Ever wanted to jump in a time machine and head back to the 1950s? Thanks to the Freedom to Travel to Cuba Act, you can.
Cuba is open for visitors, y’all – and while your Visa may suggest you’re heading south for “educational activities” or “humanitarian projects,” we recommend punctuating your adventure with good food, city tours, museum visits, and rum. Lots and lots of rum.
While it may look like a small island on the map, Cuba is dense with opportunities for adventure. If you can pop Out Of Office (see what we did there?) for 10 to 14 days, plan a road trip along Cuba’s rugged coast. However, if you’re hoarding your vacation days for a summer trip to The Hamptons or an autumn escape, you can experience the unique essence of Cuba with a quick trip to Havana over a long weekend.
Below, peruse the sights, bites, and excitement you can squeeze into a 4-day Havana getaway.
Sure, you can stay at Hotel Saratoga, (where Beyoncé and Jay-Z spent several days in 2013) or Hotel Parque Central (where a rooftop pool overlooks city and ocean) – but savvy travelers are invited to explore the ever-expanding collection of Air bnbs in Havana and beyond. Many of these safe and regulated establishments feature a live-in housekeeper (who often serves as a bartender), breakfast, and affordable wifi — which is hard to come by in Cuba. Plan a trip with a large group and split the cost of a multi-bedroom, modest mansion.
Marked by a towering brick chimney, El Cocinero is a rooftop bar and restaurant that attracts trendy locals, expats, and out-of-town purveyors of local flavor. Reserve your table at dusk – because nothing pairs better with a table of tapas than a pink sunset.
Located in the heart of Havana in an 18th century colonial building, Ivan Chef Justo serves up Mediterranean-inspired dishes like eel salad, cheese risotto, and suckling pig. Decorated with vintage mirrors and movie posters from yesteryear, this eatery is as charming as the food is delicious.
When seeking a distinctive dining experience oozing with hospitality, head to Cocina de Lilliam – or, in English, Lilliam’s Kitchen. This garden-style restaurant is peppered with antiques, features live music, and feels like your favorite Spanish aunt’s backyard. Grab the spicy paella, which can easily be split between four hungry diners, and a pitcher of sangria for a special treat.
When a midday sweet tooth kicks in, pop over to the Museo del Chocolate in Old Havana. A decadent glass of cold chocolate paired with fresh churros fried street-side make the perfect midday treat.
The country may be known for it’s sweet and refreshing mojitos (which are $4 at most restaurants and bars), but when you need a break from rum, head to O’Reilly 304. This Mediterranean-style bar, which would fit well in Manhattan’s West Village, is shaking up the best gin & tonics on the equator. Served in cavernous glasses and garnished with fresh fruit, cocktails are best enjoyed on the bar’s rooftop overlooking Old Havana.
Where do art, music, cinema, and rum collide? La Fabrica del Arte Cubano, a new hotspot erected on the outskirts of Havana, is a sprawling, converted warehouse that features rotating photography and film exhibits as well as nightly performances patrons can enjoy with a frozen mojito in hand. Here, Cuba’s young, hip, and elite dance and mingle with tourists in-the-know ‘till 2AM.
What makes a Cuban cigar so special? Why is Cuban rum so tasty? At the Museum of Cigar and Rum Museum, you can find out. Daily tours lead visitors through the cigar and rum manufacturing process. At the end of each, enjoy hands-on opportunities to make your own cigar or sample favorite rum cocktails.
How did Cuba transform from a thriving, mid-century destination where mob bosses and star-studded celebrities alike came to play and relax into a communist enigma closed to Americans? The Museum of the Revolution, housed in the country’s former Presidential Palace, explores Cuba’s tumultuous past through a series of photographs, artifacts, and exhibits. Outside the mansion, visitors can see tanks, planes, and boats that shape the history of Cuba’s military regime.
Toward the end of his life, Ernest Hemmingway fell in love with the color, culture, and creativity of Cuba. He purchased an estate in San Francisco de Paula, a seaside town nestled on Cuba’s northern coast. Peek into the home of a literary genius; this well-preserved manor features Hemmingway’s collection of books, taxidermy, and finds from his global adventures. See his Finca Vigia — or lookout house — where views overlook towns and forests. Marvel at his swimming pool – where he was rumored to host nude pool parties with Hollywood royalty. Finally, get up-close-and-person with his prized fishing boat, the storied Pilar. When you leave Hemmingway House, pop by La Bodeguita del Medio — Hemmingway’s favorite local bar – and grab a complimentary blue daiquiri.
After a few jam-packed days of strolling the streets of Havana, a quick escape from the city may be in order. A 1-hour drive leads to Las Terrazas, a serene ecovillage located in the lush hills of Candelaria. Become one with nature by strolling around the ecoresort — then, grab a cup of coffee (spiked with rum, of course!) at the shop attached to the property’s coffee plantation. Finally, adrenaline junkies can get their fix on a series of zip lines that soar above houses, lakes, and grassy valleys. Finish the day by cooling down with a dive in one of resident lakes or ponds.
You see them all over the city – candy-colored, vintage convertibles with fedora-wearing drivers smoking cigars. What better way to experience Cuba’s iconic taxis than with a joy ride to the beach? Book a multi-hour tour down to a beach with Cuba Classic Car Tours. There, grab a surfside cocktail, suntan or a few minutes of needed solitude by the clear, blue waters of the Atlantic. Don’t forget your most vibrant floral romper, statement shades and Bare Republic mineral sunscreen for this sun-filled, 1950s style adventure!
By Macy Sirmans