Cubans could write the book on sensual pleasures… and none define Cuba more than Cuban cigars and cabarets. Better yet, imagine smoking a stogie while riding in a classic convertible auto to a night of nocturnal bliss at the Tropicana… a 1939-birthed salsa-driven extravaganza recalling Havana’s halcyon heyday of sin. Don’t believe anyone who tells you that Cuban communism means Soviet-style dull.
Cuba is easily the biggest classic American automobile museum in the world, and the streets of every city a paean to re-revolutionary retro Detroit. Sure, most resemble automotive Frankenstein’s monsters, with all manner of Soviet and other non-original bits—even tractor or boat engines—stitched onto the original body and frame. But there’s no shortage of pristine-looking Cadillacs and Chevrolet Impalas with fins sharp enough to draw blood. They await at your service to ferry you as desire.
You could build an entire week (or longer) itinerary around such indulgence. So, to make your life easy, here’s a 4 day itinerary to get you started.
OK, so you’ve arrived Havana. Start as you mean to continue by hiring a private convertible 1950s classic car at Parque Central—ground zero for the best Detroit dowagers of yesteryear. Your afternoon tour should include the main highlight attractions, being sure to include Plaza de la Revolución, Parque Histórico-Militar El Morro-Cabaña, and the Hotel Nacional. The hotel is a great place to light your first stogie, best enjoyed while sipping an añejo rum on the open-air patio bar. While here, enjoy your first taste of Havana nightlife at the Cabaret Parisien.
Aging Eisenhower-era vehicles wheeze along virtually any street in Havana. But for a close-up peek at the earliest exemplars, stroll through Habana Vieja and head for the Museo de Automoviles, one block east of Plaza de Armas. Displayed here are a 1905 Cadillac Model D… a 1926 Rolls-Royce Phantom… and revolutionary Comandante Camilo Cienfuegos’ 1959 Oldsmobile. Nearby, the Hostal Conde de Villanueva has an excellent cigar shop and VIP lounge.
In the afternoon, head to Fábrica de Tabaco H. Upmann for a guided factory tour, followed by a visit to the Casa de Habano, in Miramar; it’s considered the best cigar store in town.
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Renting a 1950s classic auto for the ride to Pinar del Río is tempting fate. Few are reliable! So arrange some other ride and journey out to Viñales—heartland of tobacco production. Dozens of private farmers grow tobacco, but be sure to visit Finca El Pinar San Luis, the farm of the Robaina family, a 90-minute journey further west at San Luis y Martínez.
Back to Havana today, calling at Il Divino to enjoy lunch before visiting the nearby Museo Ernest Hemingway, in Papa’s former home at San Francisco de Paula. Hemingway’s last vehicle, a 1955 Chrysler New Yorker convertible (currently under restoration), is to be displayed here. This evening hire your own classic 1950s convertible for dinner at La Guarida, followed by a show at the Tropicana cabaret.