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 worked with Teresa who organized an amazing trip to Havana. This was an eye-opening experience and I travel a lot. What an amazing country, great people and great culture. I highly recommend using this service working with Teresa and visiting Cuba.
MM
michael M.
Fantastic cultural/culinary tour
I called 3 travel agencies when planning a trip to Cuba for our family, and Teresa was so helpful that I had to go with CIT. She was unfailingly courteous and on top of everything. When we arrived in Havana our wonderful guide Irma met us at the airport and led us on a whirlwind tour of cocktail mixing classes, dance shows, cooking classes, concerts, museums—even when we made last-minute requests, she was able to adapt our schedule with no problem. Everywhere we went, we were treated like celebrities. If you’re going to Cuba, you can’t go wrong with CIT!
JM
Jimmy M.
This was my fourth trip to Cuba with…
This was my fourth trip to Cuba with Cultural Island Travel and they are outstanding! Theresa with CIT arranged a wonderful Cuban adventure for me. My guide, Ivan Leon, was extremely informative about everything related to Cuba. Ivan and William, the best driver ever, picked me up every morning for my requested cigar and tobacco hunt/adventure. Such a fun day in Vinales! I will return to Cuba and will definitely use Cultural Island Travel.
CS
Charles S.
Beyond our expectations
My wife, myself and a close friend decided to venture to an unknown after hearing from another buddy about CIT and their attention to detail. From the details of travel and Visa, and the continued follow-up from Teresa, to the flight back home everything was simply amazing. We had an idea for itinerary, but Teresa helped fill in what we may like as foodies and Culture enthusiasts. I probably phoned her 7-8 times and she answered every time with info we needed. We got to the airport, and it was love at first sight with our guide and friend forever, Laura. She is creme de la creme, so hospitable and so giving as our guide. Our driver, Kaki, was always smiling ear to ear, and my wife and our friend always greeted him with kisses on the cheek, which he totally enjoyed.
From the drive in the antique convertible, to the cigar, rum and chocolate tasting, to the farmers outdoor market, the flea market, and the special trip to the ocean, the Cemetery tour and the Grand Theater tour, Hotel Nacional grounds walking around and again Rum tasting :)......wow it was all spectacular. I only wish we could have witnessed more live music, but next time we will for sure.
Our B&B host Alex (and the boys) were amazing, his place is a museum unto itself. Accomodations like any 5 star hotel room for sure, and right in the heart of everything. Thank you again Teresa and Laura, for making it a memory for a lifetime.
JM
Jaime M.
Cuba - An awesome experience!
There are many misconceptions about going to Cuba and unfortunately people give their opinions without having firsthand experience of what Cuba is all about.
My wife and I decided to seize the opportunity and contracted with CIT. To say they were awesome, is an understatement. They curated an amazing itinerary, kept us busy every day enjoying and experiencing everything Cuba has to offer; music, culture, sights, sounds and beautiful people.
From the beginning, Teresa was very informative, walked us through what to expect and made the process of signing up very easy. Once we landed in La Habana, we were met by our driver, Carlos (on a 1952 Chevy Deluxe) at the airport and took us to our hotel. The next day and every day thereafter we were greeted by Irma, our friendly and knowledgeable guide. She took us everywhere answering all of our questions and setting up different informational tours with other local tour guides (even horseback riding) who were also very friendly and informative. We got to experience La Habana, Cinfuegos, Trinidad and Las Terrazas where we were treated to many different experiences ranging from local music, dance presentations, vintage cars, excellent food and even got to visit the Tropicana Club. I wish we had more time because I would have loved to visit many other places.
I am glad we contracted with CIT because we wanted a hassle-free experience, and they took care of all of our needs.
A big thank you to Irma Gonzalez who put up with us and treated us like family for a WHOLE 7 DAYS. Cheers!
MI
Marylen I.
This company is great knowledgeable
This company is great knowledgeable. I was able to see my family. I will be able to go back with ease. Any questions or concerns from getting a driver, where to stay, and flights. Teresa was always on top of everything.
HB
Heidi B.
Cuba Is Beyond Expectations
Our trip to Cuba was beyond expectations due to the excellent planning by our guide, Laura, and the hidden beauty of the island. Our bond was instant! From the time she greeted us at the airport, until I cried when we departed, she was amazing!
There is something special about the way the trip was planned to accommodate our pace and allowed us to have the most fabulous experience, leaving us wanting to come back. Laura's knowledge is extensive, and she is open to all types of questions and requests.
We toured many of Havana's sites in style with our wonderful driver, Willy! From the Grand theater to the fabulous dinners, we had great guides and good food. Our two nights in Trinidad really gave us another perspective of the island and its beauty.
I have a lot more travel in me and Cuba is on my list of places that are worthy of a second visit. If only to see Laura again:::::)
AH
Alexandria H.
Our trip was wonderful
Our trip was wonderful! Laura was amazing! We felt so cared for and Laura did an amazing job being responsive to our individual requests and needs. We had two instances where we needed to go to the doctor/ER and she didn’t miss a beat. She made traveling with our two young boys as easy as can be expected, and they loved her. At the airport my six year old hugged her and said, “thank you for being our friend.” 🥹
Before we left, people warned us that the food wouldn’t be good. But, we never had a bad meal. In fact, the food was delicious and a big highlight for us.
Laura understood quickly that we wanted to explore Cuba, but we also didn’t want a packed trip or to feel rushed. As a result, she asked a lot of questions and offered us opportunities to cancel scheduled items in the itinerary. For example, in Trinidad we really preferred to spend an entire day on the beach, and she accommodated that.
The company made an itinerary for us customized to our desires. Our photoshoot was a real highlight for the whole family. We are eagerly awaiting those pictures! I also really loved the Beyond Roots trip with my reading. I would recommend that to future travelers. The kids enjoyed the Ashton Hotel on the last day, but we all agreed that Alex’s Airbnb was easily the best place we stayed. His house is amazing and the pool was exactly what we needed. We swam every single day with the kids!