About Cultural Island Travel - Travel To Cuba Legally
Has Cuba captured your imagination? Do you want to see a country that is in every way set apart from all of the others? Travel with us to this enchanting island full of friendly faces and discover why even our most seasoned travelers call Cuba their favorite country. Fall in love with an island of people who put the arts first. Meet Cuba’s finest musicians, artists, and dancers. Visit inspiring community project leaders and entrepreneurs. The treasure of Cuba is its people, and you will meet these spirited people that make Cuba unforgettable. You will benefit from our exclusive connections forged since our involvement with the arts in Cuba began in 1999, when our director first witnessed the extraordinary musicianship on the island. At Cultural Island Travel, our sought-after unique experiences lead to a journey of a lifetime. Ask us about our custom tours where we can creatively craft an itinerary based on your group’s interests and budget. We have recently taken amazing musicians such as Questlove.We have no minimum passengers on our custom tours. Contact us at 1-800-494-1945 or [email protected] so we can plan your unique Cuba trip!
Cultural Island Travel - Travel To Cuba Legally (culturalislandtravel.com) has 184 customer reviews on Five Star Index, with an average rating of 5.0 out of 5.
Also known as
culturalislandtravel.com
Website
culturalislandtravel.com
Category
Activities & Tours
Location
New York, New York
Listed on Five Star Index
2026
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The company replied to 29% of reviews.
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Most recent review: October 2026.
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I just returned from Ireland, where we had a James Joyce-themed weekend, followed by five more days all over the country. It was one of my best trips, and all of the planning from Ebony at Cultural Island Travel was perfect! She was with us all the time and arranged for us to meet local people and guides in every city. She was amazing, fun, and knowledgeable. We learned so much about the country and had experiences that would not have been possible without her. I am still smiling as I relive the trip. Thank you, thank you. Thank you!!!
BE
Bernice
Ireland with Ebony was amazing and that…
Ireland with Ebony was amazing and that goes for both the James Joyce weekend and the tour around the country. Not only had she chosen excellent sites and guides, but she brought her good humor into every situation. As far as the auto tour itinerary, I was very glad to have added Belfast because my concept of the country wouldn’t have been accurate or as fascinating without it. Then, to Galway and back, we had wonderful experiences with little lambs and a sheepdog, and then a formidable falcon and falconer at Hawk House. Of course the monuments and castles, the universities, the coastlines, the drystone walls amidst green landscapes were as impressive as the lambs in arms, just not as cute. Thanks also for all your help getting me signed on before the trip. If I decided to go to any of the other destinations, I would certainly go with Cultural Island Travel.
KU
Kush
Absolutely fantastic trip to Cuba
Absolutely fantastic trip to Cuba. Teresa organized everything perfectly, from the hotel and tours to the restaurants and experiences. Our guide Ivan was outstanding, and the drivers were excellent as well. Every tour was private, personalized, and thoughtfully planned.
We took salsa dancing and cooking classes, enjoyed a private performance from a choir and dance troupe, explored Havana and the countryside, and learned so much about Cuba’s history and culture. The most meaningful part of the trip was meeting the Cuban people — incredibly resilient, welcoming, and proud despite the country’s challenges and history.
Cuba has so much untapped potential. It’s a beautiful country with an amazing energy, vibrant culture, and unforgettable people. This was truly one of the most unique and memorable trips I've taken.
VI
Vik
Havana Good Time in Cuba!
We just returned from Cuba and had an incredible experience. From the very beginning, Teresa was responsive, organized, and ensured we had all the information and documents needed before departure.
The itinerary was thoughtfully planned, and our guide, Ivan, was outstanding. He shared so much insight into Cuba’s history, culture, and the daily lives of the Cuban people. We enjoyed exploring different neighborhoods in Havana as well as the beautiful countryside.
The accommodations and meals were excellent, and the cultural experiences throughout the trip made us feel truly welcomed and immersed in the local culture.
We highly recommend visiting Cuba and traveling with Cultural Island Travel. It was an unforgettable and deeply rewarding experience.
TV
Timothy Van H.
Third visit to Cuba
Third visit to Cuba, second with CIT. Returned in part because of - and specifically asked for - Irma, superlative tour guide. Friendly, helpful, and very accommodating. Chosen hotel, dining choices, and activities were impeccable. And, she and driver (Adamo ??) were good company. Recommend without reservation. Hope to go again.
TK
TKnyc
The Cuba trip with Blue Note and CIT was amazing
The Cuba trip with Blue Note and Cultural Island Travel exceeded any expectations we had before going. We stayed at a beautiful hotel with first rate hospitality, ate at one wonderful restaurant after another and everyone we met was warm, welcoming and eager to share about their country.
The trip was well organized, all guides were highly knowledgeable and friendly, always accommodating to our needs. We asked to see a local synagogue and they made it happen and then others on the trip who wanted to go as well joined us. Everywhere we went we met open, friendly hosts and people who were excited to share about their lives. Art galleries, markets, street life, was all a wonderful experience
The music was first rate with our host Jorge Pacheco , in different venues, from rooftops to clubs to music schools and the opera house. He brings a warmth and connection to people that added to the wonder of the trip. We still cannot believe how much we got to do in six days. Nothing rattled our tour guide, Ivette! She was fun to be with the entire time. We felt welcomed, cared for, and well taken care of from start to finish. We will go back with CIT and Blue Note Travel as soon as we can, maybe even next year!
TO
Toni
Incredible experience
I’m not sure what I can say that has not already been said about this amazing company and Cuba in general. My love for the country stretches back 46 years, when I lived in Miami during the Mariel boat lift. I met, worked with and befriended many Cuban people during that time. They are warm, gracious, resilient in the face of often challenging circumstances. I visited the country for the first time in the early 2000s. The year I was there, was also a tumultuous time for the relationship with the US government. Fast forward to March 2026, and here we are! Our trip was very well arranged by Cultural Island Travel (we plan to use them again for a couple of other trips we are considering). We stayed in a lovely casa particular, La Reserva. Our meals were taken in some wonderful paladares (Casa Mia, Cha Cha Cha etc), we toured an organic farm and then had a cooking lesson at Cafe Ajiaco, we visited the handicraft market, the antique shop. Did an hourlong ride in a beautiful pink convertible. Even though we only visited Havana during our trip (I had visited other parts of the country during my last trip there), I felt like we saw and did so much, we really gleaned a solid foundation for future travel there (yes, I want to return for sure). Our guide Laura was fantastic, as was our driver, Jordan. Despite the fact that there are currently serious challenges (lack of fuel being the main one), I’m happy that we decided to go, as everything we did while we were there provided direct support to the Cuban people. I hope I am able to return again.
EH
Embry H.
My recent trip to Cuba with Cultural Island Travel
The Cultural Island guides and staff are incredibly smart, helpful, and just very nice people. They made my recent trip to Cuba enjoyable and educational. In spite of the difficult political situation, and the difficulty concerning fuel and electricity, they worked through any issues and made us feel safe and welcome during the whole stay. I was very comfortable in my accommodations, and I learned a lot about Cuba and its art and music. I wholeheartedly recommend traveling with this group, which has many different destinations, not just Cuba.