Bespoke Cuba Travel: a Cuba travel experience like no other.

Bespoke [bəˈspōk] dealing in or producing custom-made articles; an exclusive design for a particular customer or user.

Cuba [kyoo-buh] The Antilles’ largest island, is an archipelago of 4,000-plus islands, islets, and cays. They are traced by hundreds of miles of white powdered beaches. Cuba is uniquely surrounded by the Caribbean Sea, the Atlantic Ocean and the Gulf of Mexico. The island is home to an impressive ecosystem, including natural biosphere reserves, fauna refuges and crystal-clear lagoons, to rolling mountains and rainforests. Additionally, Cuba is home to the world’s second pristine coral reef. Cuba tops two of the travel industry’s most disparate lists; the shrinking list of Emerging Destinations and the list of Endangered Destinations at risk of losing their rich cultural heritage in the face of rapidly increasing tourism. Cuba plays a complex role in the cultural lexicon of the United States. Americans relate to her classic American automobiles, baseball, and boxing, in addition to Hemingway, the Cuban missile crisis and Fidel Castro. The island nation’s superlative education system, UNESCO sites, and achievements in medicine are internationally renowned. Cuba is full of romance and magic. An intriguing history of smugglers, slavery and buccaneers, to sugar barons, conquistadors, and communism. Few islands in the world can boast such a profound yet enigmatic identity.

Travel [travəl] an expedition, a journey.

About Us

For over 26 years the virtuoso team of Cuba travel designers at Bespoke Cuba Travel have created unparalleled Cuba travel encounters to one of the world’s remaining travel frontiers. We craft breathtaking tailored Private Designer Expeditions for explorers accustomed to a more resplendent style of travel.

At Bespoke Cuba Travel we ardently listen to our guests. We meticulously plan and rehearse the logistics of your voyage. Our Cuba travel style tends to details overlooked by most “luxury” Cuba travel providers. We are prepared to anticipate your needs and realize your wishes. No matter how rare or challenging. We strive to redefine your notion of what is possible on a holiday.

Our ethos is to improve the lives of the Cuban people. The Bespoke Cuba Travel adventures we offer provide guests a multitude of opportunities to do just that.

If your wanderlust yearns for a Cuba travel journey far beyond the reach of other Cuba travel companies. Where the Cuban people welcome you instead of entertain you. We invite you to join us and discover a Cuba as seen by few. To learn more about us, contact us.

René Peña

Our Motto

More Cubans; Fewer tourists.

At Bespoke Cuba Travel We are committed to distance you from other tourists and the traps they fall into to ensure your unique venture is fashioned alongside Cubans from all walks of life.

What Bespoke Cuba Travel Offers You

Cuba is not a destination where one can travel alone guidebook-in-hand. Experiencing it on a prepackaged motor coach tour with 25 other strangers is also not ideal. Both will result in an insulated cartoon-like perspective of this precious island. Bespoke Cuba Travel offers you a better way to savor Cuba.

Our private expeditions let you realize unimaginable moments and exceptional memories with a casual style of luxury. You will experience the complex tapestry of Cuban life among its unique people. You will gain first hand insight into their mastery of hope, resiliency, daily obstacles, and curiosities. Be welcomed at local birthday parties and weddings. Join them as they collect their food rations and walk their children to school. You can also visit them at work and cook meals together.

Included in all our tours;

  • Cuba tourist entry Visa
  • All Havana airport and hotel transfers via a chauffeured convertible vintage car
  • All ground transportation
  • Deluxe accommodations
  • Unlimited beverages including alcohol at lunch and dinner
  • Specialty guides, instructors, translators and trip assistants
  • Entrance fees to all attractions, exhibits, concerts and special events
  • Weekly laundry services
  • All meals (no menu limitations) at Cuba’s finest restaurants
  • The services of a bilingual Journey Guide
  • All necessary supplies and equipment rental
  • Unlimited Internet access (where available)
  • Portfolio with a fully chronicled tour history confirming your trip provided
    “Support for the Cuban People.” The US Government requires you keep this information for
    5 years
  • All Taxes and Gratuities

Private Designer Expeditions

It’s time to elevate travel out of the ordinary. With Bespoke Cuba Travel you can discover the ultimate in Personalized Private Travel with a casual style of luxury.

Some travelers enjoy bespoke travel. There are discerning travelers, however, that look ahead to once-in-a-lifetime tailored extravaganzas. Our ambition is having an in-depth understanding of our client’s expectations and using our local expertise to hand-craft a selection of intimate experiences perfectly tailored for our clients. When it comes to delivering the voyage without equal, the paramount factor is turning your dream into a reality. Whether it’s To’ak chocolate and Veuve Clicquot marshmallow smores while on one of Cuba’s uninhabited islands, to calling on Cuba’s many ports on a catamaran. Your travel designer will listen to your ideas and talk to you about what you enjoy most so they can identify the most important aspects of your trip.

Once we’ve consulted with you on the phone, we begin designing your journey. Within a few days we will send you a preliminary draft of your bespoke itinerary. This will include your flights and accommodation, a brief description of any tailor-made tour suggestions and the total price.

The idea is for you to read through your draft bespoke itinerary to see if you like the general idea of it, to determine if we are on the same page. At this stage nothing is booked, so if you choose to switch your accommodations or replace any itinerary suggestions, you’re free to do so. In fact some clients make changes to their itinerary right up until the eve of their trip. The opportunities are endless when it comes to your bespoke itinerary. The whole objective is that the final say is yours – we want your unique Private Cuba adventure to be the voyage of a lifetime! Contact Us today to start designing your private tailor-made Cuba journey.

Sample Journeys we have designed for past clients

Cuba Explorer

14 Days / 13 Nights

Wander Cuba

10 Days / 9 Nights

Discover Cuba

7 Days / 6 Nights

Havana Experiential

4 Days / 3 Nights

Havana New Year's Eve 2023

4 Days / 3 Nights

The Bespoke Cuba Travel Advantage

We are native Cuban and Cuban Americans. For nearly 26 years we have married our Cuban culture, incomparable relationships on the ground (some are family members) and voyager ingenuity to blaze new trails with each journey.

A truly Bespoke Journey

Your itinerary will not be a sequence of timed activities (the people in Cuba have a laissez faire association with time anyway). Every tailor-made experience we create is unique as the person we create it for; your very own once-in-a-lifetime Cuban adventure. Share your curiosities, interests, imagination and travel requirements with us and we will design a one-off Cuba encounter that will amaze.

Private tailored travel

Some explorers prefer custom-tailored experiences, concierge service, and unique amenities. We are ready to realize the most unique.

The Bespoke Cub Travel promise

We are committed to making the Cuba we love and cherish as memorable and precious to those who experience it with us.

The Bespoke Cuba Travel Personal difference

Courteous Service

Enjoy special attention from the moment you contact us with your inquiry to long after you’ve returned home. We take care of all the logistics and details before, during and after your trip.

Personal Attention

Along with your trip designer is a handpicked and well-educated native support team. It includes travel assistants, translators, and drivers, to culinary managers and expert specialty guides. They are ready to offer You gracious service. Our 1:2 crew member to guest ratio guarantees you a premium comfortable journey.

The best all inclusive policy available in the Caribbean

Unlike our peers, all your meals are included including alcohol. There are no menu restrictions. Enjoy unlimited breakfast, lunch, nightly cocktail hour, and dinner. And you can choose where you want to dine. Read about a paladar (restaurant) in a guidebook or on the web? It’s included. Your voyage is All-inclusive…even once-weekly laundry service.

Reasonable Pricing

Price Matching

If you find another Cuba travel company that offers the same package at a lower price, we will match their offer plus give you a $200 discount.

Generous Discounts

We offer generous discounts to AAA and AARP members and young ‘explorers’ under the age of 12. Cherished members of the U.S. Military, first responders and their families. Please be sure to request your discount when you first contact us.

We do Good

At every turn, we work independently of hotel chains, airlines, and attractions owned by Cuba’s military. Instead, we contract directly with entrepreneurs, owners of casas particulars (B&Bs), paladars (private restaurants), drivers, chefs, and farmers.

Meaningful integration

Other tour companies take tourists to the most popular attractions in Cuba’s most popular cities. We guide you off the beaten path and provide you an opportunity to improve the lives of the Cuban people. You get to know the Cuban people on a more conscientious level.

Legal Travel To Cuba

Many people ask, “Can Americans travel to Cuba?” Despite what you may have heard the answer is, yes. It is ‘very’ legal for US citizens to travel to Cuba. Hundreds of Americans visit Cuba everyday (currently there are nearly 20 daily non stop flights to 9 Cuban cities departing from Miami, Tampa and Houston). And when it comes to the Cuba travel excursions Bespoke Cuba Travel offers, they all strictly adhere to the US State Department and the US Treasury Department’s Cuba travel policies.

The governmental organization responsible for regulating travel to Cuba for Americans is the Office of Foreign Assets Control (OFAC). OFAC requires that your Cuba trip be booked and guided by an authorized tour company based in the United States (like Bespoke Cuba Travel). Under OFAC regulations, any individual may travel to Cuba without any government documentation or permission in advance if the purpose of their travel falls under one of the twelve legal licenses. There is no actual paper license issued. It works on an honor system. If the purpose of your Cuba travel falls under any of the twelve pre-approved Cuba travel licenses then you can visit Cuba. It’s that simple.

The 12 licensed categories are:

1. Family Visits
2. Journalistic Activity
3. Official Business of Governments or Certain Intergovernmental Organizations
4. Religious Activities
5. Support for the Cuban People
6. Academic Educational Activities
7. Activities of Private Foundations, Research or Educational Institutes
8. Public Performances, Clinics, Workshops, Athletic Competitions and Exhibitions
9. Humanitarian Projects
10. Professional Research and Professional Meetings
11. Exportation, Importation, or Transmission of Informational Materials
12. Certain Authorized Export Transactions Special Category.

Most of these categories are very narrow in scope, meaning few Americans qualify for them. However, the Support for the Cuban People category permits any American to legally travel to Cuba. Travelers must engage in a full-time schedule of activities intended to enhance contact with the Cuban people and support civil society in Cuba. Activities that provide “Support for the Cuban People” can range from eating in privately-owned restaurants and visiting local artists to spending money at private businesses owned by Cubans and staying at a casa particulares (B&B) instead of hotels.

US Travelers are still able to spend unlimited amounts of money throughout the island and bring back nearly anything they wish exept tobacco and alcohol products (provided they do not exceed State Department and US customs limitations).

Shortlyt after you return home, you will receive a report from us including copies of all the receipts associated with your trip. The report also includes the schedule of your respective activities, proof that you patronized businesses owned by Cubans, etc. OFAC requires you to keep this information for 5 years. We are the only Cuba travel provider that provides guests with such an exhaustive record.

The most recent change to US Cuba Travel policy requires that you must avoid staying at hotels owned by the Cuban military and banned by the US State and Treasury Departments. Bespoke Cuba Travel will lead you away from these hotels. In addition, there is the Prohibited Financial Transactions List. This list forbids Americans from spending money at businesses owned by the Cuban military and communist party officials. Compared to everything Cuba has to offer, this list is very small. It represents less than 1% of the business on the island. The objective is for travelers to do business directly with Cuban owners of small businesses as opposed to entities that would disproportionately benefit the regime at the expense of private enterprise. Bespoke Cuba Travel will guide you away from those entities.

If you have further questions about how Americans can travel to Cuba legally you can Contact Us for more information or call the Treasury Department directly at 1-800-540-6322 Press #5 for the Cuba Travel desk then choose option 1, 2 or 3 (it doesn’t matter which one). At the end of the message press the * button on your phone and you will be connected. They are very helpful (you will likely be asked to leave a message; they respond quickly).

In conclusion, Legal travel to Cuba is a little cumbersome however, not as overwhelming as it may seem. It’s definitely worth it. Any American can visit Cuba and we will make the process of obtaining a Cuba Travel Visa a simple and seamless one for you.


  • We rarely opened our wallets except to purchase cigars and trinkets. Everything was included and the food was delicious. We were recommended by Jackson White. Jake March
  • Everyone is very nice. They go out of the way to make you feel special. Many surprises throughout. Lana & Joseph Carry
  • Laz noticed our son had lost interest in the trip. So, he paired him up with a mime who taught him the art. He also arranged for him to help feed a couple of animals at the zoo. Naomi
  • The best part was an outdoor movie dinner night with the actual filmmakers. The films were projected onto a big rock. We had “Cuban smores.” We def recommend them. Jackie and David Meyer
  • My husband is a pilot and I’m a retired flight attendant. We travel extensively. This tour was one of the best we have ever joined. Martha
  • The Minister of agriculture was our guide at a tobacco farm. He then took us to a sugar cane cooperative. He then invited us to his home for dinner (and great cigars!). Jackson White
  • Thank you both for showing us such a great time. Luis, we want to particularly thank you for planning an itinerary that allowed us to go salsa dancing every night. Again, thank you. Andres & Silvia Spelling
  • We saw Cuba in a way that was more authentic than the one our Lonely Planet guide offered. Amber
  • They pampered us lots. We helped Cuban teachers improve their English. We had a great time. Gabe
  • My daughter and I visited Rosa’s house in Havana where she played guitar for us. She also taught us how to make frijoles. Amy and Susan Barge
  • This was a very special trip. Debbie Cohn
  • The professors and specialty guides were first-rate. Music & food also were terrific. Toni Nolan
  • The Cuban lamb pastries and the paella were delicious. Ben and Jerry’s should get their hands on their recipe for candied papaya fruit ice cream. There was so much delicious food and off the beaten path experiences. August and Melissa Pitt
  • There’s a schedule but it’s flexible depending on your interests. We indulged in their wonderful meals. Jason Carmella
  • The evening meals were spectacular. We keep in touch with a few of the Cuban friends we made on the tour. Émile Truffaut
  • I was impressed with how much time and effort they put in to finalize our itinerary. We requested many changes to it and they didn’t seem to mind. This is an impressive group that knows all the hidden gems throughout Cuba. Two thumbs up! Jake Morris

Contact Us / Reserve

    × How can I help you?