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Cuba Tours

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20th Anniversary Celebration Tour - 5 nights / 4 days - Havana
 This tour is closed. We will not be resuming travel to Cuba this year. We are working closely with our Cuban partners and are hopeful to return to the island as early as possible in 2022. Click here to be notified when 2022 departures become available!
Map 20th Anniversary Tour

It’s amazing to think that it's been 20 years since insightCuba sent the first group of Americans legally to Cuba. In 2000, we were told it couldn’t be done. Since then, we’ve created hundreds of thousands of experiences for U.S. travelers wanting to see this incredible destination for the first time.

Join us for a 20th Anniversary Celebration tour to Cuba this November and experience what we love most about this incredible destination. Experience our favorite places, hear the stories, and meet some of our best friends who for 20 years have brought Cuba to life, and made it all possible.   

A trip worthy of happening once in 20 years. Join us and Discover Cuba Through Its People, like never before.  


Day 1
Day 2
Day 3
Day 4

Each departure is custom-curated to provide the best experiences possible and from time-to-time specific experiences, and/or restaurants may not be available and will be replaced by an item of equal or greater value. A final list of daily experiences and dining options is provided roughly two weeks prior to departure. Each tour provides a full-time schedule of Support for the Cuban People activities and is fully compliant with U.S. Department of Treasury, Office of Foreign Assets Control regulations regarding travel to Cuba. 

  • Four nights at the Meliá Cohiba Hotel in Havana

  • Cuban visa

  • 20th Anniversary Celebration Gala

  • Expert Cuban guide and private driver

  • Transportation and airport transfers

  • Exclusive-guided visits and experiences

  • Four breakfasts, three lunches, and three dinners

  • Gratuities for luggage handling and restaurants*

  • Certification of travel to Cuba under the U.S. Department of the Treasury general license

  • 24 hour on-tour customer service


  • Flights
  • Room & suite upgrades


Health insurance in Cuba, included in the cost of your airfare 

Customary end-of-tour gratuities for the Cuban guide and driver are left to the guest’s discretion and should be based on your satisfaction with the level of service received.



Dwell on views of city and sea at the elegant Meliá Cohiba, a five-star hotel on Havana’s famous Malecón. With its envied location in the affluent Vedado neighborhood, guests are steps away from Cuban life, including rum tasting, live music, and evening salsa at the hotel’s Habana Café.

This tour is currently suspended. But we're working on new departures and a new, enhanced itinerary, so stay tuned!
20th Anniversary Tour

This tour does not include flights, but our flight specialists are happy to help arrange them! When you book, tell us which city you're coming from, and we'll get back to you with a quote and a proposed flight schedule within 5 business days. If you accept our quote, we'll add the price to your balance due. You're also welcome to book your own flights.

Please note that presently, only a few airlines are operating flights from the U.S. to Cuba, including American Airlines, JetBlue, and Southwest. For the most current information and schedules, please contact us or the carriers.