Why Book with Cultural Island Travel?

Your time is valuable—our Cuba Travel Experts understand this. That’s why we handle every detail of your Corporate Travel to Cuba, making sure you receive the best rates for airfare, lodging, tours, guides, and transportation.

Our service goes beyond just booking your trip to Cuba. We can arrange sightseeing, make dinner reservations, and organize a variety of excursions. Whether it’s two people or a hundred people traveling, we handle all the details to ensure a seamless trip from start to finish.

With decades of experience in running trips to Cuba, we have the expertise to make group travel a success. We can help design a day trip or plan a week long stay in Cuba. We can negotiate group/incentive airfare/ private aircraft for any size group, coordinate ground transportation, book room blocks at special rates at high end hotels, help arrange meeting and banquet space, provide meal options, organize leisure activities, sightseeing and events like cigar and rum tastings, convertible classic car rides and more!

“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!”

-Cynthia Johnson, CenterPoint Properties


Inclusive Group, Meeting & Incentive Travel to Cuba

Corporate Travel To Cuba

Decades of Experience
in Cuba Travel

We have taken thousands of clients to Cuba. From individual travelers to corporate incentive groups and VIP clients, we can make sure your clients have a seamless experience in Cuba.

Full Service for Your

We take care of full tours, lodging, all legal paperwork and have a concierge for any dinner and show reservations

Private Plane Charters & Celebrity Travel

We have worked with Questlove, Josh Klinghoffer of the Red Hot Chili Peppers, the Rolling Stones, Hollywood directors and producers. We can also help arrange private flights for your company.

Any Size Group &
Custom Tours Available

We have no minimum or maximum number of clients and can fully customize any tour.

Choose From Our Many Different Tours to Cuba

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


Frequently Asked Questions

Is it legal to Travel to Cuba?

Cultural Island Travel is licensed by the United States Treasury’s Office of Foreign Assets Control (OFAC) to conduct Support for the Cuban people travel to Cuba. We custom design itineraries that are fully compliant with OFAC guidelines such as music and dance performances, artist visits and other activities that fall under the cultural travel guidelines. These tours are open to all Americans and no application process is necessary. We are currently authorized to take any American to Cuba under the general license and our OFAC approved itineraries make sure that your travel is fully legal. Support for the Cuban people travel means you will have the chance to meet the local people of Cuba and experience their culture in depth. Cubans are very friendly and passionate and the memories of these interactions make a lasting impression on even the most seasoned travelers.

Booking a flight to Cuba? Make sure you’re booking legally! Restrictions still apply.

Have you booked a flight to Cuba recently? You may want to check the fine print. Travelers going to Cuba from the US still need to fall under one of the 12 legal categories for Cuba travel. The most popular option is “Support for the Cuban people” travel, which means you need to fulfill a full itinerary of cultural activities every day. If you sign up with CIT or another agency you will automatically quality for a visa, and we will send you a certificate of travel to Cuba ensuring ease of re-entry into the US.

Is travel insurance available for Cuba?

Cuban travel health insurance and is always included. We do strongly advise that our guests also purchase trip cancellation coverage. We partner with Travel Guard for our insurance supplier or you can choose a supplier on your own.

Who would enjoy a Cuba tour?

Anyone who loves art, music, unique cultural experiences and great architecture. Cubans have so much passion and it really shows in the arts. Friendly faces are ready to welcome you. Cuba is also a highly educated population which makes it even more fascinating for Cubans and Americans to learn from each other.

Flights to Cuba

There are now direct commercial flights to Cuba on JetBlue, American Airlines, Delta, United Airlines etc from cities like Miami, New York, New Jersey, Los Angeles and Atlanta. Please contact our sales professionals for more details.

What should I pack for Cuba?

Please remember to bring all of your prescription medications in their original bottles. You should also bring over the counter medicines such as Aspirin, Advil, Pepto Bismol, Immodium etc. in case you need them. These brands are not available in Cuba.


Get in Touch with Us

    Call us today for legal travel & $200 OFF our packages booked by May 15th Departures weekly through 2025!
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