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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We chose Cultural Island Travel for our first trip to Cuba in July this year and it was an excellent choice. Very good service from the very beginning, they listened to what we wanted and helped us with planning things accordingly. Our trip to Havana and other places in Cuba was very interesting and enjoyable. Our group was small (we prefer to travel with smaller groups) and our guide, Ebony took fantastic care of us.
I really hope I can repeat my Cuban adventure sometime in the future and when I do I will choose the same company for making my next trip possible. Thank you very much!
Response from Cultural Island Travel - Travel To Cuba LegallyOct 22, 2017
Dear Ela,
Thank you for reviewing your trip to Cuba. We love to plan small, intimate trips for you to be able to see the real Cuba at your own pace. I am glad to hear that Ebony showed great care on your trip. She is one of our most well reviewed tour leaders and cares about our clients happiness so much. We would love to plan another trip to Cuba for you whenever you are ready!
Many thanks,
Shabi Samoohi
Director
Cultural Island Travel
NS
Natasha S. W.
Best Birthday Trip!
Where do I even start...this year I turned 40 and I wanted to celebrate it in a monumental way. What better way than for myself and my sisters, blood and not blood, to travel to Cuba for 6 amazing days in a country I never thought I would see in my lifetime. The team at Cultural Island Travel were very accommodating and attentive to all of my questions, concerns and request. Shabi, is amazing. She has such a heart and passion for Cuba, that you can feel it through the phone when speaking to her. Once I let her know why I wanted to go and the significance of the trip, she when out of her way to make it happen. She assigned us the BEST tour guide ever...Ebony was absolutely, positively AMAZING! The country, the people, the food, and the history was breathtaking. We all learned so much and are forever changed. Thank Cultural Island Travel for making my birthday truly one to remember.
Response from Cultural Island Travel - Travel To Cuba LegallyOct 22, 2017
Dear Natasha,
It was absolutely a pleasure to plan your birthday trip for you and your lovely group of friends. I just spent my birthday in Cuba and loved it so much. It was really my most special birthday. I am glad that yours was also a great success.
I am so glad that Ebony showed you such a wonderful time. We hear these kind of comments all the time about her and are not surprised. She is so dedicated to making the clients feel at home in Cuba.
Lastly, thank you for mentioning my passion for Cuba. Cuba has been my world for the last 20 years and I hope to have the honor to continue taking traveler's there for a long time to come to experience the island I fell in love with in 1999.
Thank you again Natasha!
Shabi Samoohi
Director
Cultural Island Travel
AB
Anitra Bascom W.
where in the world to go to find adventure and with limited time?
CUBA, where else? Ordinarily tours are not my way to go but for this it was necessary! And how lucky that was. We had a very small group size and were spoiled on every turn with tour guides who loved Cuba and couldn't do enough or share enough about the island. Also, we stayed with families who rented out rooms so we got to know a little more about the island. I was curious about our freedom to walk about. We didn't get a lot of free time as it wasn't necessary. I want to add that this trip was about traveling with my daughter--my goal is that she have a great time. I had concerns it would be not much fun being with a bunch of older people (like her mom).
No problem, she had a great time met a fellow photographer who shared pics with her and our guide was about the same age. I couldn't have orchestrated this trip myself as CIT met all our needs. The guides were like friends and that made it very special. It was great. A quick view of a few of the sights include old havana, living on the Malecon, Trinidad, cigar factory, castle during an art exposition, Hemingway's house where they had a special drink with lemons and sugar cane, so much more--I think you get the drift.
Response from Cultural Island Travel - Travel To Cuba LegallyOct 22, 2017
Dear Anitra,
Thank you again for the taking the time to share your impressions of Cuba with us. We are elated that you loved our guides. The same ones are still with us and have now showed Cuba to thousands of travelers.
I agree that it's nice to stay at Cuba's B&B's. My family prefers them to hotels for the more personalized experience.
I am glad your daughter loved the trip as well. I think that Cuba is a nice place for young people of all ages since it's so safe and the people are so friendly. My 14 month daughter has a ball with all the attention she gets from adults and other kids and all the colors,antique cars, and sunshine. She just loves it!
You are the second person on this page to mention the sugarcane and I agree that it is exceptional!
Many thanks,
Shabi Samoohi
Director
Cultural Island Travel
CR
Charles Richard L.
the best, most human, travel company ever
I love travel. I have been in most parts of the world usually without a tour. I also have been on tours in various countries, mainly with good results, some poor, some great.
Cultural Island Travel is beyond the great ones. I feel I owe them money, or something better than that, beyond their charges, which seemed high before doing the trip.
The company is as human as it gets. The founder is a young woman in love with Cuba and its music. She expanded her love through this tour company, of course the best way to start a business. She hires only like-minded, passion driven people.
Krista who handled our complicated details was a model of warm response, calling me back once at midnight her time to answer a question not deserving that care. She knew me and cared about the details. She listened to what I wanted and did it.
Our guide in Cuba was extraordinary. My family of five, from 3 years old to my 70, fell in love with her, partly because of her nature and partly from her dedication to the Cuban ways. She did not have the normal high pitched personality of tour guides. She had a care for us, an intelligence both emotional and intellectual, which made every part of the trip personal.
It is not Cultural Island Travel’s doing that Cuba is the way it is, the preserved way humans used to live at their best, in the days of kindness on the streets, when innocence was in the air. Cuba was the heart of our week of joy, but it was Cultural Island Travel which presented the people and land the way they should be, without dilution or self-serving distortion of a normal tour company’s ways.
Response from Cultural Island Travel - Travel To Cuba LegallyOct 22, 2017
Dear Richard,
It was lovely to be able to meet you for dinner in Havana. Ebony and I still talk about how wonderful you are. We are happy that you loved Cuba so much that you returned to experience the Havana Jazz Festival with us.
Thank you also for reviewing Krista. She really cares about each clients and their particular needs and goes out of her way to make sure they are happy.
I agree that Ebony is very genuine and knowledgable about Cuban ways. She loves Cuba so much that she moved there from Ireland.
Lastly, I can't agree more about the kindness on the streets, and the way the humans live at their best. The Cuban people are some of the most heartfelt, lovely and passionate people I am proud to know.
Showing the Cuba I love to people like you makes it all worthwhile.
We all hope you are doing well,
Shabi Samoohi
Director
Cultural Island Travel
KA
Kim Ann J.
Excellent service and fabulous trip
Cultural Island did a great job of arranging all facets of my trip to Cuba. They matched me with people I enjoyed and were willing to accommodate any wishes we approached them with.There was the right mix of time spent with our guides and time exploring on our own. I would travel with them again.
Response from Cultural Island Travel - Travel To Cuba LegallyOct 22, 2017
Dear Kim,
I remember the planning stages of your trip and I am so happy that the results were what you expected. I know my friend Jill was on your trip and really enjoyed meeting you. We hope to plan another successful trip for you in the future.
Hope all is well,
Shabi Samoohi
Director
Cultural Island Travel
CA
Christie A.
Better than I dreamed it would be!
I scheduled a trip to Cuba through Cultural Island Travel (CIT) back in May 2015. It had always been a dream of mine to visit Cuba, and the first chance to go, I went! This was my first time traveling out of the country and was nervous about all the paperwork that goes into traveling, but CIT made it so easy! They handled ALL the documents and official paperwork that would have probably not done in time or correctly. All I had to do was get my passport and get to the airport!
Because it was a "group travel" type situation, I traveled alone and met up with other members of the group once arriving in Havana, which I was very thankful for our small group because I know ZERO Spanish, and wasn't sure how I was going to get around without them.
We met our travel guide, Ebony, who was amazing! She made sure ALL of us got to see and do everything we were interested in and made time for things that weren't necessarily on the agenda.
For some reason, I was under the impression that the whole time I was there, that I would be supervised, but I was pleasantly surprised that we had free time to be on our own and really EXPLORE the city!
I went on the "People to People Havana Weekend" Tour and in just a few days felt like I really got to experience the culture of the city first hand! The people were friendly, the architecture is beautiful and the mojitos were great too! I am planning to return again soon...and learning some Spanish before I go this time! : )
Anyone who is looking to visit Cuba, I would definitely recommend CIT for an authentic experience!
DL
D L.
Outstanding...
I assumed that Cultural Island Travel would have a difficult time of it when planning this trip. I wanted to see Cuba, January 16-22, 2015. With 11 close friends. Mostly coming from NY, but we had one friend was coming from the Midwest and the another from Europe. In addition, not everyone from NY was traveling on a US Passport. None of this was an issue.
Then we said, we wanted an authentic experience. We weren't looking for an all inclusive 'removed' vacation where we witnessed the country instead of experiencing it. We got that as well. The restaurants we ate at were a mix of paladars (privately owned restaurants run out of homes) and other incredible restaurants with delicious food and outstanding views. We stayed in rented apartments instead of hotels. We met local musicians and had private concerts. We toured the city of Havana with informative tourguides. We met local artists and visited a town made completely of mosaics.
In addition, we went to Trinidad...a UNESCO world heritage site...and a Spanish colonial town that looks like it hasn't been updated since 1850. Cobblestone streets and horses as the main means of transportation, we experienced horseback riding and waterfalls. We ate with locals and drank the freshest sugarcane drinks I've ever had.
I cannot say enough how wonderful Cultural Island Travel was in dealing with such a large and diverse group of people. They custom tailored a trip to our specifications and the tour guides were all incredible.
Response from Cultural Island Travel - Travel To Cuba LegallyOct 22, 2017
Dear D L,
Thank you for the taking the time to write such a thorough and thoughtful review of your trip to Cuba. It was wonderful to show your group of friends the Cuba I have loved for so long. I am so glad that you enjoyed the music and the arts that Cuba is renowned for. I personally love Trinidad so much as well. Nothing beats it's beautiful cobblestone streets and locals riding on horses as well as it's gorgeous mountains and beaches. It is one of the most unique places I have seen and it was lovely to share it with you. I am glad that you also mentioned the Havana city tour. Havana's unique and magical UNESCO heritage sites are best seen through the eyes of an architectural specialist.
As I am writing this I am missing the sugarcane juice from the Cuba's amazing and organic sugar crops as well!
We hope to host you and your friends again in Cuba soon!
Shabi Samoohi
Director
Cultural Island Travel
JR
Jessica Rose H.
Amazing Experience!
From the time of booking my trip until the final ride back to the airport in Cuba my trip was wonderful. Well organized and very friendly staff. Culture Isalnd Travel gave me an unforgettable experience. I would recommend Culture Island to anyone who would like to experience Cuba's beautiful people and culture.
Response from Cultural Island Travel - Travel To Cuba LegallyOct 22, 2017
Dear Jessica,
I remember meeting you at a Cuban music event I organized in New York City. I am so glad that you decided to follow your passion for Cuban music and go to Cuba. I am glad Ebony took such great care of you and I wanted to thank you again for the longer review you sent me about how much Cuba meant to you. It still makes me happy to read it two years later.
Hope to see you soon at another Cuban music concert or in Cuba!
Shabi Samoohi
Director
Cultural Island Travel