A Long Weekend in Cuba (And Why You Really Need to Visit Now)

The El Capitolio at dusk in Havana, Cuba.Photo: Alamy

Sure, we all fantasize of the day when we’ll have a week (or a few!) to devote to the vacation of our dreams—but really, who has the time? With the height of summer upon us, it’s high time to book your next long weekend getaway. Because every moment counts when you’re traveling for three days—and because location is everything when you’re in a time crunch—why not set your sight on someplace special?

Cuba may not be the first destination that comes to mind when contemplating a quick break, but if you’re in New York, consider the facts: You can count on spending three hours (if you’re lucky) in bumper-to-bumper traffic en route to the Hamptons—or you can hop a nonstop flight that will have you in Havana in three hours, easy. And with our current President cracking down on both travel and commercial ties relating to Cuba, there’s truly no time like the present to visit. Below, the best places eat, dance, sleep, and see art upon arrival.

Photo: Courtesy of Rachel Waldman

Where to Stay

Part of the appeal of—or depending on who you ask, challenge of—visiting Havana is that it’s not yet filled with the kinds of boutique hotels you might find on say, another Caribbean island. While government-owned hotels are certainly a viable option, they are likely to be flooded with tourists—and you can be sure they’ll cost you a pretty peso. Instead, good ol’ B and Bs—or casa particulares as they’re called in Cuba—(like Flor y Manu, which is located in the heart of Centro Havana) are the way to go. If you’re ready to rough it a bit, you’re guaranteed to receive an authentic experience, great hospitality, and the best home-cooked breakfast. If you feel like splurging, check into Paseo 206, a restored eight-room colonial mansion tucked away on one of the most trafficked streets near Plaza de la Revolución. Alternatively, La Reserva, a converted mansion in Vedado, strikes the perfect balance between retro charm and modern luxuries.

Where to Eat

The vibe in Cuba is generally laid-back and chill. The rise of privately run restaurants (aka paladares) vary from off-the-beaten-path operations, like Santy Pescador, to the sleek-and-chic, like Atelier, that bring a dash of style with savory food. Le Chansonnier, a family-run fine restaurant hidden in a townhome on a side street in Vedado, is easy to drive by and miss—but that doesn’t mean you should miss out. And of course, no visit to Havana is complete without a little live music. Don’t be fooled by Casa Miglis’s Swedish roots. The oh-so-cool refuge offers up some of the best ceviche and is a reliable spot for everything from reggaeton to salsa to merengue. If you’re seeking heart-stopping 360-degree views of the city, climb up the spiral stairs of El Cocinero, which gives way to a rooftop of strung lights and sharable dishes. Day or night, it’s a flytrap for an interesting and influential cast of characters. Be aware, though: Ask for a coffee and you’ll be handed the potent island variety. Love it or hate it, you’ll certainly remember it.

What to Do

Take a drive along the Malecón, the curvy seaside stretch of road that wraps around the city, in an old and slow Chevy (all the better to take in the breathtaking seascape). Channel Ernest Hemingway with a walk along the Prado. Bookworms must visit El Floridita, where the late literary writer made frequent stops between writing to sip on the mojitos. Once you’re fully hydrated, hit the bustling streets of Old Havana and stop into sweet spots like Clandestina, an art studio meets atelier, where you can pick up silkscreen-printed T-shirts and totes. Last but not least, a trip to Fábrica de Arte is sure to be the highlight of your stay in Havana.

During open hours (Thursday through Sunday nights), the factory space is filled to the brim with locals and visitors alike. Here, culture and conversation comingle, and because there’s so much art to see, live music to hear, and local clothing and accessories to shop, it’s easy to lose track of time. After you complete your walk through, finish off the evening with a nightcap at the open-ceiling bar.

Rachel Waldman, Vogue

July 27, 2017

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