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.