For the greater part of the last century, Cuba has been a country shrouded in mystery, intrigue, and nostalgia, making it a destination of choice for intrepid travelers. For Americans, a trip to Havana came with its own unique set of bragging rights, because getting there took a great deal of effort—and, well, wasn’t always technically legal.
The recent normalization of relations with the United States means that access to the Caribbean island is changing rapidly. With the outcome of foreign investments and mass tourism unknown, there’s a palpable sense of urgency to experience the country’s muted glamour and time-capsule allure while it lasts. To abandon modern technology and creature comforts. To follow in the boozy footsteps of Ernest Hemingway. To learn to dance the rumba. To explore the politically driven art scene. To hail a classic 1950s DeSoto.Cuba, a country on the verge of change, is calling. These are the places to go find it.
Approaching its 10th year in business, La Guarida is still the paladar in Cuba. Despite its well-known reputation (Beyoncé and Jay-Z dropped by on their notorious anniversary tour), the restaurant feels like a delightful local secret.
The dramatic entrance entails walking through a spectacularly dilapidated building formerly known as La Mansión Camagüey and two flights up a winding marble staircase. Parts of the worn mansion are residences, so you’ll encounter signs of everyday life—a flickering television set, drying laundry—as you enter the family-run restaurant, where a handful of small dining rooms are drenched in candlelight and filled with fine linens, fake flowers, and religious icons. It’s one part kitschy, two parts cozy, and totally different than anywhere you’ve ever eaten.The food is good, if a tad rustic. Thanks to the country’s limited access to quality ingredients, this likely won’t be the best meal you’ve ever tasted, but you’ll remember the experience. Order the tiny taco trio, watermelon gazpacho, and one of their fresh seafood dishes. Reservations are a must.
Fábrica de Arte Cubano
When Cuban musician X Alfonso converted the original headquarters for Havana’s electricity company into an avant-garde art space, he had no idea how successful the venture would be. Now a place for well-off Cubans and tourists in the know, Fábrica de Arte is one of the most exciting things happening in Havana’s contemporary cultural scene.
The maze-like industrial factory houses a music venue, cinema, exhibition hall, art gallery, fashion boutique, bars, and cantina—an impressive assortment that can lead to a trippy evening more befitting of a night out in Berlin or Brooklyn. One minute you’re taking in contemporary art, the next you’re dancing to techno with new Cuban friends, mojito in hand.When you arrive and pay your entrance fee, you’re given a card resembling the Cuban ration booklet. This is where your food and drinks are marked so you can pay all at once on your way out. Don’t lose it, or else you’ll be charged $30 CUC—about one-third of an islander’s weekly salary.
For a closer look at experimental Cuban art, head to Factoría Habana, a multi-level gallery in Old Havana run by the City Historian’s Office with a mission to connect Latin American and European art. The crumbling, 20th-century colonial building has been modernized with polished concrete floors, white walls, and high ceilings by architect Abiel San Miguel. A large skylight was added to increase natural sunlight. Exhibitions feature established and up-and-coming local artists like René Francisco, Rocío García, and Carlos Montes de Oca.
Dance is revered in Cuba. The Cuban National Ballet is not only a source of local pride, but also one of the world’s best ballet companies. What sets them apart on the international stage is the artful blend of classical training with what can only be recognized as a uniquely Cuban sensuality. Founded by prima ballerina Alicia Alonso, the state-funded company has been supported by Castro since he ousted Batista. Performances have been traditionally held in the Gran Teatro de La Habana, an impressively ornate and historic building currently undergoing renovations. In the meantime, shows like Don Quixote, Giselle, and other classics are held at the nearby Teatro Nacional de Cuba. Tickets are one of the best deals you’ll find in all of Havana.
Hotel Habana Riviera
If the city’s classic Cadillacs make you weak in the knees, plan an afternoon of vintage Cubana at Hotel Habana Riviera. The Mad Men–era hideaway was built by legendary mobster Meyer Lansky in the 1950s, and was inspired by Las Vegas’ legendary Riviera Casino. In its heyday, the Habana Riviera hosted a who’s who of mid-century Hollywood: William Holden, Jean Fenn, Nat King Cole, and Ava Gardner.
In Havana, basic amenities like hot water, Wi-Fi, and electricity can be non-existent—even at the island’s nicest hotels—so the best hotel option is a small bed-and-breakfast. The finest, like Suite Havana, offer a more modern and comfortable experience. A calm and stylish two-bedroom retreat atop a colonial building on a discreet side street in Old Havana, it’s close to the neighborhood’s many charming squares and modern cafes, like Doña Eutimia and Bar O'Reilly 304. Owners Lea and François have personalized the apartment with handmade furniture alongside their collection of contemporary Cuban artwork. They come by every morning to serve a traditional Cuban breakfast of tropical fruits, eggs, pastries, and shakes made from mamey, a sweet salmon-colored fruit native to the region.
The apartment is spacious and sparkling clean, with double beds, floor-to-ceiling windows, and air conditioning units—a much-appreciated amenity when the sweltering Caribbean sun sends you inside for a siesta. Wrought-iron balconies overlook lively Café Lamparilla, where musicians serenade daiquiri-sipping patrons and passersby with a rendition of “Guantanamera.”
Head to the sweeping private roof garden to smoke a Cohiba (extras are kept in a cigar box near the sofa) amid overgrown palms, ferns, and orchids. Or take advantage of the 24-hour concierge service for recommendations and help with booking excursions.
Cuba is a joyful country, but hardships are real. The everyday supplies Americans take for granted can be difficult to find in Havana. If you want to devote some of your trip to giving back, an easy way to do so would be to pack over-the-counter medications, paper goods, toiletries, and small toys to drop off at the local Cáritas Cubana (calle d, no. 512, bt 23rd and 21st) or Children's Ministry (Maceo 24909, at Caña y Pañuelo Diezmero; San Miguel del Padron).
- © Leo Mason Travel photos / Alamy Stock Photo
- PHOTOGRAPH BY ARTMARIE
- PHOTOGRAPH BY JON ARNOLD
- PHOTOGRAPH COURTESY OF FÁBRICA DE ARTE CUBANO
- PHOTOGRAPH COURTESY OF FACTORÍA HABANA
- PHOTOGRAPH COURTESY OF BALLET NACIONAL DE CUBA
- PHOTOGRAPH BY LEO MASON
- PHOTOGRAPH COURTESY OF SUITE HAVANA