How to Travel to Cuba in 2018 – 4 Ways to Enjoy the Once Forbidden Island NOW



Let’s cut to the chase about U.S. travel to Cuba.

Why Travel to Cuba?

NOW is a very special time in Cuba’s history. It’s a unique place where the past and present coexist. The classic cars, colonial architecture, and tobacco farms somehow combine with the new wave of private businesses, some technology, and a thriving art scene beyond your imagination. It’s as if Cuba is evolving to its Cuba 2.0.

You Must Experience Cuba for Yourself.

All the pictures, documentaries, and paparazzi don’t do this culture justice. The essence of Cuba has to be felt through its music, food, rum libations, and most importantly its people. There is a genuine happiness to everyone you meet. Cubans are welcoming and very genuine, even to Americans. Cubans understand that our governments don’t get along. They don’t hold that against Americans that travel to Cuba. They believe that we are neighbors with similar interests: baseball, music, movies, fashion, and more. You may want to read more about this in my travelogue Cubicle to Cuba. Cubicle to Cuba is available in Spanish. Sí sí en español.(Updated June 2018)

Debunk the Myth about the U.S. Embargo

Many think that during the Obama administration that the U.S. Embargo was lifted. That is a big myth. The U.S. Embargo is still in place, which limits financial transactions with the Caribbean island, including travel for tourism sake to the island. Obama’s administration loosened the restrictions on American travel to Cuba, including commercials flights, cruises, and even independent travel. However, with the current Trump administration, some of those restrictions have been put back in place. To read about the Trump changes go to last year’s Cuba travel article.

Four Ways You Can Travel to Cuba NOW


What is Legal Travel to Cuba?

The short, but vague answer is that as an American traveler, you must fall under one of these twelve categories of travel to Cuba.

Ways You Can Legally Travel to Cuba

Havana_Cuba_Capitol_Building_and_Classic_CarsU.S. Licensed Travel Agency or Tour Operator for Cuba Holidays

  • You can go with a U.S. licensed tour operator on a group tour. Over the past six years, I have worked for various companies leading people-to-people educational tours in this manner. I’ve logged more than 30 trips, written numerous featured articles, and even published a book, Cubicle to Cuba. These groups are typically 20 or fewer individuals. Prices vary by trip duration and season. On average for 8-days the cost is $3,500-$4,000 per person. However, you typically need to fit into a pre-selected time slot. See the tours that I recommend by clicking here. If you have your own timeline, see the more customized travel below.


Old_Havana_Cuba_Skyline_from_FortCruises to Cuba

  • Cruises are another alternative for legal travel. On most cruises, you spend two days with an overnight in Havana. This is the more economical option (4-day cruise from Florida for $800-$2,500 depending on your cabin). Check out the 2018-2019 cruises to Cuba that I will be on as a guest lecturer on the Carnival Paradise out of Tampa 2018-19 and Carnival Sensation out of Miami in 2019.


Cuban_Street_Art_Havana_Cuba_2018Customized People-to-People Tours 

  • This option piggybacks on the first bullet point but allows for smaller group tours, catered to your timeline and interests. This is perfect for those that want more independent travel and a customized experience.  Contact me and I’ll connect you with the right agency, Havana tours, accommodations, and people.
  • The prices vary on length of tour, accommodations, and season. My favorite tours are 7 days/6 nights in Havana, Trinidad, Santa Clara, and Cienfuegos ($2,625 land only) or 4 days/3 nights in Havana ($1,175 land only). These tours include accommodations in bed and breakfasts or four-star hotels, private transportation, airport transfers, meals, people-to-people activities, porterage.  Contact me with when you, your friends, and/or family want to go! 

Author_Heidi_Siefkas_of_Cubicle_to_Cuba_walking_in-Old_Havana_CubaCuba on Your Own – Independent Travel to Cuba

  • As of June 2017, you are not permitted to go independently to Cuba under the people-to-people educational category. Many went this way during the Obama administration. They purchased commercial flights, obtained a visa, and filed under the independent people-to-people educational category. For years prior to all of these changes and even today, others have decided to go through third countries, but this too is illegal from the standpoint of the U.S. government. (Updated: November 8, 2017 Washington Post article on White House’s new Cuba policy.)
  • HOWEVER, new Trump-era rules allow individuals to visit Cuba in “support for the Cuban people”-one of the 12 categories of travel that require no special authorization. See how to do this below.


Best Travel Tips for Legal, Independent Travel to Cuba

If you would like to go to Cuba independently, but within the legal parameters, I suggest the following:

  • Contact me with your dates, interests, and how many people.


  • I’ll connect you with my trusted partner for guides, accommodation, and transport in Cuba. This will make things a breeze as transportation is tricky in Cuba, accommodations need to be centrally located, and a guide will be able to enhance your trip whether just for a day or two, while allowing plenty of on your own time.


  • Investigate & purchase your own airfare. I like JetBlue as well as American Airlines.


  • Check which of the 12 categories you are legally traveling under (Many choose to check support of the Cuban people – See this article in the Wall Street Journal)


  • Buy your visa for Cuba at the airport ($50-100 depending on airline)




NOW is the Time to Experience Cuba.

Find Out More from My Many Cuba Travel Articles:

If you still have Cuba travel questions, contact me!

As always, here’s to looking up!


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