1 Week in Cuba: Cars, Cigars, and Cabarets

Cuba is a mother lode for anyone who loves classic American autos, fine cigars, quality rums, and Las Vegas-style cabaret revues. Before 1959, Havana was the hottest spot in the Caribbean, notorious for its glittering cabarets, smooth rum, and chrome-laden Cadillacs. The good news is that the tail fins of ’57 Eldorados still glint beneath the floodlit mango trees of nightclubs such as the Tropicana, the open-air extravaganza now in its seventh decade of stiletto-heeled hedonism.

Day 1

Arrive at José Martí International Airport in Havana; transfer to a hotel or casa particular in Habana Vieja or Vedado.

blue car driving in front of the capitol building in Havana Cuba
Rent a classic car and take it for a spin on a tour through Havana. Photo © clamon/iStock.

Day 2

This morning, concentrate your time around Parque Central, where the highlight will be the shop at Fábrica de Tabaco Partagás. After buying some premium smokes, head to the Fábrica de Tabaco H. Upmann (formerly Romeo y Julieta) for a guided tour of this cigar factory. Then rent a classic 1950s auto and set out for a tour of the city. In the evening, enjoy dinner at La Guarida restaurant and then thrill to the sexy spectacle of the Hotel Nacional’s Cabaret Parisien.

Day 3

Today, follow Hemingway’s ghost. Drive out to the village of San Miguel del Padrón and the Museo Ernest Hemingway, in the author’s former home. Afterwards, head to Cojímar for a seafood lunch at La Terraza restaurant, once popular with Papa and his former skipper, the late local resident Gregorio Fuentes. Return to Havana for a mojito and stogie at La Bodeguita del Medio. Explore Plaza de la Catedral and Plaza de Armas, being sure to stop in at the Hotel Ambos Mundos (Room 511, where Hemingway was a longtime guest, is a museum) and the Museo del Ron, a splendid museum giving insight into production of Cuba’s fine rums. This evening, sample the daiquiris at El Floridita.

aerial view of tobacco farmland in Cuba
Visit the tobacco fields in Valle de Viñales. Photo © venemama/iStock.

Day 4

Rent a car or hire a taxi for a day trip to Pinar del Río. Set out early to visit the tobacco fields of Valle de Viñales and the Finca El Pinar San Luis, finca (farm) of the late Alejandro Robaina, a legend after whom the Cuban state named a brand of cigar. Return to Havana in the evening for dinner at El Aljibe. Share fine cigars and añejo rums with the connoisseurs at the La Casa del Habano in Miramar.

Day 5

Head out to Marina Hemingway for a full day of sportfishing for blue marlin in Hemingway’s “great blue river.” This evening, enjoy dinner at La Fontana, one of Havana’s choicest restaurants.

Fábrica El Laguito cigar factory in Havana, Cuba.
Fábrica El Laguito. Photo © Christopher P. Baker.

Days 6-7

This morning, head to Club Habana, a chic private club (open to nonmembers for a fee) where you can relax on the fine beach, partake of water sports, and sample cocktails and fine cigars. After dinner at El Cocinero paladar, head to the Tropicana nightclub for the sauciest cabaret in Cuba.

Related Travel Guide

Pin For Later

cuba itinerary pinterest graphic