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20th Anniversary Celebration Tour - 5 nights / 4 days - Havana


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


Trip cancellation insurance | Airfare | Room and suite upgrades





*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.

DateDouble Occupancy
(per person)
Single Occupancy
Nov 10 – Nov 14, 2021$2,795$3,040  

GROUP RATES: 5% off land for groups of 5 - 9 guests, and 10% off land for groups of 10 or more guests booked on an already scheduled Small Group tour listed above (not inclusive of private or custom-made tours). Not combinable with any other offer. Will be applied at final payment.

20th Anniversary Tour

Once you have booked your tour, our flight concierge will gladly assist you with all your flight needs from the U.S. to Havana. Call us at 914-380-8303 for an air quote.