Upon landing in Havana, time appears to stand still. All the postcard fantasies of vintage cars and colonial storefronts overwhelm with the accuracy of the reality—it could be 1950, 1980, or 2020—Havana is classically timeless. Though the realities portrayed are authentic, there is no denying the underlying turbulence of its past political climate, and the current tug-of-war between U.S.-Cuba relations. With this said, Cuba is indeed open to American visitors—and very much so welcoming of them—under the support for the Cuban people requirement. What exactly does this mean? For the Cuba-phile, you’ll have to forego the island’s tantalizing beaches, booking with companies like Cultural Cuba to curate an authentic, engaging itinerary, where you’ll discover exclusive access to enterprising locals, boutique accommodations, and incomparable experiences. It’s the ultimate opportunity to ensure immersive travel for tourists who want to absorb Cuban culture, while simultaneously supporting small businesses. Only a three-hour direct flight from JFK, here’s how to spend a weekend in Havana.
Where to Stay:
One of the many perks of booking with Cultural Cuba is access to a room at The Gran Hotel Manzana Kempinski La Habana; an ultra luxurious hotel occupying a former shopping arcade on the cusp of central Havana, bordering old Havana. The elaborate entrance is enhanced by oversized chandeliers and sets the tone to the majestic interiors found throughout its 246 guestrooms, two chic restaurants, two autonomous bars, and, yes, a snazzy cigar lounge. With so many worthy nooks to enjoy, Gran Hotel Manzana throws just one more at you with its rooftop pool overlooking the bustle of central Havana and esteemed El Capitolio. It’s a true gem at the heart of Havana, emphasizing all Cuban hospitality, has to offer.
(Editor’s note: American tourists are unable to book this hotel directly due to its placement on the Office of Foreign Assets Control Restricted List. In booking with Cultural Cuba, it is legal to stay here due to the company’s grandfathered access to its rooms).
Where to Drink:
With a history and culture steeped in rum and cigars, Havana’s social scene has long buzzed with salsa tempo and rum-forward cocktails. Though the majority of Cuban rum experts would advise sipping the sugarcane spirit neat, you’d be remiss not to savor a mojito in its birthplace. It’s believed that the first mojito was concocted at La Bodeguita del Medio, which is worth a visit if you’re interested in the drink’s history. Otherwise, variations of the mojito can be found throughout Havana, including the trendy La Esencia and Ernest Hemingway’s favorite watering hole, El Floridita, just across the street from Gran Hotel Manzana.
Where to Eat:
While Havana’s cocktail scene is well-versed, the city’s culinary scene is still developing. A number of young chefs have emerged from Havana within the past decade, and restaurants like 5 Sentidos have begun introducing contemporary flavors into traditional Cuban cuisine. Combinations like pork belly and passion fruit, arancini stuffed with ropa vieja, and lobster ceviche dazzle on the menu. For light bites in old Havana, Lamparilla 361 Tapas and Cervezas serves up an ever-changing menu to pair with local beers. Lastly, no trip to Havana is complete without dinner at Havana’s most famed restaurant, La Guarida. The sweeping staircase welcomes you to the old-world, colonial building for marlin tacos (you’re going to want to order more than one!) as well as its notable suckling pig, and ropa vieja, occasionally made with lamb rather than beef.
What to Do:
As a pleasant surprise, Havana offers a burgeoning arts scene. You don’t need to wander far to witness artists enlivening the streets with their striking paintings, yet, one of the prominent showrooms to view the wide array of talent is at the all-encompassing Fábrica de Arte Cubano—part art gallery, part discoteca. You’ll want to be sure to reserve an entire night here. Aside from paint on canvas, Cultural Cuba can introduce you to well-established photographers, budding fashion designers, and captivating musicians; upon booking, be sure to advise if you have any particular preferences so the company can arrange personalized interactions within the arts space.
You’ll find there’s no shortage of ways to spend your weekend in Havana, but be sure to reserve time to indulge in a cigar, which allows you to take a moment from the hectic whirlwind of touring and talking, to absorb Cuba through a different lens—a more relaxed and reflective angle to contrast the otherwise hustle of Havana.