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 paganism. OK, big spender, let the fun begin.
This morning concentrate your time around Parque Central , where the highlight will be a guided tour of the Fábrica de Tabaco Partagás . After buying some premium smokes, head to either the earthy art deco bar in the Edificio Bacardí  or the sophisticated bar in the Hotel NH Parque Central  to enjoy your stogie with a Cuba libre. Then rent a classic 1950s auto from Gran Car and set out for a tour of the city.
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 long-time guest, is a museum) and the Museo de Ron , a splendid museum giving insight into production of Cuba’s fine rums. This evening, sample the daiquiris at El Floridita .
Rent a car (pick it up the day befiore if possible), 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 of the late Alejandro Robaina, a legend after whom the Cuban state named a brand of cigar.
Head out to Marina Hemingway for a full day sportfishing for blue marlin in Hemingway’s “great blue river.” This evening, enjoy dinner at one of Havana’s chicest restaurants. If you still have energy after a day battling game fish, sample the retro nightlife at the Café Concierto Gato Tuerto nightclub .
This morning head to Club Habana, a private and very chic members 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 Cocina de Lilliam  paladar, head to the Tropicana  nightclub for the sauciest cabaret in Cuba. In the morning, transfer to the airport for your departure flight.