Johnny Depp’s verdict on his own debauched and gonzo trip to Havana with Hunter S. Thompson could ably describe our collective understanding of Cuba and her history as a whole: “It was totally ludicrous and surreal.”

Because what do we see of Cuba, really? Looking through a lens made opaque by a censorship that generally conforms to the ideological and economic embargo of the last fifty years, and perhaps by our own assumed political superiority, our picture is impressionistic at best.

No surprise, then, that what we think we know of the island nation ninety miles off the Florida Keys is in fact histrionic inflation of the good and the bad that has existed there. We have in our mind Hemingway’s butch haven for swarthy adventure. We have Che’s martyred commitment to rebellion. We have the Bay of Pigs and the secret campaigns of the CIA to “whack out the Beard,” as Joe Pesci’s Agency contractor in JFK says of the numerous and increasingly buffoonish attempts to assassinate Castro. We have the nearly slapstick idiocy of intelligence agencies and generals, ours and theirs, who, operating out of fear and paranoia, nearly blew up the world in October 1962.

When we look at our idea of Cuba past and present, we see extraordinary disparity, economic and otherwise: Hyman Roth and Michael Corleone gambling at the Riviera Hotel in The Godfather: Part II; Slim Aarons’s images of an entitled jet set hopping around an aquamarine pool while plantation workers were exploited to medieval extremes in the Batista era. We are given the picture of a land of wild, Jungle Book fecundity in flames. This latter impression is reinforced, fittingly, in part by the 1964 Soviet-funded, Fellini-esque masterpiece that is I Am Cuba, a film despised at the time of its making in both Cuba and the USSR, but now rightly beloved as one of the best movies ever made anywhere. The Castro era, (Fidel’s first, and now Raúl’s) which announced itself with the film’s corrective vision of the island’s purity, is generally characterized, in very broad strokes, as draconian repression in service of beautiful ideals—world-class health care, but allowing only a chosen few to access it; baseball gods on hellish diamonds; a tumble-down postcolonial mansion. But these sensationalized extremes of splendor and decay are just that, and taste of the myths we’ve been spoon-fed.

The real Cuba, then, as the guidebooks would call it, is hidden—up a winding staircase, maybe, through the back room of someone’s home, where you’ll discover the splendor of paladares, the great gray-market dining operations run by regular families. The real Havana remains a trapped-in-embargo-amber version of the city as it was in 1959, when Che and Fidel marched in from Santa Clara. But the amber, hopefully, begins to crack.

On December 17, 2014, President Obama and Raúl Castro announced their decision to ease ties between the two countries, reopening embassies in one another’s capitals, easing restrictions on trade and travel, and, significantly, removing Cuba from the list of countries harboring terrorists. The long-term effects of this process are of course impossible to project, but any lessening of enmity and secrecy are reasons to rejoice immediately. A new flood of congress cannot help but to illuminate some of the shadier areas of our understanding, even if it comes at the point of a Starbucks franchise and trailing a tyranny of Instagram posts and travel shows selling us on the island’s hippest enclaves. The time to go is now.

There are three options available to Americans who want to visit the island: fly in anonymously from a country not the United States, and carry only cash; have a close family member who resides in Cuba, and requent permission; or sign up for one of the people-to-people exchanges—sort of mini cultural ambassadorships—currently selling out months in advance.

Looking at the pictures in this portfolio, long lines and a little bureaucracy will seem a small price to pay to get to Cuba right away. In the words of the late Dr. Thompson, looking forward to his balcony suite at the Hotel Nacional, you might say, “I am going to Cuba to pay my respects to the Cuban people ... But I am mainly going for Fun.”

Contact us to book your trip to HavanaInquire now

View Feature
Three floors up in a crumbling century-old mansion, this atmospheric privately-owned restaurant is routinely cited as Havana’s finest. Go for Cuban specialties.
City Spotlights
View Feature
City Spotlights This 427-room hotel has a solid rooftop pool and the most buzzing lobby in town. The location, on the edge of Old and Central Havana, puts you within easy walking distance of the shops and bars on Calle Obispo and Paseo del Prado.
View Feature
Nightlife In operation since the 1930's, this legendary cabaret was once famous for its sumptuous performances and beautiful showgirls. The scene isn’t as over-the-top today, but the show—complete with sequined g-strings and feather headdresses—goes on, in open air if the weather permits.
View Feature
Special Habanos, Cohiba, Monte Cristo, Romeo y Julieta, and (of course) Partagás are among the brands still being produced at this 170-year-old factory, with its handsomely faded neoclassical façade. There’s also a museum, shop, and cigar-making school.