Travel to Cuba Legally with Cultural Island Travel

Cultural Island Travel-Custom Group Tours

We take pride in creating the best possible custom group travel experience for you and your group. It’s no coincidence that we have received accolades from many clients for our dedication, attention to detail, traveler experience and service. We truly enjoy crafting custom itineraries based on your needs and our experience with Cuban culture and music for the past 18 years. We have no minimum number of passengers on our tours. We are also able to arrange hotels, villas, mansions and apartments depending on group size. We make every effort to work within your budget. We have taken famous actors and performers to Cuba while ensuring their privacy. We also specialize in luxury trips, film shoots, concert productions, VIP travel, Private Flights, Cigar trips, authentic Photography trips, Cooking Classes and Food Oriented Trips, Family Reunions, Bachelor and Bachelorette parties. Call us today to discuss at 1-800-494-1945.

Travel and Fundraise?

Many associations/organizations use their trip to raise awareness—or even funds—for their work. This is beneficial on many levels. Your organization generates funding and provides a great member benefit, we get to help you achieve your goals, and everybody has an experience of a lifetime in Cuba.

It’s all about you!

Our main focus at Cultural Island Travel is: you. We want you and your group to have an authentic and unforgettable Cuban experience. Relax, and let us do all the work for you. Tell us what your group’s schedule, needs, and interests are, and leave the details and all the reservations to us.

Our trips are fully Legal

As our guest, you’re authorized to travel to Cuba under our people-to-people license issued by the U.S. Department of the Treasury. What this means for you: No lengthy applications, no need to hire expensive lawyers, no worries.

We Can Work With Your Affinity Group

We have done work with the following groups including, but not limited to:

  • Actors and Performers
  • Movie Directors
  • Magazine Editors
  • Families
  • Museums
  • Universities
  • Alumni Associations
  • Dance groups
  • Travel Clubs
  • Cigar Aficionados
  • Art Associations
  • Music Aficionados
  • Architecture Societies
  • Music, Dance or Art Venues
  • Religious groups and choirs

Let the Experts Plan Your Trip

A group of Cuban travel experts who have lead several group tours throughout Cuba know how to create a trip you and your group will talk about for a lifetime! We contact our local Cuban partners to arrange every detail for you, including flights, hotels, people-to-people activities, and more—all custom designed for your group’s interests.

Dedicated Customer Service

Our support staff and team members are with you every step of the way, from the time you contact us, until the time you come home from your trip. We want to give you the peace of mind to concentrate on the unique experience of Cuba, while we take care of the rest.

What Now?

Have more questions or concerns? Want to book your trip now? Call to speak with our Custom Group Travel Team at 1-800-494-1945. E-mail more your thing? Please contact us at

    What Customers Have to Say

    Cynthia Johnson, CenterPoint Properties, June 8, 2018

    Cultural Island Travel did an outstanding job leading our group of 55 corporate executives through a day tour of Havana, Cuba! Each guide was friendly, welcoming and willing to help us with whatever we asked of them. CIT had our day perfectly planned. We started the trip taking two private jets from Fort Lauderdale to Havana, escorted by a very experienced CIT guide. Once we landed, three additional CIT guides greeted us on the ground and helped us get through customs. The team took our group for a drive on two motor coaches through the major squares in the city, highlighting historic monuments and detailing Cuban culture along the way. They brought us to La Corona Cigar Factory for a private tour and set up a private rum and cigar pairing at Gran Teatro de La Habana. It was a first-class experience! Even during a torrential downpour, CIT helped us navigate our way to two of Ernest Hemingway’s favorite bars where mojitos and daiquiris were waiting for us: El Floridita and La Bodeguita del Medio. CIT also arranged for our entire group to enjoy delicious meals together at two paladars: Al Carbon and La Guarida. Our executives will never forget this trip. We are so glad we trusted Cultural Island Travel to get the job done – and we would do it again!

    Caroline Hannah, January 2018

    Kristen, It was amazing. We plan to go back and go directly through y’all next time. Fernando was so kind and waited the 90 minutes it took us to disembark. I don’t know if our salsa instructor was selected by y’all, but he was a hoot. Best tour off a cruise ship ever! 

    What’s Included

    Custom tours have different inclusions based on our client’s preferences. Please see below for standard inclusions.
    • All meals listed on the itinerary
    • Pre-Departure document covers everything you need to know for a safe and enjoyable trip prior to arriving in Cuba. Upon arrival, a short orientation will acclimate you further.
    • All documents needed for legal travel authorization from the United States Treasury Department
    • All document processing including visas
    • Superior accommodations in Havana
    • Expert tour leader
    • Air conditioned modern vehicle
    • All ground transportation for tours and airport transfers in Cuba
    • All activities and entrance fees to all activities listed on your legal itinerary
    • In-country Cuban medical insurance
    • Concierge service for dinner reservations and shows/nightlife
    • Cuban Visa

    Not Included:

    • Note: Flight Costs Round Trip from varied international departure points to Havana (not included in package price) Approximately $199-499 (depending on departure airport, airline/charter vs. commercial)
    • Tips for tour leaders, local guides, wait staff, and chambermaids
    • Luggage check in costs-please check with your particular airline for allowances

    Single Supplement: Varies depending on accommodations. If you do not see what you are looking for on this tour or any of our other scheduled tours please contact us for a custom tour quote.

    Tour Dates & Prices

    Please contact us for custom rates for your preferred dates. We can offer tours anytime during the year.

    Brochure & Top Cuba Tips

    Download our Cuba Tour Brochure and Top 10 Cuba Tips to get a better idea of what to expect when traveling to Cuba on an authentic CIT tour!


      Experience Cuba With Us

      6 Day Tour

      A Taste of Cuba Culinary Tour


      Custom Tours of Cuba, Sicily, Mexico & Ireland

      7 Day Tour

      Cuban Music & Art Tour

      5 Day Tour

      City and Countryside-Havana & the famed Cuban Tobacco Fields

      6 Day Tour

      Blue Note Tour: Cuba With Award Winning Pianist Jorge Luis Pacheco

      6 Day Tour

      International Havana Jazz Festival Tour

      4 Day Tour

      Havana Weekend

      4 Day Tour

      Jet Set Havana Getaway

      4 Day Tour

      Havana Marathon

      7 Day Tour

      Ireland: Discover the Emerald Isle with Ebony!

      7 Day Tour

      Discover Mexico City & San Miguel De Allende

      7 Day Tour

      Magical Mexico City & Puebla Tour

      8 Day Tour

      The White Lotus Sicily Locations Tour

      7 Day Tour

      Taste of Sicily-Culinary Tour

      Call us today for legal travel & $200 OFF our packages booked by May 15th Departures weekly through 2025!
      Hello. Add your message here.