Havana Nights

Conquering Cuba’s queer-friendly capital.

Story and photo by Joanna O’Leary

When President Barack Obama lifted decades-old regulations that made it prohibitively difficult for Americans to travel to Cuba, there was much rejoicing among the jet set. For years, our European counterparts have been able to journey unhampered to Havana to enjoy its storied colonial neighborhoods, charming paladars, and souped-up classic cars. Finally, it’s once again our turn.

But before you buy your tickets, you need to know about some minor restrictions on travel to Cuba. While the “official” motivation for your trip needs to fall under one of 12 categories, let it be noted that one of these categories is simply “support for the Cuban people.” This intrepid reporter cited “journalistic activity” as her motivation, and was not once asked to show any documentation supporting this claim. Many other travelers have reported similar experiences. You will also need a visa, which can be easily purchased via an online agency. (Depending on which airline you fly, you can sometimes purchase a visa at your point of departure.)

LGBT travelers should also note that although Cuba (and especially Havana) boasts a vibrant LGBTQ community and is generally welcoming, the country is still somewhat behind other nations with regard to widespread acceptance. Public displays of affection, especially in rural areas, may draw unwanted attention. But safe, fun spaces do exist—and here are some of our favorites.

Class and history converge at the Hotel Nacional de Cuba, which has been the place to stay in Havana for the past 80 years. Those into stargazing should take the hotel’s free historical tour, in which a guide shares anecdotes about celebrity guests (including Frank Sinatra, Rita Hayworth, and Mickey Mantle) and points out the rooms they stayed in. Notably absent from this list are Kim Kardashian and Kanye West, who opted to stay at a more modern resort when they visited the island last year. Big mistake, Kimye.

Even if you don’t stay at the Hotel Nacional, you can take advantage of their back-terrace bar for an evening drink and a look at the hotel’s posh retro décor. As the sun sets, an army of waiters ferries mojitos back and forth to couples and mixed groups of Europeans lounging on comfy garden furniture. For the best view (and equally diligent service), take a short stroll farther down the lawn to sit at a table overlooking the ocean. Although the dress code is casual, you’ll feel more in the mood swathed in pastel linen and sporting a fedora or cartwheel hat.

Then continue your evening tour at some of the city’s trendiest watering holes, clubs, and cafés. Recently highlighted by the New York Times, mYXto is a small, sleek bar that distinguishes itself from Havana’s other gay-friendly venues with its diverse spirits list—most welcome for those craving a change from Cuba’s ubiquitous rum—as well as decent nibbles like seafood tapas.

One step into Havana’s Sia Kara Cafe and you’d swear you’re in the heart of hipster Montrose rather than a communist capital. The airy, open bar and restaurant, whose walls are lined with pieces from local artists and black-and-white historical photographs, is filled during the day with fashionistas and business types lunching on ceviche. At night, tourists mingle (in a good way) while sipping rum cocktails under the glowing chandelier or in a side nook that’s cordoned off with men’s neckties (because, why not?).

Despite what some online reviewers might have you believe, Cabaret Las Vegas is not technically the only gay club in Havana, but its enormous popularity testifies to the consistently high quality of the drag performances. The mostly young crowd starts to really pack the club around midnight, so arrive earlier to reserve a table if you want to avoid standing.

If you turn into a pumpkin at midnight, other just-as-fabulous fun can be found at Tropicana, which hosts nightly entertainment starting around 10 p.m. To call what transpires there just a “show” is an understatement—the dizzying extravaganza of light, sound, and over-the-top costumed singers and dancers verges on sensory overload, in a good way. I have never seen so many feathers outside a chicken coop. Reservations are highly recommended, especially on weekends and during the high tourist season.

Finally, while Havana nights are heavenly, the daylight hours hold opportunities for more low-key cultural pursuits. The capital is very walkable, and a stroll through the Old Havana quarter enables you to stumble upon charming architecture and mom-and-pop joints—which, by the way, serve far better food than the government-owned restaurants. Both the Museo Nacional de Artes Decorativas and the Museo Nacional de Bellas Artes are worth visiting, the latter especially for its collection of works by Cuban artists. Or if you’re feeling lazy, just keep it simple and grab a cold drink, a book, and head to Malecón (a five-mile boardwalk affectionately deemed “Cuba’s couch”) to people-watch.


Joanna O’Leary

Joanna O’Leary is a regular contributor to OutSmart Magazine and a freelance food and travel writer based in Houston. Her exploits are chronicled on
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