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5 days


We invite you to experience Cuba’s indulgent side, its glamorous side, its uninhibited side. The side that enticed legends to its shores and then created them.

Step into Cuba’s most illustrious bars, drive around in timeless classic cars that take you back to another era, and indulge your senses with Cuba’s puros and libations. Follow in the footsteps of Hemingway, Sinatra, Gary Cooper, and Tennessee Williams. Sit in the Tropicana and imagine Nat “King” Cole singing into the hot Havana night. Sip on a daiquiri and see where Hemingway toiled away at his novels. Wander through tobacco farms where the world’s best cigars are produced and made – and then sit down and enjoy one.

Experience classic, classy Cuba on our new Classic Cars, Rum, and Cigars tour. Don’t just read Cuba’s story – live it. Live it while learning richly from this Educational Exchange program, flooded with the knowledge of our teachers – cigar aficionados, rum connoisseurs and classic car enthusiasts. Designed for small groups of two to six people, and perfect for a private journey, this tour dives deep into Cuba’s history and pleasures.

*Note: this tour is available with TWO accommodation options:

  • Traditional Casa Particularesor


  • High-end Casa Particulares. Casas Particulares are private home accommodations similar to B&Bs in the United States, though some high-end casas can feel more like a boutique hotel than guest home.

This itinerary is available as a fully legal People-to-People tour for US citizens if booked through Natural Wonders Tours.


Day 1

Arrive Havana

Our tour leader will greet you at the Havana Airport and provide a brief orientation before you head out into Cuba’s most dynamic city. You’re picked up in Cuba’s iconic classic cars that will serve as your transportation for part of your trip. Go to La Bodeguita del Medio, then lunch. Walking tour of Old Havana, visit Museum of Rum.

Check in to casa, then dinner at a Havana paladar. Either before or after dinner, we’ll stop by another of Hemingway’s illustrious watering holes: El Floridita.

We finish off our day with a trip to the legendary Tropicana before we return by taxi to our accommodations for the evening.

Accommodations: Havana Casa particular

Meals Included: L,D


Day 2

Cojimar, Ernest Hemingway Museum, and Fábrica de Arte

It’s a short drive east to the small fishing town of Cojimar where we walk through the town and stop at some of Hemingway’s favorite sundowner spots before joining our friends at El Ajiaco restaurant.  We visit the gardens where some of their vegetables and herbs are grown, then have a lesson in how to make a stunning mojito.  Then lunch.

Go to Finca Vigía and the recently renovated Museo de Ernest Hemingway. After our tour, we return to Havana to visit a vintage car restoration garage. The garage brings nostalgia-laden classic cars back to their original comfort and elegance so that all guests can have the opportunity to travel back in time.

We let the classic cars rest for the night and use regular Cuban taxi’s for an authentic experience. We pick you up from your accommodations and we are off to enjoy an authentic Cuban meal at one of Havana’s finest paladars before hitting the town for a night out. While the Tropicana might be Havana’s most iconic nightclub, the Fábrica de Arte Cubano is its most entrepreneurial.

Accommodations: Havana Casa Particular

Meals Included: B,L,D


Day 3

Valley de Viñales and Pinar del Rio

Drive west to Valley de Viñales. Surrounded by the pine-clad hills of the Sierra de los Órganos, Valley de Viñales is a fantastical sprawl of lush green grass and limestone mogotes that rise precipitously from the hallowed ground.  We explore the hidden sights of the valley flecked with tobacco farms before we head to a nearby organic farm for lunch. Meet with the people who tend the land, learn about organic agriculture in Cuba and sample their fresh, carefully cultivated produce.  We spend more time in the afternoon exploring the valley’s beauty.  Later in the day we head to the nearby provincial capitol of Pinar del Rio and check into our casa.  We dine at one of the city’s fine Paladars.

Accommodations: Pinar del Rio Casa Particular

Meals Included: B,L,D


Day 4

Pinar del Rio Town; Finca del Pinar Robaina, Return to Havana

After breakfast, we enjoy a walking tour of the town of Pinar del Rio. We visit the Francisco Donatién Cigar Factory, housed in a former prison that was repurposed in the 1960s. If time and interest, we then saunter over to the Casa del Tobacco, near the Francisco Donatién Cigar Factory.

Cuba may be famous for its rum apéritifs, but locals have another favorite: Guayabita del Pinar. Growing in the Pinar del Río province is a plant with tiny guava berries called guayabitas. Infusing guayabita flavor with sugarcane liquor produced the Guayabita del Pinar liqueur, with dry and sweet varieties. Produced locally and limited in production, it’s a definite treat even more special for its rarity. There is also opportunity, if desired, to explore other historic sites in the city.

From Pinar del Rio city, we head out to go see the source for the actual tobacco leaves.  We drive to into the countryside, to Finca del Pinar Robaina, whose founder, Alejandro Robaina, was considered “The Godfather” in the Cuban cigar business. Enjoy a lively, informative and personal tour of the farm, educational at heart, and marvel at the brilliant green panorama of tobacco plants plotted in neat rows, rustling in the wind. We get to see the phases of production before sitting down at the plantation café for a delicious lunch and indulging in the creamy aroma of puros that saturates the air.

Our adventure continues as we cruise back to Havana and enjoy the panorama on the way. We return to Habana Vieja’s cobbled streets and head to the Mercado San José.

We celebrate our final evening together in Cuba with a farewell dinner that features the best of Cuban dishes. Take a page from Hemingway’s book and sit down with a mojito or daiquiri Papa Hemingway style.

Accommodations: Havana Casas Particular

Meals Included: B,L,D


Day 5

Museum of Fine Arts and Adios Havana!

If flight schedule allows time this morning, we visit the Museum of Fine Arts in central Havana (Museo Nacional de Bellas Artes de La Habana).  You also have the option of traveling to Miramar to visit La Casa del Habano—considered one of Cuba’s finest cigar stores. Tour the picturesque store and hopefully get a chance to talk to Carlos Robaina, son of Cuba’s Godfather of cigars. Sip on a Cuban coffee served on tobacco leaves while trying out some aromatic products before heading to the airport.

Once done, we make our way to the airport to catch your return flight home.  Today’s transport is done by regular taxi.

Meals Included: B

Small Group Tours for 2-6 People, Support for the Cuban People

Prices include:

  • Experienced English-speaking guide(s)
  • Private pre-tour orientation meeting
  • Cuba Unbound hand-crafted itineraries including: carefully chosen people-to-people/support for the Cuban people activities, personal visits and presentations with experts in a variety of fields and topics, and access to exclusive experiences
  • Accommodations as noted in the itinerary
  • All meals as noted in itinerary
  • Certification of travel to Cuba under the U.S. Department of Treasury general license
  • Small group size: 2-6 guests
  • All entrance fees to include events and activities
  • Classic 1950’s American car transportation and regular taxi transport as indicated
  • Clean drinking water available at all times
  • Gratuities for specialized guides and presenters, luggage handling, restaurant staff, and activities throughout tour

Prices do not include:

  • Round-trip flight from US to Havana
  • Cuba Tourist Visa Fee
  • Guide gratuities (all gratuities for servers, and others who help us during our tour are included)
  • Personal expenses such as souvenirs, gifts, alcoholic drinks, additional drinks, entertainment fees not listed in itinerary, and incidentals.
Old red Car in Cuba
green boat in water
crabs on a beach
Cuba Travel Photo blue car
Cuba Travel Photo street
Cuba Travel Photo
Cuba Travel Photo
walking on peer green boat
Old red Car in Cuba
man playing guitar
man and woman thumbs up
people in Cuban forest
Cuban sea food
riding bikes in Cuba
people enjoying coffee
Cuban market
Cuban busy street lights
piano in Cuba
Cuban town roof top
Cuban town
Cuban man

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