with that comes heat and rain. Late Fall through Spring are the best times to visit the country before it gets too hot and also before their rainy season in May.

Do I need a Plug Adapter?

Approximately 90% of Cuban outlets in hotels & Airbnb’s have the same U.S. outlets. Occasionally at hotels that cater more towards Europeans, it will be the circular two-pronged European plug, but the vast majority of Cuba offers the U.S. plug outlet.

Is it Safe?

Despite the economic and political challenges that the Cuban people face, they are an extremely friendly and safe community. During our time in Havana, we always felt safe, even walking on side streets late at night. However, Cuba is still a communist country so be careful and as with all traveling take standard precautions.



First Impressions

Since Cuba is a socialist country, when you get in a cab you’ll notice there are no commercial billboards anywhere. Any signs will be filled with revolutionary sayings and government propaganda. You’ll also notice the immense economic differences, the rundown buildings and the lack of infrastructure.


Havana Activities:

  • Walk around and explore Old Havana, watch the pick-up soccer games in the street, the skateboarders and the mothers sitting on the stoops with their children
  • Walk along the Malecón on the waterfront
  • Take a cab ride around the city in a convertible classic car
    • Ask to go through Old Havana
    • Fares should typically be pre-negotiated (roughly 1 CUC per KM)
  • Hop on Hop off Havana bus
    • Catch at Parque Central, 10 CUCs for the ride
  • Go to Plaza de la Revolución (Revolution Square) and the Monument to Jose Marti
  • Visit La Bodeguita de Medio
    • Ernest Hemmingway’s favorite bar in Cuba
  • Visit the historical hotels
    • Hang out in the outdoor courtyard and have a drink at the Hotel Nacional de Cuba
    • Have a drink on the rooftop of Parque Central Hotel

Additional Activities:

  • Visit Fort de San Carlos de la Cabana
    • Go for the sunset and the guards show at 8:30 p.m. followed by firing of the cannons at 9:00 p.m.
  • Local Beaches
    • Playa del Peste Beach
    • Varadero
    • Guanabo
  • Havana Club Rum Museum
    • Touristy but if you’re into rum, not a bad thing to do if raining
  • Drinks & Salsa in Plaza Vieja
    • The city square of Old Havana
  • El Capitolio
    • The capital building
ButcherA Cuban butcher preparing meat in Central Havana


Interact with the Locals

One of the highlights of our trip to Cuba was the time we spent interacting with the locals, learning about the economic and social struggles that Cubans have had to endure for decades. The average Cuban monthly income is approximately $30 to $50 USD per month and it is nearly impossible for a Cuban to leave the island for vacation or otherwise.

The Cuban people are incredibly sweet and caring and want you to enjoy your stay on their island. Get to know them and let them get to know you. It was very meaningful to engage with them on social and political issues, to better understand their frustrations and also feel gratitude for the rights we enjoy in most of the modern world.

While Cubans aren’t permitted to criticize the government openly, their frustrations are palpable. Given the limited opportunities, the Cuban people are more focused on survival than on prosperity. And while foreign trade restrictions are in the process of being loosened, confusion and frustration still remain strong. Prospective investors in Cuban enterprises have complained of the lack of transparency. The Cuban government demands to be paid in their stronger convertible peso currency, pocket the sum, and then pay Cuban employees a smaller piece of the pie in their local peso.

Since the average monthly Cuban salary is so low, Cubans try to make money via other means such as selling things on the street or acting as a “broker” for bars and restaurants. Be cognizant that they are just trying to support themselves if you are asked to follow them to a local restaurant or store.



Primarily influenced by West Africa and Spain, Cuban music is widely considered one of the richest and most beautiful styles in the world. Make sure to experience it during your trip!

While not Cuban, during our stay we also were lucky enough to enjoy a free Rolling Stones open air concert at the Ciudad Deportiva in Havana. Nearly half a million Cubans came and now U2 possibly coming as well for a free concert as well. The show was incredible as Mick Jagger rocked the crowd in front of an estimated 450,000 locals!

StonesMick Jagger rocking the crowd in Havana!

Cuban Art

For those interested in visiting art galleries, there are many fantastic options. Below are just a few of the many opportunities on the Island. There is also a plethora of beautiful street art that you will observe by walking the city.

Art Gallery Suggestions:

  • Susette Martínez
    • +53 (0)535 258 5678. Half-day art tour: CUC$40 per person. One-day art tour: CUC$60 per person. Transport is not included for the tours.
  • Museo de Bellas Artes Calle Trocadero between Calles Zulueta and Monserrate, La Habana Vieja
    • +53 7 861 0241. Tues–Sat, 9am–5pm; Sun, 10am-2pm.
  • Factoría Habana Calle O’Reilly no.308 between Calles Habana and Aguiar, La Habana Vieja
    • +53 7 86 49518. Tues-Sat, 9.30am-Sat; Sun, 9.30am-1pm.
  • Galería Habana Calle Línea no.460 between Calles E and F, Vedado
    • +53 7 832 7101. Mon-Fri, 8.30am-5pm.



Cuban Food

Cuban food often consists of meats, fish, rice, beans and local vegetables like Yucca. Paladars are very common – this traditionally referred to eating in someone’s home but now is the term for an owner-managed restaurant. Given the eased U.S. travel restrictions and subsequent rise in American tourists to Cuba of nearly 80% in 2015, an estimated 300 restaurants and bars have opened in Havana in just the past two years.

Just ten years ago when Cuba remained under the rule of Fidel Castro, those with money did not flaunt it. Now under brother Raúl Castro’s rule, Cubans are going out to nice bars and restaurants in style.

Paladar dessertFamous and incredibly delicious Fresa y chocolate dessert at Paladar La Guarida


While the restaurant and nightlife scene may be expanding, always be sure to drink only bottled water during your trip. Also in general during your stay in Cuba be careful and take all food precautions for travel to a third world country, and be careful with any local street food. Our Airbnb host recommended when choosing restaurants always pick places with many people. It’s likely the restaurant will be serving fresh food and produce given a larger turnover with more people.

Making reservations at suggested Cuba restaurants shouldn’t be too difficult. Paladar La Guarida, for example, accepts reservations via email, and otherwise, your credit card concierge service can assist. Lastly, your hotel or Airbnb host would likely be willing to assist in making a reservation for you if you ask.

2Lasagna at Paladar La Guarida

Recommended Havana Restaurants

  • El Cocinero
    • Trendy restaurant with very good food, make sure to ask for the terrace/rooftop seating, Octopus was amazing, a lot of fun, next to Fabrica de Artes, nice view from the terrace
  • Paladar La Guarida
    • Very popular Havana restaurant, very good food, service was not very good, big scene and nice bar
    • Walk up several flights of stairs, crowded scene, try the Marlin tacos and the incredible fresa & chocolate dessert
  • La California
    • Underrated, beautiful decor, extremely friendly wait staff and fair prices for delicious food
    • Try the lobster and/or the mariscos pizza
  • El Litoral
    • Located on the Malecón, this place has great local food at the right price
1aMariscos Pizza at La California

Other Restaurant Recommendations

  • Los Amigos Paladar
    • Local food recommended by Anthony Bourdain
  • Restaurante Paladar Café Laurent Habana
    • Nice rooftop
  • San Cristobal Paladar
    • Hosted President Obama during his visit to Cuba
  • Taberna Castropol
    • Nice for cigars on the terrace at sunset
  • El Chanchullero
    • Tapas and drinks in old Havana



  • Hotel Nacional de Cuba
    • Iconic hotel
  • El Floridita
    • Great drinks, snacks and live music
  • Hotel Parque Central
    • Enjoy a drink on the rooftop
  • La Bodeguita de Medio
    • Was Ernest Hemmingway’s favorite bar in Havana
  • King Bar
    • Also serves food
  • La Esencia
    • Good music and drinks
  • Espacios
    • Restaurant and lounge



Havana is Amazing! But Where Else Should I Go?

While Havana offers an incredible array of food, culture, and fun, Cuba offers many great cities beyond its famous capital. Cuba is very much a green country, known for its agriculture and tobacco farms. You can find this natural beauty, beaches and more as you explore the diverse island!


For those looking for a 1 day trip from Havana, Viñales is the best option. Many of the mountains in Viñales were shaped during the Jurassic Period (more than 150 million years ago!), and these unique landscapes include mountains with semicircles on top and caves on the inside. Our Viñales day trip also included visiting a tobacco farm, a rum factory, having a local Cuban lunch and more.

The Farming Life

The local farmers in Viñales wake up early in the morning to work the fields, finishing by 11 am and resting in their iconic rocking chairs in front of their house while smoking a cigar. Then they’ll have lunch and take a siesta in these famous Viñales rocking chairs.

The houses are very colorful, with many painted green, blue or pink. The roof tiles reflect Cuban architecture of the 18th and 19th centuries, and some roofs are still made from leaves of trees. Older houses have walls made of wood, either from palm trees or pine trees.

Rum Factory Visit

In Pinar del Rio during our Viñales trip, we visited a rum factory and tried an incredible sweet rum called Guayabita del Pinar, La Occidental, 1892 (Dulce). Their sweet rum cost only 4 CUC (approximately $4 USD) per bottle and was amazing!


Despite having very limited access to technology, Cuba continues to produce the best cigars in the world. Their ability to regulate the amount of sunlight, temperature, and humidity using traditional methods like opening and closing windows pales in comparison to the technology available to other countries today, yet Cuba still dominates the cigar game with world renowned brands such as Cohiba and Monte Cristo.

During our trip, we visited a tobacco farm and watched local Cubans hand roll cigars that we then smoked. Interestingly, 75% of the nicotine in tobacco leaves lies in the stem, which is stripped and then sent to cigarette manufacturers.

CigarsA fresh box of “Habanos” – Cuban Cigars


Mural de la Prehistoria

Just west of Viñales village is the famous Mural de la Prehistoria. Painted in the early 1960s by Leovigildo González Morillo, this beautiful mural represents the evolution from dinosaurs to humans today. The mural is 120 meters long by 80 meters high!

2016-03-26 12.49.10

Other Cities to Visit

Other popular cities to visit include Cienfuegos, Trinidad, and Varadero. Santiago is another option for those interested in learning more about Cuba’s history. A lot of music comes from here, and Santiago is where the revolution started.


If possible, please bring what you can for the local Cubans. Even little things like toothpaste, toilet paper, USB drives, clothes go a long way for the underprivileged locals, and it will be well received.  For example, our Airbnb host could not buy sheets to run his apartment and he also could not buy a coffee maker. Ask your Airbnb host in advance, they will be very grateful for anything you could bring.


Cuba is a beautiful island that offers an incredible combination of food, art, and distinct culture. The Cuban people are warm, filled with soul and have demonstrated extreme resilience in the face of communism. In 2018 it is expected that the 84-year-old Raúl Castro will step down and give power to the current Vice President Miguel Díaz-Canel, who is almost 30 years younger. We hope that the restoration of relations with the United States coupled with a transition to new leadership will bring the Cuban people the economic empowerment and political freedoms that they deserve.

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