Top Cuba Travel Companies for Americans

These travel agencies can get Americans to Cuba legally

For the first time since the 1950s, Americans are allowed to travel legally to Cuba, but it's still not a simple process if you want to book a flight and hotel in Havana or Varadero, for both bureaucratic and supply related reasons. That's why most Americans still book tours through companies that have won special approval from the U.S. State Department to run cultural-exchange trips to Cuba.

Going on a group tour means you're guaranteed not to run afoul of the still-sticky rules governing Cuba travel, which require that your trip focuses on cultural exchanges, not tourism (in other words, you should be meeting Cuban people and learning about their culture, not lying on the beach all day). Each of these companies has crafted tours full of cultural experiences that you'd be unlikely to arrange all on your own. Plus, you'll be traveling with companies that have had years of experience operating in Cuba and with guides who are intimately familiar with this fascinating...MORE country and its people.

Note that all Cuba tours are fully escorted, include all lodging and meals, and have a mandatory overnight in Miami for pre-trip trip orientation.

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  • 01 of 10
    Havana skyline
    ••• M G Therin Weise/Photographer's Choice RF/Getty Images

    One of the first tour companies to win approval for people-to-people tours, Insight Cuba is based in New Rochelle, N.Y., and has been bringing Americans to Cuba since 2000. Their tour schedule is especially diverse, with programs focused on music, baseball, and the Havana Marathon as well as tours that get visitors outside Havana to explore the still mostly undiscovered countryside. Their 4-day Weekend in Havana tour is a rare opportunity for a quick Cuban getaway.

  • 02 of 10
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    ••• Street music in Cuba. © VXLA/CC by 2.0

     Canadians have been traveling to Cuba legally for decades -- experience that benefits this British Columbia based agency that also is licensed to bring U.S. citizens to Cuba. Programs include basic introductory tours, an Arts and Culture Tour to Havana, Trinidad and Cienfuegos, and a trip to the annual Havana International Jazz Festival.

  • 03 of 10
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    ••• The El Floridita bar in Havana, a famous Hemingway hideout. © Momo/CC by 2.0

    Classic Journeys operates tours all over the world and has added Cuba to its offerings. Programs include a seven-night walking tour, a family oriented program designed with children and teens in mind, and a Havana weekend tour that includes stops at Ernest Hemingway's house, salsa lessons, and a stay in Old Havana.

  • 04 of 10
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    ••• Carriage in Varadero, Cuba. © Harry Pehkonen/CC BY 2.0

    In addition to the typical Havana and Cuba introductory tours, Friendly Planet offers an itinerary that includes a stop in Varadero, the beach destination most visited by non-U.S. travelers.

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  • 05 of 10
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    ••• Birds in the wetlands of the Zapata Peninsula. © Javier Ignacio Acuna Ditzel/CC by 2.0

    This ecotourism company specializing in nature travel offers two Cuba tours: one focused on Havana and the city of Trinidad and a longer journey that includes visits to the wetlands of the Zapata Peninsula, a boat trip through limestone caves off the coat of Vinales, and a stop at a farm that raises tobacco for Cuba's famous cigars.

  • 06 of 10
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    ••• Cuban cigar maker. © Les Haines/CC by 2.0

    International travel company offers a single 8-night Cuba itinerary that includes stops in Old Havana, the historic towns of Santa Clara and Remedios, a tobacco farm, and the usual cultural, musical and artistic performances and visits required under the "people to people" travel rules.

  • 07 of 10
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    ••• Cuban salsa dancers. © Locally Sourced Cuba Tours/CC by 2.0

    Another legal Cuba travel pioneer, Central Holidays offers a 7-night "Havana: Then and Now" tour and a 9-day program that takes in Havana and the less-traveled historic cities of Camaguey, Trinidad, and Cienfuegos. 

  • 08 of 10
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    ••• The colonial Plaza Vieja in Havana, Cuba. © Thomas Munter/CC by 2.0

    Offers four Cuba tours with some interesting twists, including programs focusing on the island's Spanish colonial history, Afro Cuban culture and music, and a rare chance to visit the east coast towns of Guantanamo and Baracoa.

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  • 09 of 10
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    ••• Che Guevara statue in Santa Clara, Cuba. © Marika Bortolami/CC by 2.0

    Cuba is for seniors, too! ElderTrek's comprehensive, 13-day tour of Cuba takes in Havana, the Sierra del Rosario Biosphere Reserve, Cienfuegos, Trinidad, the history of the Cuban revolution in Santa Clara, Afro Cuban music, and more.

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    ••• Trinidad, Cuba. © Stephen Colebourne/CC by 2.0

    New England based Collette Tours, one of the nation's biggest tour companies, runs a Rediscover Cuba tour several times a year; the itinerary includes visits to Havana and Trinidad, a steam train ride to a sugar plantation, a choral concert, and more.