Arrive at the airport, where your local guide and drivers greet you and provide a brief orientation before you head out into Cuba’s most dynamic city. Your first stop: La Bodeguita del Medio, which translates to the unassuming name of “the little bar in the middle of the block,” but the restaurant and bar are anything but bland. La Bodeguita’s claim to fame lies in being one of Hemingway’s endorsed haunts where he discovers 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 swill 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 find 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 this welcoming cocktail, stretch your legs with a walking tour of Habana Vieja, stopping in the area for lunch. Colonial Havana’s colonnaded streets are as colorful as our cars. Walk through a rainbow of pastels to the Havana Club Rum Museum, where you enjoy a guided tour to learn about the manufacturing process from field to bottle.

Head to your accommodations for the night so that you can rest and prepare for a night out in the city.

You'll be picked up in your classic car (or regular taxi if not available) and head out to one of Havana’s Paladares for a tasty dinner. Before or after dinner, stop by another of Hemingway’s illustrious watering holes: El Floridita. Hemingway sits in a corner seat, drinks daiquiris, and conceives then writes For Whom the Bell Tolls there. Hemingway must have been a trendsetter because the bar also sees 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 drinks a lot and drinks a lot here. Have a daiquiri and see if you feel some literary inspiration yourself.

Finish off your day of literature and libations with a trip to the legendary Tropicana. Set in the open Cuban sky, the decadent night-club has retained the glamour and glitz over the years. Salsa shows and señorita showgirls survive the revolution and continue to set nights ablaze. Enjoy the performance and Havana’s most notorious nightlife spot before returning by taxi to your accommodations for the evening.

Your guide picks you up in your Classic Car after breakfast to begin your 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. You walk through the town and stop at some of his favorite sundowner spots before joining your friends at El Ajiaco restaurant. Visit the gardens where some of their vegetables and herbs are grown, then have a lesson in how to make a stunning mojito. With your mind ablaze and stomach prepped, you sit down for the best lunch in Cojimar.

After lunch, you continue your exploration of Papa Hemingway’s Cuba as you make your 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 your tour, you 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.

You return to your accommodations for a brief rest and for a chance to prepare for another fun-filled night in Havana.

The classic cars rest for the night, and regular Cuban taxis are used for an authentic experience. You are picked up from your accommodations, and you 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 your accommodations for the evening.

Boisterous Havana recedes into the bucolic countryside as you 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 curves through the mountains, and defined paths are a rare luxury in Cuba’s create-your-own-adventure playground. Explore the hidden sights of the valley flecked with tobacco farms before heading 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. After visiting the valley and learning about how the tobacco farmers (vegueros) grow and process their production, in the afternoon, you will drive through town to visit a plant where the tobacco leaves bought by the government go through a bigger scale industrial process before being sent to aging and then to the Cigar Factories.

Head to your accommodations for the night and dine at one of the town's fine Paladars.

After breakfast, your adventure continues as you cruise in style to Havana and enjoy the panorama on the way. 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 your last full day on the island if you’re hoping to take a piece of Cuba with you!

After dropping off your souvenirs at your accommodations, celebrate your 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.

If the flight schedule allows time this morning, you can visit the Museum of Fine Arts in central Havana (Museo Nacional de Bellas Artes de La Habana). This fabulous museum has two impressive buildings. One is dedicated to Cuban art and includes a wide range of subjects and styles. The other is a divine European masters collection, including originals by Goya, Murillo, Velasquez, Gainsborough, Rubens, and various impressionists. The museum also houses one of the most important collections of Greek and Roman art in Latin America.

Alternatively, you 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, make your way to the airport to catch your return flight home. Today’s transport is done by regular taxi. As required by U.S. law, there is a full-time agenda of people-to-people activities. Cuba has its own beat, and things don’t always run on time. The activities and visits listed are not guaranteed, but efforts will be made 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. Guests are asked to appreciate the authenticity of cultural encounters as well as the people, food, culture, and adventures that are exceptional in their difference. The local guide, along with the Cuba Unbound Tour Leader, promises to do their best to make this a fascinating and educational experience.