Cuba’s story is like many stories - composed of shadows and light, sombras y luz. A study in chiaroscuro. Repression and revolution. Dilapidated plazas next to opulent palaces. The silhouette of cigar smoke drifting across the luminous shimmer of the Tropicana Cabaret. The beauty is in the contrast; the temptation in the unpredictability.
Even though it’s been half a century since the glamourous days when Hollywood flew down in droves for weekends of dissipation and decadence, Cuba retains the air of flash and magnetism. Stepping into Havana can be like stepping into a self-indulgent novel or one of Frank Sinatra’s film sets. 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: 1) Traditional Casa Particulares or 2) 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 accommodation than guesthouse.
Images & Videos
Havana Hotspots La Bodeguita del Medio, El Floridita, and Tropicana
“My mojito in La Bodeguita, My daiquiri in El Floridita”—Ernest Hemingway
This tour begins when you arrive at the airport, where your local guide and driver will greet you 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. Roll down the windows, smell the mimosa sifting through the air, and hear the rumble of engines as we make our way to La Bodeguita del Medio.
La Bodeguita del Medio may translate to the unassuming name of “the little bar in the middle of the block,” but the restaurant and bar is anything but bland. La Bodeguita’s claim to fame lies in being one of Hemingway’s endorsed haunts where he discovered the mojito. The bar now serves double rum portions for the “Double Papa”—Hemingway’s specialty serving that leaves little doubt for the writer’s love of rum. Although the restaurant has a framed piece of parchment blazoned with Hemingway’s seal of approval and signature, stepping into La Bodeguita means you’ll be swilling some rum where Hemingway wasn’t the only famous patron. Joe DiMaggio, Nat “King” Cole, Frank Sinatra, Marilyn Monroe, Francis Ford Copolla, Pablo Neruda, and Benny Moré also found their way here. The bar’s walls are slathered in autographs, centerfolds, and photographs—some from illustrious guests and some from simple passersby who want to make their mark.
After lunch and possibly a Double Papa, we stretch our legs with a walking tour of Habana Vieja. Colonial Havana’s colonnaded streets are as colorful as our cars. As you walk through a rainbow of pastels listen for rumba riffs rumbling down the cobbled streets and the sounds of people working behind walls of mystery. Our walking tour takes us to Habana Vieja’s historic district and the Havana Club Museum of Rum, which offers a real-time journey through the rum-making process—from the sugar-cane mill to the cooper shop where the aging casks are made to the tasting room. We may also drop into Sloppy Joe’s, another favorite watering hole of Hemingway and recently restored to its former glory.
We will head to you accommodations for the night so that you can rest and prepare for a night out in the city.
We pick you up in your classic car (or regular taxi if not available) and head out to one of Havana’s Paladares for a tasty dinner. Either before or after dinner, we’ll stop by another of Hemingway’s illustrious watering holes: El Floridita. Hemingway sat in a corner seat, drank daiquiris, and conceived then wrote For Whom the Bell Tolls there. Hemingway must have been a trend setter because the bar also saw visits from Ava Gardner, Tennessee Williams, Spencer Tracy, Jean-Paul Sartre, and Gary Cooper. Papa Hemingway remains their favorite, and his seat remains forever unoccupied and chained off. Hemingway drank here a lot and drank a lot here. Have a daiquiri and see if you feel some literary inspiration yourself.
We finish off our day of literature and libations with a trip to the legendary Tropicana. Set in the open Cuban sky, the decant night-club has retained the glamour and glitz over the years. Salsa shows and señorita showgirls survived the revolution and continue to set nights ablaze. Enjoy the performance and Havana’s most notorious nightlife spot before we return by taxi to our accommodations for the evening.
Cojimar, Ernest Hemingway Museum, and Fábrica de Arte
Your guide picks you up in your Classic Car after breakfast to begin our day of all things Hemingway. It’s a short drive east to the small fishing town of Cojimar, which inspired The Old Man and the Sea and saw frequent visits of Hemingway and his boat, Pilar. We walk through the town and stop at some of his 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. With our minds ablaze and stomachs prepped, we sit down for the best lunch in Cojimar.
After lunch, we continue our exploration of Papa Hemingway’s Cuba as we make our way to his former estate at Finca Vigía and the recently renovated Museo de Ernest Hemingway. Hemingway lived in the Moorish-style home with his third wife, Martha Gellhorn, and wrote nine novels within its walls. Wander the rooms and the grounds of the estate and see where Hemingway lived his life as a man while writing novels that made him a legend.
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 return to our accommodations for a brief rest and for a chance to prepare for another fun-filled night in Havana.
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. Not just a nightclub, Fábrica de Arte teems with artists and musicians who don’t simply entertain but press the boundaries of Cuban culture. Take in the sights, mix and converse with the locals, and move to the beat in this stunning performance space before returning to our accommodations for the evening.
Valley de Viñales and Pinar del Rio
Boisterous Havana recedes into the bucolic countryside as we drive west in classic style, into one of Cuba’s most stunning landscapes: 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. A maze of caves curve through the mountains and defined paths are a rare luxury in Cuba’s create-your-own-adventure playground. 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 capital of Pinar del Rio and check into our classic hotel with Spanish Colonial architecture or another option. We dine at one of the city's fine Paladars.
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. Not a huge factory, there are 58 cigar rollers who artfully hand-roll cigars of the Trinidad brand, as well as Romeo y Julietas. The workers appreciate our visit, with obvious pride in their pride in their work as we learn a bit of their lives and trade. If time and interest, we then saunter over to the Casa del Tobacco, near the Francisco Donatién Cigar Factory. The store has a number of historic cigar posters that show the long tradition of this economically and culturally important industry in Cuba.
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. It even has its own song—Cuban musician Cándido Fabré’s “Guayabita del Pinar” that you can appreciate as you sample the Cuban delicacy. 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. The Godfather developed the farm that is now the world’s most renowned plot for growing cigar tobacco. 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. It’s the only tobacco zone which grows all types of leaf—wrappers, fillers, and binders—and 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 in style to Havana and enjoy the panorama on the way. We return to Habana Vieja’s cobbled streets and head to the Mercado San José. This crafts fair has a palpable soul with its handcrafted goods, colorful stalls, and cheerful vendors. It also features theatrical performances and art exhibitions—transforming the space from a market to a cultural center. It’s the perfect place to visit on our last full day on the island if you’re hoping to take a piece of Cuba with you!
After we drop off our souvenirs at our accommodations, 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.
Museum of Fine Arts and Adios Havana!
, and as required by U.S. law, we have a full-time agenda of people-to-people activities. Cuba has it’s own beat and things don’t always run on time. The activities and visits listed are not guaranteed but we endeavor to do our best to provide the content intent of this people–to-people program. Visiting developing countries can be eye-opening and life-changing, and hopefully visiting Cuba is both. Accommodations may not be up to the standards you are used to. Sometimes the hot water or air conditioning doesn’t work. We ask all our guests to appreciate the authenticity of your cultural encounters as well as the people, food, culture, and adventures that are exceptional in their difference. Our local guide, along with your Cuba Unbound Tour Leader promise to do their best to make this a fascinating and educational experience.
Dates & Rates
Rates (all prices below are per person in USD)
Standard Casas Particulares:
- 2 guests (1 car) - $2,245
- 3 guests (1 car) - $2,045
- 4 guests (2 cars) - $2,145
- 5 guests (2 cars) - $1,945
- 6 guests (2 cars) - $1,845
- 6 guests (3 cars) - $2,045
High End Casas Particulares:
- Please inquire for specific pricing.
Dates: Trips depart daily on demand
Group Size: This trip is perfect for one or two couples traveling in one car, but we can group several cars together if you have a larger group. Because you will also have a guide and a driver with you, two couples per car is the absolute maximum and you would likely be more comfortable with just one couple per car.
• Experienced English-speaking guide(s)
• Specialized activity guides based on activity of trip (kayaking, biking, hiking, etc.)
• Specialized equipment needed for activities such as kayaks, bikes, helmets, paddles, personal flotation devices, etc.
• Private pre-tour orientation meeting
• Cuba Unbound hand-crafted itineraries
• 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 (Custom tours for 2, group tours are 16-18)
• All entrance fees to include events and activities
• All in-country ground transportation
• Clean drinking water available at all times
• Gratuities for presenters, luggage handling, and restaurant staff
• Round-trip air to/from Cuba
• Cuba Tourist Visa Fee (ranges from $50-$100 depending on where you buy it)
• Guide and driver gratuities
• Personal expenses such as souvenirs, gifts, alcoholic beverages, additional entertainment outside the standard itinerary, and incidentals
FAQ & More
This is something you'll hear in Cuba a lot. A casa particular is a private accommodation or private homestay in Cuba, very similar to a bed and breakfast, although it can also take the form of vacation rental. On ROW's Cuba Unbound tours, you can expect to stay in a mix of casas particulares, making for a full and authentic visit to Cuba.
This tour is designed for a small group of 2-6 people. While we can accommodate a solo traveler, we unfortunately must charge the double occupancy rate.
Yes! US visitors can legally bring back $100 worth of Cuban cigars (or rum). Note that it is still illegal to smoke the cigars in the US, but US citizens may smoke them in other countries.
For Cuban cigar pricing info, check out Cigar Aficionado
Yes! However, the total worth of rum cannot exceed $100, which is the total amount allowed for rum and cigars combined.
There will be some free time between tours and meals.