Everything you need to know about Cuba!

Is it legal to Travel to Cuba?

How is CIT travel to Cuba legal?

Cultural Island Travel has taken thousands of travelers to Cuba legally. We design itineraries that are fully compliant with the OFAC guidelines for the Support for the Cuban People category, including activities such as music and dance performances, artist visits, meals at private restaurants, and more. Tours are open to all US citizens and residents, and no application process is necessary. We are currently authorized to take any American to Cuba under a general license and our OFAC approved itineraries make sure that your travel is fully legal. Support for the Cuban people means you will have the chance to meet the local people of Cuba and have meaningful interaction with them. 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," which means you need to maintain a full itinerary of activities each day. When you book a trip with CIT you can rest assured that your trip is legal; we will provide you with an itinerary that meets all the requirements and prepare your visa and certificate of travel to Cuba ensuring ease of re-entry into the US.

Why should I travel with CIT?

CIT has over 15 years of experience with Cuba and its culture. We represent musicians in Cuba and provide our travelers a rare glimpse of the real Cuba. We are not interested in a cookie-cutter itinerary but rather a set of unique experiences, hand-picked to showcase the best people and talents that the island has to offer. We want you to see the real Cuba that we fell in love with in 1999 and watch you fall in love with it too. For more info see our about us page and our interview with our Cuba expert on our home page.

What does Support for the Cuban people travel mean?

Support for the Cuban people travel is the category under which Americans can visit Cuba.

A traveler is required to provide support for the Cuban people and promote independent activity intended to strengthen civil society in Cuba.

A traveler is required to engage in a full-time schedule of “Support for the Cuban People” activities. These include:

  • Meeting with local artists, tobacco manufacturers and people who run their own business
  • Meeting and engaging with musicians at a performance
  • Explore independent museums
  • Independent markets
  • Dance classes
  • Art shows and private galleries
  • Discuss Cuban culture and society with locals

You must retain records, like receipts and itineraries, and keep them on file for five years.

A traveler must avoid all transactions with a military owned business.

Why is this the best time to go to Cuba?

It is only the third time since 1963 that Americans have been permitted to travel to Cuba legally. Visit Cuba before it changes, the time is now!

General Tour & Cuba Questions

Who would enjoy a Cuba trip?

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.

Is there a minimum group size?

No, with Cultural Island Travel there is no minimum group size. Groups average at 10 passengers. If you have a group or organization we can discuss custom tour options that are appropriate for your budget and interests. We have conducted trips for conventions that have hundreds of attendees.

May I go to Cuba with CIT and not a group tour?

We can arrange travel for small, custom groups but if you are joining one of scheduled tours they are group tours. The upside of this is that many clients make excellent friends with their group of like-minded travelers and these friendships last many years. We have had many passengers who want to return to Cuba with new friends they have made on previous tours.

How long in advance must we book a tour?

Due to Cuba recently being featured in the news and listed on several top 10 lists of best places to go some airline and hotel availability is limited. We have been able to book last minute tours through our wide network of contacts but hotels and B & B’s are in short supply and have increased in price. The high season in Cuba was November through June and now it’s all year round. If you need to go last minute or anytime in the next year please call us to start planning as soon as possible so that you have the best choices for flights and lodging available to you.

What age groups normally go to Cuba?

Typically the age range is 30’s to 60’s but all ages are welcome.

Do Cuba tours sell out?

Many Cuba tours do sell out. Approximately 300,000 American travelers went to Cuba in 2015 legally and this number continues to grow as more Americans become aware of this exciting new way of traveling to Cuba legally.

Will I have any free time in Cuba?

Yes, free time is available generally in the early morning or in the late afternoon and evening on our tours. Our expert staff is very much in tune with the music scene and will research activities at night for those who are interested in jazz, salsa, ballet, cabaret such as the Tropicana or many of the hundreds of wonderful music and dance events that Cuba offers as part of its nightlife. We also leave some nights free for you to explore the wonderful private restaurants that Cuba has to offer. We always have lists of things to do or the best places to eat during your free time and would be happy to make reservations for you. During the day we will have a schedule of outstanding cultural activities for you.

What is the price of a Cuba tour?

Each tour is priced differently depending on the length of the tour and the geographical areas covered. Please call us for our current pricing. Also, for custom tour we price them depending on the activities you are interested in. Please contact us for more information on custom tours for your organization, family or friends. It is almost impossible these days to know exact pricing before we speak to you and assess your needs as well as what time of year you would like to travel.

Are Cubans friendly towards Americans?

The answer is a resounding YES! Cubans love to exchange ideas and conversation with Americans. Cubans are very friendly people and are well versed in many aspects of American culture!

What are the best cities in Cuba?

Here is a list of some of the most popular cities to discover on our tours:


Havana is one of the most unique, atmospheric places on the planet. The people, the architecture, the music, the history, the art— it’s an amazing place to visit. Many Cuban musicians have written songs as homage to Havana. No trip is complete without a visit to Havana.


Nestled between the ocean and the mountains, Trinidad is Cuba’s best example of a colonial town, and it has been wonderfully restored with funding due to its UNESCO status. Trinidad, Cuba is a photographer’s dream with many narrow cobbled streets to wander.

Santiago de Cuba

Set between the Sierra Maestra mountains and the coast, Santiago de Cuba is Cuba’s second biggest city. Santiago de Cuba has more of an Afro-Cuban feel than Havana and the passion for salsa and carnival are greater here. Its coastline is nothing short of spectacular. Stop off at Casa de La Trova for beautiful Buena Vista social Club music.

Pinar Del Rio

The Province of Pinar del Rio to the west of Havana offers a wonderfully different Cuba holiday. Pinar del Rio was founded by a Spanish general captain in 1774 and currently has 70 000 inhabitants. It is part of the quiet and lovely Cuban countryside where sugar and tobacco are grown. It boasts amazing natural caves as well.

Cayo Santa Maria

Virtually untouched, the little island of Cayo Santa Maria is part of the Jardines del Rey archipelago to the north of the central province of Villa Clara and its peaceful semi-deserted beaches and surroundings make holidays in Cayo Santa Maria the perfect peaceful retreat away from it all. Part of the Bahia de Buenavista ecosystem, it has been declared by UNESCO a Biosphere Reserve with its predominance of lush vegetation and immaculate beaches. A true paradise to rest and relax surrounded by nature, Cayo Santa Maria is an unforgettable experience. While at Cayo Santa Maria discover the culture of the nearby fishing villages and the city of Santa Clara.

How do I book a Cuba tour?

You can email us at info@traveltocubalegally.com or call us at 1-800-494-1945 and we can book your trip by phone.

Immigration & Customs

Flights to Cuba

What should I pack for Cuba?

Currency, Tipping & Gifts

Documentation Needed to Travel

Safety, Insurance, Food & Water

Photography, Video, and Electronics

Language & Resources

Do I need to speak Spanish to go to Cuba?

Many Cubans that you will interact with speak some English. You will be accompanied by a bi-lingual guide who will be able to make any necessary translations. Most of our participants do not speak Spanish and it is not at all necessary for travel to Cuba.

What programs would you recommend in the event that I would like to learn some Spanish before my trip?

Here are some recommended options for learning some Spanish before your trip.

-Most guidebooks have some basic Spanish phrases

-We find the book 500 Spanish verbs by Kendris Chris very helpful, see link below


For more in depth courses please see the following resources:

Rosetta Stone Spanish Course http://www.rosettastone.com/

Pimsleur Spanish course http://www.pimsleur.com/Learn-Spanish-Latin-American

The best way to learn is to practice with the locals. Come visit Cuba with us and learn some Spanish “A lo Cubano”-The Cuban way!

Culture: Music, dance and fine arts

Why do we believe that the Cuban arts are amazing?

In the United States most parents want their children to become doctors or lawyers. In Cuba doctors are respected but every parents dream is that their children become musicians. Music is the most respected profession in Cuba and one that many aspire to. At an early age Cubans can audition for music conservatories. Once selected, they go to the conservatories through 18 years of age and then if they choose to continue they go to a masters or doctorate program at a school such as ISA (Institute of Superior arts). ISA is comparable to the Julliard School of music. All schooling is free in Cuba for Cubans. It is interesting to note that at ISA no salsa or jazz is taught. Students receive strict classical training and then learn these genres on their own. This really pays off and creates some of the best musicians worldwide. We have strong relationships with these musicians. We want to introduce you to them and show you their passion, talent and expertise. We work with young up and coming jazz artists like Jorge Luis Pacheco who sat in with Wynton Marsalis and the Jazz at Lincoln Center Orchestra to seasoned musicians like Cesar Pedroso who co-founded arguably the best band in Cuba, Los Van Van over 40 years ago and now heads his own 15 piece salsa band. We also have in depth connections with the best dancers and fine artists in Cuba and they can’t wait to meet you!

Weather in Cuba


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!


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