Arrive in Havana and meet your guide at the airport. Receive a brief introduction before heading out to explore Havana in an iconic classic car that is used several times throughout your trip. Your first destination is La Bodeguita del Medio, a famous "little bar in the middle of the block" decorated with autographs and photographs of its guests. Enjoy lunch and perhaps sample a "Double Papa", a double rum drink tribute to Ernest Hemingway. Other famous former patrons of the bar include Joe DiMaggio, Nat "King" Cole, Frank Sinatra, Marilyn Monroe, Francis Ford Copolla, Pablo Neruda, and Benny Moré.

After lunch set out on a walking tour of Habana Vieja's historic district and the Havana Club Museum of Rum. Learn about the rum-making process, from the sugar cane mill to the copper shop where casks are made to the tasting room. Stop in at another of Hemingway's favorite bars, El Floridita, where his corner seat is forever chained off. It was here that he conceived the inspiration and wrote his novel For Whom the Bell Tolls. Ava Gardner, Tennessee Williams, Spencer Tracy, Jean-Paul Sartre, and Gary Cooper visited here as well.

Tonight get a taste of Havana's nightlife at the legendary Tropicana club. View a spectacular Cabaret show in the open air under Havana's night sky, set amidst tropical forest with large trees. This world-class entertainment survived the Cuban Revolution and dates back to the club's glory years in the 1950s. Enjoy the salsa music and the rhythms and costumes of the dancers as they pay tribute to Cuban and African heritage. 

Continue exploring Hemingway's Cuba with a visit to his former estate at Finca Vigia, where he wrote nine novels, and the Museo de Ernest Hemingway. After touring his home and the estate grounds head to the small fishing town of Cojimar, inspiration for The Old Man and the Sea. Hemingway and his boat Pilar were frequent visitors to this town. Explore Cojimar before lunch at the El Ajiaco restaurant, where you receive a lesson in how to make an amazing mojito using herbs from the property's gardens.

After lunch transfer back to Havana to visit a vintage car restoration garage which brings classic cars back to their original comfort and elegance. Next it's off to tour one of Cuba's oldest cigar factories, where you can view the modern production process in a historic building. Following your tour head to Miramar to visit La Casa del Habano, one of Cuba's finest cigar stores. Tour the store while sampling Cuban coffee served on tobacco leaves. Return to your hotel for a brief rest.

Tonight enjoy dinner at a local paladar before heading to the Fábrica de Arte Cubana, a former cooking oil plant transformed into one of Havana's premier nightclubs and cultural centers with multiple performance venues and art galleries. Experience this innovative and lively community project before returning to your overnight accommodations.

After an early breakfast hop into a classic car for your journey west toward Pinar del Rio and the province's tobacco mecca, Vuelta Abajo. Arrive at the world's most renowned farm for growing cigar tobacco, Finca del Pinar Robaina. The founder, Alejandro Robaina, is considered "The Godfather" in the Cuban cigar business. Enjoy a personal tour of the farm and see the phases of production before lunch at the plantation cafe.

Depart for the town of Pinar del Rio and check into your classic hotel with Spanish colonial architecture. Embark on a walking tour and visit a liqueur factory to sample a local specialty, Guayabita del Pinar. Made from the tiny guava berries (guayabitas) of a local plant and infused with sugarcane liquor, Guayabita del Pinar is a rare treat that is produced locally in limited quantities.

Next tour the Francisco Donatien Cigar Factory, a former prison that now employs 50+ cigar rollers who hand-roll Trinidad and Romeo y Julietas brand cigars. As you observe the process your appreciation is enhanced of the pride taken in the trade. Cross the street to the Casa del Tobacco, where you can purchase cigars and view historic cigar posters. Tonight's dinner is at a local paladar.

Spend the day in Valle de Viñales, a UNESCO World Heritage Site in the Sierra de los Organos mountains. The valley is a karstic depression enriched by steep limestone cliffs, or "mogotes". Eroded away by rain, these outrcrops rise as high as 300 meters and stand in stark contrast to the flat plain of the valley. A cave system dots the surrounding hillsides, complete with underground pools, vegetation, stalactites and stalagmites, and evidence of historical use by the indigenous Guanahatabeys. Viñales Valley is also significant for its historical and cultural importance, as it maintains traditional methods of agriculture and has preserved its colonial architecture, crafts, and music. Hike along the valley's sprawling trails, explore the underground caves, and observe vast tobacco fields. Lunch is at a nearby organic farm, where you can meet with the farmers, learn about organic agriculture in Cuba, and sample fresh produce.

Cruise back to Havana in a classic car and head to the Mercado San José, where you can peruse the colorful stalls of handcrafted goods and cheerful vendors. Located in an old warehouse on Havana harbor, the market also features art exhibitions and theatrical performances among its authentic souvenirs.

Celebrate your final evening together in Cuba with a farewell dinner featuring the best of Cuban dishes.

Depending on your flight schedule, you may visit the Museum of Fine Arts (Museo Nacional de Bellas Artes de La Habana) in central Havana this morning. The museum is comprised of two buildings of collections: one dedicated to 17th century - contemporary Cuban art and the other to European art including originals by Goya, Murillo, Velasquez, Gainsborough, Rubens, and various impressionists as well as ancient Egyptian, Roman, and Greek art.

Transfer to the airport to catch your return flight home.