How to Travel to Cuba: Tips from the Experts!

How to travel to Cuba this year - ochristine

As if Americans weren't already stoked after learning we can now visit Cuba (legally), long-awaited direct flights to Havana have U.S. travelers jumping over furniture in wanderlust anticipation. 

Interested in making your way down to Havana's quaint streets lined with old cars, the best Ballet in the world, beautiful surrounding towns, and vibrant culture? I've consulted with expert travel bloggers to bring you a list of amazing things you can't miss and everything you need to know in preparation for your trip to Cuba.


  • 8 Facts to Know Before Traveling in Cuba

  • Things to Do in Havana, Cuba

  • Outdoor Activities in Cuba

  • Amazing Adventures in Viñales, Cuba

  • How to Visit Cuba for the International Cuban Ballet Festival

  • How Americans Can Visit Cuba

8 Things to Know Before Your Trip to Cuba

The Sophisticated Life gives the scoop: Throw any preconceived notions about Cuba out of the window as you prep for your time there. Nadeen from The Sophisticated Life has prepared an in-depth list of 39 interesting, unique, and random things she learned about visiting Cuba. Here are 8 of my favorites:

A photo posted by Nadeen. (@thesophislife) on

  1. A popular mode of transportation all around the island is a “Spider”. It has a horse with 4 legs and a cart with 4 legs: 8 legs like a spider.

  2. Hitchhiking is a way of life. You will notice hitchhikers in the middle of nowhere-even women with babies.

  3. Due to the irrigation system in Cuba, it is recommended that you do not flush the toilet paper.

  4. Chewing gum is a hot commodity! Bring a few packs for your guides and hosts.

  5. There is universal free healthcare. I will say that again. There is universal FREE healthcare.

  6. Many Cubans have more than 1 job. You can make more money as a taxi driver than as a doctor.

  7. There is the John Lennon public park with his statue in Vedado Havana. The Beatles were banned in Cuba in the 1960s and 1970s so people would gather in this park to sing their songs in secrecy.

  8. There is a 5th Avenue in the Miramar area of Havana. Just like NYC, it is a very upscale area. Many embassies and mansions of former residents that fled during the revolution are located here.

For more facts and a 7-day guide to exploring Cuba, visit The Sophisticated Life blog.

What to Do in Havana, Cuba

The Travel Sisters Explore Havana: The Travel Sisters blog visited Cuba in 2012 on a people to people tour, and though it was a few years ago their tips and favorite activities are still totally relevant. Their favorite city in Cuba was Havana, and they returned packed with suggestions including the following:

  • For amazing panoramic views of Havana, dine or have drinks at La Torre located on the 33rd floor of Havana's tallest building.

  • A great cultural activity is to watch ballet at the beautiful and historical Gran Teatro de la Habana.

  • Drink at Bodeguita Del Medio. Around the corner from Cathedral Square is Bodeguita Del Medio which is a legendary bar made famous by Ernest Hemmingway and its mojitos.

Two important things to know:

  1. "Bring toilet paper and small change for tips with you. Some bathrooms had no toilet paper and some had an attendant handing out toilet paper (you are expected to leave a small tip or pay a small fee). 

  2. Also, Internet in Cuba is pricey and hard to find. There was no free wi-fi or internet anywhere. We had to pay for internet (usually 6CUC an hour - $6 USD) but sometimes they would run out of access cards at the hotel."

Read more about The Travel Sisters' experience in Havana on their blog.

Outdoor Activities in Cuba

My Adventures Across the World Loves Hiking in Cuba: Claudia from My Adventures Across the World is obsessed with Latin American travel and the perfect go-to expert for in depth travel guides. When asked about her Cuban suggestions, she gave some insightful tips:

"Pick fewer places, and actually enjoy them properly - or else risk spending most of the time sitting in a bus or taxi and completely blowing the budget on transportation.

"This is a safe country to travel alone, as a single woman, or even with children. Criminality rates are low, save for the occasional theft of clothes and money from suitcases locked and left inside the room: I always counted my money and my items and wrote it down on my notebook. This way, in case I realised that something was missing, I could threaten to call the police: just threatening to do it made it magically reappear."

One recommended activity in Cuba?

  • Besides finding relaxation at the Bahia de Cochinos (see photo above), Hiking El Yunque (the flat top mountain near Baracoa) in the Guantanamo region is a must-do.

"A guide is required as the vegetation is quite thick and it is easy to get lost: there are rivers to cross (either walking in the water, or catching a boat if it is available), a jungle to walk through and due to the regular rain that falls in the region, the terrain is very muddy and slippery (especially on the way down).

The hike is quite strenuous due to the high humidity levels and the heat, but the landscape and the views make it totally worth it!"

Claudia's extra travel tips:

  • Go between November and March, when temperatures are not as hot and it rains less.

  • The tastiest food in Cuba is in Baracoa: eating shrimps, octopus and lobster in coconut sauce is what to do in Cuba!

Read more about Claudia's adventures in Cuba on her blog.

Amazing Adventures in Viñales, Cuba

See Her Travel Goes to Viñales, Cuba: Emily from See Her Travel has explored different parts of Cuba and shares great information about her journey. Watch the video above for a sneak peek! 

A photo posted by Emily (@seehertravelemily) on

"Vinales, Cuba is located on the Western end of the island, about 5 hours from Havana by bus. A small town, it is nestled in the Vinales Valley, made by hundreds of mogotes, unique rocks that tower above, making caves, cliffs, and all kinds of pockets to explore. Vinales has become a top site for tourism in Cuba, but remains a naturally gorgeous and peaceful place to spend a few days!"

Read more on the See Her Travel blog for tons of articles on Cuba.


How to Visit Cuba for the International Cuban Ballet Festival

Some of the best ways to get to Cuba, as you can tell, is with a cultural tour (people to people / art tours). The award-winning Sarasota Cuban Ballet School in Sarasota, Florida offers yearly trips to the International Cuban Ballet Festival.

This all-inclusive eight-day experience (including leaving from Tampa) offers a local exploration of Havana, access to the National Cuban Ballet School (the largest in the world), tickets to six ballet performances, museums, and more.

Visit the Sarasota Cuban Ballet School's website for more information on how you can join them in Cuba for the International Cuban Ballet Festival. What better way to experience the country than with authentic Cuban Ballet, friendly locals, and a robust art scene?

How Americans can visit Cuba

Divergent Travelers Gives A Full Run Down On Visiting Cuba For Americans: Now that you have the inside scoop on what to see, eat, and do, here are the must-know logistics for your trip to Cuba from Lina and David from Divergent Travelers. 

  • Generally, any American traveling to Cuba under a General License should plan on keeping detailed records of their time in Cuba and how it pertained to the license you claimed. In short, don’t claim that you are visiting for religious reasons and then book in a week at an all-inclusive resort in Varadero.

  • Cuban Visa for Americans: To save money, fly with a connection.

"Had we decided to fly on the direct charter from Miami to Havana, we would have had to obtain a Cuban Visa from a US based Cuban travel agency, to the tune of $85 per person. By traveling through a foreign gateway city, we were able to purchase our Cuban Tourist Visa from the gate counter before boarding our flight to Havana. The cost was $20USD per person, a significant savings from trying to obtain the visa in the USA."

Other tips from them:

  • Check bus prices before agreeing to book a ride with a taxi collectivo on long haul journeys

  • When visiting Havana, be sure to wander outside of Havana Viejo into the Centro area to see how Cubans live for a more authentic experience. Get up close with them, interact with them and enjoy the real Cuba this way.

Visit the Divergent Travelers travel blog for the full (up to date) scoop on the legalities of visiting Cuba.

Official Reasons You Can Use to Fly to Cuba (according to JetBlue):

Lastly, if you are feeling good about your trip, make sure you have proof of a return ticket and use one of these officially approved reasons for travel to avoid any issues:

  • Family visits

  • Official business of the U.S. government, foreign governments, and certain intergovernmental organizations

  • Journalistic activity

  • Professional research and professional meetings

  • Educational activities

  • Religious activities

  • Public performances, clinics, workshops, athletic and other competitions, and exhibitions

  • Support for the Cuban people

  • Humanitarian projects

  • Activities of private foundations or research or educational institutes

  • Exportation, importation, or transmission of information or information materials

  • Certain export transactions that may be considered for authorization under existing regulations and guidelines


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Are you ready to visit Cuba?

I hope you feel better prepared to plan your trip to Cuba. There is so much to do and see, and plenty of experts to help you get it done - legally! Share this article with your friends and help them get excited, too!