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

Bespoke [/bəˈspōk/] 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 rain forests. Additionally, Cuba is home to the world’s second pristine coral reef. Cuba travel 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.

Christopher Columbus believed he had discovered a new route to India when he first arrived at Cuba’s Guarda La Vaca beach in 1492. He purportedly stated it was, “the most beautiful land human eyes have ever seen.” Remarkably, he was some 10,000 miles off-course.

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.

Who is Bespoke Cuba Travel?

For nearly 20 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. Our petite-sized semi-guided Cuba travel journeys operate with a maximum of 8 travelers. For explorers accustomed to a more resplendent style of travel, we also craft breathtaking tailored Private Designer Expeditions.

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 so. From sharing professional skills and knowledge to empowering them with donations.

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 entertaining 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 predominantly 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 expeditions let You experience the complex tapestry of Cuban life among its unique people. You will realize unimaginable moments and exceptional memories. Gain firsthand 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;

  • The best all-inclusive policy in the Caribbean.
  • Cuba tourist entry Visa.
  • Cuban customs documentation.
  • Cuban health form.
  • All hotel and airport transfers.
  • All ground transportation.
  • Premium accommodations.
  • Unlimited beverages including alcohol.
  • All meals with no menu limitations.
  • USB with a fully chronicled tour history confirming your trip, “directly benefited the Cuban people.” (US Govt. requires you keep this information for 5 years).
  • A carbon offset donation of your journey benefiting The Nature Conservatory.
  • All Taxes and Gratuities.
  • Artisanal bon voyage gift.

Chelsea London Phillips

Petite Group Journeys

Petite Group Journeys are premium theme-based excursions. Guests are social and tend to travel often. Guests range from millennials and retirees to honeymooners and solo travelers. A maximum of 8 travelers per journey provides an intimate environment. This affords each guest ample personal attention. It also keeps the group under the radar. This provides the group access to locations and events inaccessible to other tour groups. All Bespoke Cuba Travel journeys are semi-guided. They provide guests unique opportunities to break off from the group and realize Cuba in their own special, bespoke way.

Contact Us to learn more about our Petite Group Journeys.

Wander Cuba

10 Days / 9 Nights
From USD $6500 per person
Cities visited: Santiago de Cuba, Camagüey, Moron, Trinidad & Havana

New Year’s Eve 2020 in Havana Cuba

5 days 4 nights including Airfare
From $7500 pp
Limited to a maximum of 12 travelers

Discover Cuba

8 Days and 7 nights
From $5500 USD
Cities visited: Havana, Moron, Trinidad – Sancti Spiritus and Santa Clara

Private Designer Expeditions

Some travelers enjoy bespoke travel. There are travelers, however, that look ahead to once-in-a-lifetime tailored extravaganzas. 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. The opportunities are endless.

Contact Us to discuss your private custom, Cuba Journey.

The Bespoke Cuba Travel Advantage

We are native Cuban and Cuban Americans. For nearly 20 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. Our journeys are semi-guided. This allows us to help You personalize your experience based on your interests and curiosities. This flexibility affords You opportunities to go off and do your own thing.

Private tailored travel

Some explorers prefer custom-tailored experiences, concierge service, and unique amenities. We are ready to realize the most unique private Cuba expedition You can dream of.

 Our Motto

Fewer tourists. More Cubans. While in Cuba You will be distanced from other tourists. Most of your time will be in the company of Cubans from all walks of life.

The Bespoke Cub Travel promise

Every tailor-made experience we create is unique as the person we create it for. Your very own once-in-a-lifetime Cuban adventure. We are committed to making the Cuba we love and cherish as memorable and precious to those who experience it with us. Share your curiosities, imagination and travel requirements and we will design a one-off Cuba encounter that will amaze.

The Bespoke Cuba Travel Personal difference

Courteous Service

Enjoy special attention from the moment You call 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 1:1.5 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. 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 a less expensive and similar package, We will match their offer. Plus give You a $500 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 & their friends and families also enjoy special discounts. Full and partial scholarships are available to select public school students and teachers. Kindly inquire to see if you qualify for a price reduction. You never know.

Price Markdowns

If before your journey begins you find on our website that the price you paid for your trip has been reduced, we will refund you the difference.

We do Good

At every turn, we work independently of hotel chains, airlines, and attractions owned by Cuba’s communist government. Instead, we contract directly with entrepreneurs, owners of casas particulars, paladars, drivers, chefs, and farmers.

 Positive Footprints

Beginning October 15, 2019, Bespoke Cuba Travel will offset approximately 20% of each guest’s CO2 emissions. This will be done by providing financial support to various nature preservation organizations.

Meaningful integration

Other tour companies take tourists to Cuba’s most popular cities. We take You into small villages where You get to know the Cuban people on a more conscientious level.

Volunteer travel

We provide many opportunities for guests to to improve the lives of the Cuban people.

New Year’s Eve in Cuba

A great marvel for any globetrotter is encountering the familiar. Something you can identify with on a foreign land. New Years Eve in Cuba is somewhat a mystery. On the one hand, there are Cubans who celebrate the January 1st, 1959 anniversary of when Castro and his revolution victoriously marched into Havana. On the other, Cubans are hoping the new year will liberate them from the product of that same revolution. Hopes and political persuasions aside, certain things are for sure. Firstly, Cuba for New Years is a rich and lively, familiar set of coordinates for a New Year’s Eve in Cuba celebration. Secondly, Cubans are always ready for a party. In addition, they are eager to celebrate it alongside you.

Bespoke Cuba Travel offers you the new year’s eve in Cuba party of a lifetime. This is an exclusive invitation to visit Cuba for New Years . Where the Cuban people welcome you rather than entertain you. Moreover, don’t wait for too long because this glorious New Year’s Eve in Cuba private holiday is open to only 12 VIP insiders.

For more information click here

Volunteer travel

Volunteer travel is the basis of our ethos. The tenor of our business is focused on improving the lives of the Cuban people. All our trips offers guests opportunities to volunteer travel and support civil society. We offer You a variety of ways to do so. Guests can share their skills, hobbies, knowledge, and philanthropy to empower the most marginalized Cuban people. Regardless of age and capacity guests can enjoy volunteer travel by providing a pivotal and prolific impact on the Cuban people.

Bespoke Cuba Travel contributes positive change in four key areas:

  1. Child Development
  2. Community Health
  3. Entrepreneurship
  4. Hurricane relief


  • 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. Colorado and paella.
  • This was a 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 & Jerry 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 enjoy trekking alone. I chose them because they didn’t charge me a solo traveler supplement. It was fun trip & the food was on great. Kyle Paez

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