Hemingway, Sugar, and Cigars: A Travel Guide to Cuba

With loosened restrictions, the gates have opened for curious travelers

Cuban flag

Cuba is every bit as romantic and stuck in a bygone era as we imagine it. In one of those sneaky (but completely legal) ways, I was able to visit Cuba just over a decade ago and I found cars from the '50s in front

of crumbly apartment complexes and ice cream stands and fruit juice carts pressed against each other on tiny one way streets. For me, the most thrilling discoveries were that people really dance in the streets to sultry Cuban music and that the best food really is served in paladares, family-owned restaurants often in private homes. (Photo courtesy of Flickr/Iker Merodio)

Now that President Obama is slowly easing travel restrictions for Americans, Cuba is easing its way back into place as an appealing destination for the jet-set. And for good reason. Tours and travel agents who specialize in travel to Cuba (read: making sure Americans go the legal way) are planning ever more trips and companies like Abercrombie and Kent are jumping on the bandwagon with bespoke trips of their own.

Called “The Forbidden Isle Revealed,” A&K’s first Cuba trip stops first in Trinidad, a UNESCO World Heritage Site, to walk down old cobbled streets and into the Romantic Museum, duck into the Manaca Ignaza Estate for cocktails and a chat about Cuba’s sugar industry, and learn to salsa dance. Moving on, the tour stops in Old Havana with a local guide who’ll take guests to a cigar factory and to the Rum Museum. Then, before a tour of the Museum of the Revolution, guests will take in the sights, sounds, and tastes of Hemingway’s Havana.

Hemingway knew Havana in and out — his modest room at the Hotel Ambos Mundos, where he is said to have written For Whom the Bell Tolls, had the perfect view of Havana’s bustle below and La Floridita still honors his memory by preserving his preferred bar stool and serving his favorites like

their daiquiris and a baked Alaska. The less fancy La Bodeguita del Medio is where he found his favorite mojito and dined on classic Cuban food. When he needed a break from city life, he retreated to his home in the small, idyllic fishing village of Cojimar, where he dined at Las Terrazas and, appropriately, wrote The Old Man and the Sea. (Photo courtesy of Flickr/World View)

A&K’s tour then moves on to discover other regions of Cuba like the Pinar del Rio province up in the mountains where travelers will visit a working farm as well as an indigenous limestone Indian cave and the Santeria-influenced area of Guanabacoa, just outside of Havana. 

Since Americans can only travel to Cuba with a certified group, accommodations will likely be taken care of. But if you’re group isn’t staying at the Hotel Nacional de Cuba, you should insist on at least a cocktail or dinner in the historic hotel. It is overwhelmingly beautiful with a pronounced old world feel. In keeping with that theme, a visit to the Nacional Ballet de Cuba is a must for manifold reasons. The grand, if crumbling, headquarters are filled with a history so rich it emanates from the walls and the dancing within is mesmerizing. The neighborhood that surrounds it is, also, worth taking a stroll in for its museums and cafes that abound.