Vacation Destinations

Classic Cuba

The candy-colored Oldsmobiles and tail finned Buicks lining the streets of Havana capture the nostalgia of a bygone era. Now, as this rediscovered island begins to accelerate with progress, more American travelers than ever are seizing the monumental moment to explore the country. Your trip to Cuba presents opportunities for exclusive privileges, including a personal concierge to anticipate your needs and private car service. Step into your very own time capsule, a vintage Pontiac convertible, to venture into Cuba’s history and forge lasting connections with its people.

With a guide in the driver’s seat, cruise by sun-brightened colonial buildings and Gaudí-inspired facades with their breezy central courtyards, Art Nouveau embellishments and high-arched doorways. At Finca La Vigía, Ernest Hemingway’s home for over 20 years, you’ll see the typewriter used by the iconic mid-century author to produce famous works, including The Old Man and the Sea. Then roll past the Miramar district’s Beaux-Arts mansions and modernist churches, which popped up almost daily during the thriving 1950s, on your way to Bodeguita del Medio — one of Hemingway’s favorite haunts. Sip the seaside bar’s specialty mojito, a refreshing highball infused with white rum, mint and muddled island sugar cane.

With taste buds primed for more Cuban flavors, set out on foot into Old Havana’s pedestrian-only network of 500-year-old cobblestone streets. Charming paladares, family-owned restaurants, cover nearly every corner of this designated UNESCO World Heritage site. Inside their cozy kitchens, learn to fold flaky pasteles according to treasured family recipes, then share lunch and conversation with the owners to discern their passion for local cuisine. Rejoin your private driver for a sunny spin down the Malecón, a five-mile promenade that unfolds along the city seawall, arriving at Habana Compás for a private performance of music and dance. Company members clack castanets and stomp with wood slippers, then explain the fusion of Spanish choreography and Afro-Cuban rhythms during a fun-filled meet-and-greet.

Continue your cultural pursuits at the Muraleando Neighborhood Community Art project, spotting the murals and found-object sculptures that adorn the barrio streets. While you visit with contributing artists, neighbors emerge to share food and festivities in a block party-like convergence that this project helped to cultivate. At dusk, sink back into the car’s plush leather seats before arriving at the Tropicana Club, where Nat King Cole and Josephine Baker once headlined the lavish stage shows that embodied Cuba’s nightlife. Watch the evening cabaret come to life with booming conga drums and dancers clad in elaborate fruit-and-feather-adorned headdresses, serving as a vibrant finale to your travels back in time.