How to Travel to Cuba, By Plane, Vacation or Cruise

Jul 20, 2015

In the past year, diplomatic relations between the U.S. and Cuba have softened considerably. The U.S. government loosened travel restrictions that have been in place for 54 years in December 2014 and we’re seeing more and more travel companies beginning to offer mainstream trips. Tourism has surged 15% since last year according to a July 13, 2015, report from Bloomberg Business, who attributes much of the surge to American tourists trying to beat the crowds.

American travelers still can’t just up and go to Cuba for a beach vacation of umbrella drinks and all-inclusive buffets -- like they can for the Bahamas, Jamaica or Dominican Republic -- but don’t be surprised if that day comes in the future. After all, Cuba is one of the most popular leisure destinations in the Caribbean for Canadian and European travelers.

For now, these are the companies that offer direct travel into Cuba from the U.S.


  • JetBlue: Started offering charter service from JFK and MIA, booked through Cuba Travel, in July 2015. Flights can only be booked here at These chartered flights arrive and depart every Friday.
  • American Airlines: A company called ABC Charters uses AA planes from Miami and Tampa to fly to Havana, Cienfuegos and Santiago de Cuba.
  • Sun Country: Some nonstop flights from Miami and New York (JFK) are available via charter aboard Sun Country.
  • Another option is to fly through a third country, such as Canada, Mexico or a nearby Caribbean island like the Bahamas. The two legs must be booked separately.

Note: Travelers booking their own itinerary should book hotels far in advance as they fill up quickly.

Vacation Packagers

The benefit of traveling with a packager is that they do all the paperwork. From the visa to medical insurance and ensuring all regulations are met, they’ve done this before and the cost is usually included in the package price.

  • smarTours: The SmarTours itinerary operates under the people-to-people visa and includes 10 nights spread out across four Cuban towns and cities. Visit the major draws like Havana and Cienfuegos and go off the beaten path to Camaguey, a UNESCO World Heritage Site, and Holguin, where Christopher Colombus landed in 1492. Our Deal Experts love the cigar factory visit and the chance to ride in vintage automobiles through Havana.
  • Discovery Tours by Gate 1: The small-group arm of Gate 1 Travel, Discovery Tours organizes group tours with a maximum of 22 travelers using the people-to-people visa. This expert tour operator has been exploring Cuba with travelers for more than a decade, so they’ve got a head start on finding the best places and things to see. Cooking lessons, live jazz, and a tour of Trinidad top our favorite experiences on this trip.
  • Friendly Planet: Under the people-to-people visa, Friendly Planet offers three different itineraries for travelers to choose from. A five night trip offers an introductory tour of Havana and afternoon trips to Hemingway’s home, the Alamar housing district and Las Terrazas farming community. The six-night trip splits travelers time between Havana and slows down with a beachside stay in Varadero. An in-depth, eight-night trip is perfect for travelers who want to travel at a quick pace and visit dozens of destinations from small towns to the beach and bustling cities.
  • Apple Vacations: Caribbean and Mexico travel experts, Apple Vacations is the most recent to throw their hat in Cuba’s ring. Starting in the fall, travelers can book a people-to-people tour through the packager. Although details are sparse at the moment, the company has promised shorter tours that are cost accessible as well.
  • Cultural Contrast: Cultural Contrast has been taking travelers to Cuba for 25 years and specializes in trips outside of the typical people-to-people tours of other packagers. All fully licensed and authorized trips, Cultural Contrast has broad itineraries, ranging from chef-led culinary tours to yoga retreats and visits to run the Havana Marathon.
  • Globus Journeys: With three varied itineraries, Globus Journeys offers people-to-people tours that plot unique courses through Cuba. Opt for one of the shorter, eight-night trips that focus either on Havana and the colonial beach towns or skip Havana and explore Eastern Cuba -- an area few other tours visit. The third itinerary is easily the most extensive we’ve seen, with 16 nights spent traversing Cuba from coast to coast, leaving no highlight behind.


  • Carnival: Beginning in May 2016, Carnival will operate people-to-people cruises setting sail from Miami. The itinerary is yet-to-be-announced, but trips are available to book. Prices include all on-board and on-the-ground social and cultural immersion activities.
  • MSC  Cruises: Cruise operator MSC will be the first to set sail for Cuba, starting this December. These cruises offer just a taste of Cuba in addition to other Caribbean destinations like Jamaica and Cayman. Spend two and a half days in the port of Havana, letting travelers explore the city at their own pace.
  • Group IST: For those who want a more intimate experience than a full blown cruise, sail aboard a mega-yacht from Havana to Cienfuegos on a people to people visa. The ship features oceanview cabins and stops daily with tours in Havana, Guanahacabibes National Park, Cayo Largo, Trinidad and Cienfuegos.

Tips for traveling

U.S. travelers going to Cuba need to know a few things to keep the trip worry-free.

  • If possible, bring cash in the form of euros or Canadian dollars to change over to Cuban currency.
  • Credit cards aren’t widely used, and changing U.S. currency incurs an additional 10% penalty.
  • Under the new rules, Americans can bring back up to $400 in goods for personal use, but no more than $100 in total of alcohol or tobacco products.
  • Don't expect easy access to Wi-Fi or even wired Internet. Do your research on where, or even if, you can plug in before you leave home.
  • To follow U.S. State Department rules, trips that fall into one of the 12 categories (ranging from education to research to humanitarian efforts) no longer require a specific license and can be booked. But all travelers still require a tourist visa and medical insurance. Often, the visa cost is covered by the charter airfare or the tour operator.
    • Visiting family
    • Official business of the U.S. government, foreign governments and some intergovernmental organizations
    • Reporting trips by journalists
    • 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 authorized export transactions

The additional restrictions and documentation means Cuba is a more expensive island vacation than other Caribbean hot spots, but for travelers wanting the “authentic” Cuba experience, now is the time to go.

All facts were confirmed and accurate as of July 20, 2015.

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