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My Private Cuba

Explore Cuba on a small-group tour exclusively for your family and friends.





ENCOUNTER hidden havana

Choose your desired dates of travel and visit Cuba on a small-group tour with your own guest list of family and friends! Gain rare access to luxury villas within the Miramar community, which is gated and private. Experience and taste authentic cuisine at historic paradores. Participate in a hands-on cooking class with a local culinary expert. Immerse yourself in the arts with visits to local artist studios and festive Cuban musical experiences. Enter into a place of literary history with a visit to Ernest Hemingway’s Finca Vigia Estate. Engage with Cuban culture through local artists, musicians, dancers, cigar-masters, culinary crafters, rum distillers and classic car restorers on this once-in-a-lifetime private Adventure to Cuba that will have you reminiscing for years to come!


The “My Private Adventure Program” is perfect for those who prefer to travel to a desired destination while being within a familiar camaraderie of their own family and friends. Members can choose their ideal personal travel dates and incorporate tailored experiences based on their unique interests, while deciding how much day-to-day structure works best for their group. Featured inclusive “just for your special group” amenities and pricing, along with in-destination expert tour guides, private driver ground transportation services, including 4-star accommodations throughout each Cuba adventure itinerary.

A minimum group size of 4-6 (OR) maximum 12-14 people is required for Cuba.

How can I travel to Cuba as a U.S. Citizen?

With decades of political changes, legal travel to Cuba has been a constant challenge for U.S. citizens, making this island of salsa, Colonial architecture and Caribbean beauty a forbidden fruit for the adventurous. Due to THIRDHOME‘s preferred partnership with International Expeditions, who has a reputable history steeped in the support of the Cuban people, the My THIRDHOME Private Cuba Adventure meets all the latest required regulations and is fully compliant in the “Support of the Cuban People”. Guided touring in support of the Cuban people is a required component of each private villa stay, which has been incorporated into the Adventure package. With THIRDHOME‘s established relationship with Cuba and an expert in-destination team, travelers can connect with unique experiences within Cuba’s deeply-rooted culture in an organized small group stay.



  • 3-Bedroom Villa (sleeps up to 6)
  • 5-Bedroom Villa (sleeps up to 10)
  • 7-Bedroom Villa (sleeps up to 14)
  • All bedrooms have private baths
  • All bedrooms lock from the inside
  • All bedrooms have in-room safes
  • Bedding varies in each villa – bedrooms are configured with either King, Queen, or Twin beds
  • All villas are air-conditioned
  • Landscaped gardens and pools
  • Breakfast included each morning
  • Small staff to assist guests


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Welcome to Havana! Meet and greet upon arrival into Havana’s Jose Marti International Airport. You will process through customs and immigrations and retrieve your checked luggage before exiting the airport. Your driver and guide will be waiting just outside the arrivals terminal where they will be holding up a sign with your name on it. If your flight arrives before 2:00 p.m., there will be time to stop for a light bite to eat before proceeding to your private villa for check-in. Upon arrival at your villa, the villa staff will get you settled and welcome you with a refreshing beverage. Your first evening in Havana begins with a visit to the historic Hotel Nacional. Tour the grand lobby and explore the Hall of Havana History and a fascinating collection of memorabilia from the day of crooners and gangsters. Enjoy a famous Mojito in the gardens of the hotel overlooking Havana’s famous Malecon seaside avenue. Your welcome dinner is included tonight at one of the privately owned restaurants, a paladar, which is known for their traditional Cuban cuisine, charming authentic atmosphere and interesting decor. Return to the villa for your overnight accommodations. (Included: Light lunch if arrival is early/Dinner)


Enjoy an early breakfast this morning. Depart the villa with your local guide for an Old Havana exploration (wear comfortable clothing and walking shoes). Stroll leisurely through this remarkable city, visiting the main plazas to experience five centuries of architectural styles and learn how the history of Havana is interwoven with much of North America’s. Listen to romantic tales that create the air of mystique around Cuba and Havana’s notorious reputation. Visit the Almacenes de San Jose artist market for handmade local Cuban crafts; Later, toss your shoes aside and slide into a vintage classic restored car from the 1950’s. Cruise in style with your car, along with a driver guide, through the Malecon and other Havana landmarks and scenic neighborhoods. Enjoy lunch at the newest paladar gem in Old Havana, Paladar 5 Sentidos, where you will taste Cuban fusion cuisine with a European flair. After lunch, enjoy free time this afternoon to explore the city on your own or relax back at your villa. Your guide and driver, along with the in-country concierge team, remain available as required based on however you wish to design the remainder of your day. This evening, experience a special treat without leaving your beautiful villa where you will enjoy your own private Cuban Fiesta with a traditional Cuban dinner, musicians, salsa-lessons and cultural festivities. (Included: Breakfast/Lunch/Dinner)


After breakfast, explore the making of Cuban cigars, a deeply rooted artisan tradition. Visit one of Cuba’s largest cigar factories where a private guide will introduce you to one of the island’s most important exported “artisan” products. You will learn the history and story of how tobacco has been cultivated for the art of rolling cigars, providing a steady source of income for the local people. Afterwards, meet an art curator who will host your exploration into the local Cuban art scene. Visit Bellas Artes (Havana’s fine arts museum) with its extraordinary curated collection of handmade Cuban art pieces. Your art expert will bring the story of Cuba’s society to life through the museums fascinating exhibits. Take a restful break for lunch in the embassy district of Miramar at a lovely paladar in a converted colonial mansion, that serves refined Cuban cuisine with impressive art displays on their walls. Following lunch, unlock the nuances of two Cuban indulgences on an expert-guided rum and cigar pairing experience (referred to locally as a Cuban Maridaje). Continue exploring some of Havana’s small artist studios of the contemporary and up-and-coming artists of Cuba. Return to the villa to relax before dinner. This evening, enjoy a seaside paladar known for their traditional seafood dishes as a delightful dining experience. A driver and guide have been arranged to be available until midnight for everyone who wishes to explore Havana’s nightlife. Return to the villa for your overnight accommodations. (Included: Breakfast/Lunch/Dinner)


Enjoy a leisurely breakfast this morning. After, embark on a delightful music-infused day of Havana! Take a late morning visit to the studio of a noteworthy dance company to experience a rehearsal and engage in a music-filled personal encounter with their dance team. Next, join a crafted cocktails lesson with a master mixologist to learn the nuances of Cuba’s famous rums and their signature cocktails. Nibble on tasty Cuban appetizers as you salute your friends and listen to an award-winning musician performance. Dine at a privately-owned paladar for a light lunch, which is operated by a woman who is locally admired for her authentic tapas-style menu. There is time to relax at the villa in the late afternoon or use your private guide and driver to explore the city further. Dinner this evening is included at a trendy paladar known for their Cuban-Caribbean fusion dishes. Return to your villa for overnight accommodations. (Included: Breakfast/Lunch/Dinner)


After breakfast, depart on a scenic journey just outside Havana to Cojimar, the small seaside town that served as the story backdrop in Ernest Hemingway’s award-winning novel, “The Old Man and The Sea”. Begin an informative walking tour, as your guide reveals the intertwining story of this town, its residents and Papa Hemingway (as the locals refer to him). Enjoy a drink at La Terraza, the bar that was Hemingway’s personal favorite when he would come to town to go fishing aboard his beloved boat, Pilar. Afterwards, roll-up your sleeves and enjoy a hands-on cooking class at a highly cherished local paladar, specializing in one of Cuba’s national dishes, Ajiaco. Enjoy the delicious lunch you have prepared with your friends. Depart after lunch and continue to San Francisco de Paula to visit Hemingway’s former home. Step into his shoes as your expert guide hosts you on a tour of Finca Vigia, revealing interesting memorabilia and stories of the famed writer’s life in Cuba. Return back to Havana, with the remainder of the late afternoon free to discover the culture and sights on your own. As always your driver and guide will remain available as desired. Dinner this evening is reserved at a restaurant that is arguably Cuba’s most renowned and coveted to gain a table at, The Tropicana Cabaret. Reservations are scheduled at 7:00 p.m., so that you have ample time to enjoy dinner and take in the world-famous cabaret show. Please note – there is an additional add-on fee for the addition of the show; refer to pricing below). Return to your villa for overnight accommodations. (Included: Breakfast/Lunch/Dinner)


This morning, relax and enjoy a leisurely breakfast prior to checking out of your villa. The local concierge and in-destination teams will coordinate your airport transfer time approximately 2-1/2 hrs prior to your flight departure. Transfer to airport for check-in of your return flight home.

What’s Included

  • English-speaking expert tour director
  • Private services of an in-country Cuba concierge team 24/7
  • 5 nights boutique accommodations in private villas – your choice of villa size
  • Arrival meet and greet at airport with private transfers to your villa and departure transfers
  • Private professional English-speaking guide and driver, along with bottled water stocked in the vehicle
  • All guided activities, entrance fees and touring as outlined in itinerary
  • All meals as outlined per day in itinerary
  • Two domestic drinks (bottled waters, sodas, domestic beer) per person with meals when dining at historic paladares as outlined in itinerary
  • Tips for guides during included activities as outlined in itinerary
  • Tips for waiters/restaurant staff when dining at historic paladares in itinerary
  • Usage of one local mobile phone while in Cuba is loaned to the group host to use as needed. The cell phone will be preloaded with limited funds credit and pre-programmed with concierge and guide’s phone numbers to stay in contact during the stay.

What’s Not Included

  • Mandatory Cuba Tourist Entrance Visa – approximately $100 USD per person
  • International Roundtrip Airfare – guests can arrange own flights or inquire with our team
  • Gratuities for guide and driver (approximately $20 Cuban Currency per day/per guest)
  • Meals not mentioned in the above inclusions
  • Porterage/luggage handling tips as desired
  • Optional personal activities or items not mentioned in the above inclusions
  • Optional Rum and Cigar Tasting: $85 per person USD – includes a flight tasting series of rare small-batch premium Cuban Rums not found in the USA, being paired with authentic Cuban rolled artisan cigars
  • Optional Cuban Cabaret Tropicana Club Show: $220 per person USD – includes Classic Car ride roundtrip form villa to dinner/show, VIP private table with preferred level show tickets, a bottle of rum and tips
  • IMPORTANT NOTE: Cuba does not offer the traveler convenience of utilizing US-bank issued credit cards nor are there ATMs where you can withdraw USD or local currency. As such, Cuba travelers need to be prepared to bring cash. We recommend approximately $200 USD per person/per day for out-of-pocket expenses and small purchases. Should the need arise to exchange money in Cuba, your guides can assist.

Passport & Visa Requirements

Adventure Pricing


3-BEDROOM VILLA: $4695 per person (sleeps 6 people)

5-BEDROOM VILLA: $4595 per person (sleeps 10 people)

7-BEDROOM VILLA: $4495 per person (sleeps 14 people)


$750 per person deposit based on 3-Bedroom Villa

$850 per person deposit based on 5-Bedroom Villa

$950 per person deposit based on 7-Bedroom Villa

Final payments are required 60-days prior to your departure

Deposits & Final Payments are non-refundable for all My Private Adventures

All My Private Cuba Adventures require a minimum advance notice of 90-days or more


Rates are subject to change if traveling after 2020, or during the Christmas/New Year holiday season between December 15th thru January 5th. Adventure package cost could vary slightly depending on the exact final number of guests. International Expeditions reserves the right for slight day-to-day itinerary modifications to this small-group private Adventure program due to Cuba logistics and in-destination ground operations. Adventure packages are 100% non-refundable after final payment. THIRDHOME strongly recommends the purchase of travel insurance. Click here to view the THIRDHOME Adventures Terms and Conditions.


Recently our family went to Cuba privately with all arrangements having been made by THIRDHOME Custom Travel & Adventures – Liz Bates. To begin with, after traveling much of the world with very good assistance, nothing compares with the virtually perfect arrangements we experienced through Liz’s efforts.  Words alone cannot that capture Havana….dreamscape, romantic, a paradise rising from a falling phoenix.  None of these words really do justice to the extraordinary beauty and the bone-deep rhythm of this place.  The best part of the trip was the Cuban people, how they can keep moving on despite the embargo in place. It has changed me and I already look forward to returning one day. While in Cuba we met important artists and museum directors and visited amazing galleries. We traveled in restored 1950’s classic cars and, on long trips, had the best transportation available.  Our local expert Cuban guide was incredibly knowledgeable and made sure we saw everything possible in the 6 days we toured around together.  Another huge highlight included (which is a must-do experience) is a visit to the Tropicana Club.  Cuba was amazing and seems to be coming into its own. The people are gentle, kind and interesting; and all of the traditional paradar private restaurants that we had access to through Liz’s expertise were so much better than we expected. Liz took the time to learn all of the important factors about us as a family and individually created a visit to Cuba that was meaningful from beginning to end. The private villa we stayed in was superb and staffed by the most wonderful Cuban people.  Our villa was the perfect oasis to rest in after being active all day, the art and the staff especially very special. Havana is fabulous – every need and day was met beyond our expectations.  Our recommendation: Call Liz and get to Cuba now! 

Robert & Laura K.

Cuba was an incredible destination – it was definitely something we wouldn’t have pulled off on our own. The itinerary was fabulous and everything was amazing – a beautiful tasting of art, culture and the people – everything was so rewarding! 

Susan C.

The trip was fabulous, it exceeded all of our expectations!!! It was so well run, and everyone from the villa staff, guides and special guests were wonderful. 

Marilyn and John C.

Want to read more reviews? Click here to visit the Adventure page for Mariel Hemingway’s Hidden Havana, a small-group tour that THIRDHOME members recently returned from.

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