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 on how to make a stunning mojito. With your mind ablaze and your 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.

Havana's vibrant atmosphere gives way to the serene countryside as you travel west in a classic car to the stunning Vinales Valley. This landscape is a lush expanse of green fields dotted with dramatic limestone mogotes and framed by the pine-covered hills of the Sierra de los Organos.

Explore the valley's hidden gems, where tobacco farms are scattered across the fields, and winding caves carve through the mountains. Stop at a nearby organic farm to meet the farmers, learn about sustainable agriculture in Cuba, and sample freshly grown produce.

Later, visit a local facility where tobacco leaves undergo processing before being sent to aging and cigar factories. The day concludes with dinner at a local Paladar, offering a taste of Viñales' authentic flavors, before settling into your accommodations for the night.

After breakfast, set out for a scenic cruise to Havana, taking in the views along the way. Explore the cobbled streets of Habana Vieja and visit the vibrant Mercado San Jose. This bustling market offers handcrafted goods, colorful stalls, and lively performances, making it a cultural hub. It’s an ideal stop for picking up any final souvenirs.

After dropping off your souvenirs at your accommodations, enjoy a farewell dinner featuring classic Cuban dishes. Sip a mojito or a daiquiri Papa Hemingway style to celebrate the final evening in Cuba.

If the schedule permits, start the day with a visit to Havana's Museum of Fine Arts (Museo Nacional de Bellas Artes de La Habana). Explore two remarkable buildings: one dedicated to Cuban art, showcasing diverse subjects and styles, and the other featuring a European masters collection, with originals by Goya, Murillo, Velasquez, Gainsborough, Rubens, and various Impressionists. The museum also holds one of Latin America's most important Greek and Roman art collections.

Alternatively, head to Miramar for a visit to La Casa del Habano, one of Cuba’s premier cigar stores. Tour the picturesque shop, meet Carlos Robaina, son of Cuba’s "Godfather of cigars," and enjoy a Cuban coffee served on tobacco leaves while sampling aromatic products before heading to the airport.