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By Matthew Link

The Caribbean’s gay offerings are often characterized as dead on arrival. Only two destinations — Curacao and the Cayman Islands — do any kind of large-scale gay tourism marketing (the latter in a bid to reverse their previously anti-gay image). Besides the one-off gay-owned guesthouse or villa (some very basic) in random places like Aruba, St. Martin, St. Kitts, Bonaire, and the Dominican Republic, there is no real concentration of gay properties, nightlife, or attractions in the Caribbean. Sure, Cuba has a burgeoning and increasingly more visible LGBT life, but it’s still mostly underground and difficult for Americans to experience with embargoes against U.S. tourists spending money there. Places like Jamaica are renowned for being down-right gay hostile.

However, there are some glimmers of gay life amid all this heterosexualism. I just got back from the U.S. territory of Puerto Rico, and found it to be perhaps the gayest spot in the region, despite the main city of San Juan having seen gay guesthouses and bars closing their doors over the last decade. San Juan has that rarity in the Caribbean –- an actual bona fide gay beach in the up-and-coming district of Condado (think newly-opened Gucci shops and outdoor cafes), east of the colonial old town. I didn’t see it as packed with Speedo-clad men as, say, South Beach, but as I met many LGBTs I discovered that gay life in San Juan is surprisingly out and tolerated. The hotel behind the city’s main gay beach is called the Atlantic Beach Hotel, and although the property has definitely seen better days, it has a friendly outdoor patio bar overlooking the waves, where men hold hands while drowning rum and Cokes unharrassed. You don’t have to stay right there –- you can easily get to this gay beach via taxi while staying elsewhere. I recommend Old San Juan for its frozen-in-time colonial ambience, complete with blue cobblestone streets and ornate churches. Here, check into the luxurious four-star Hotel El Convento, actually housed in a former convent with sections dating back to 1651! Across the street is the gorgeous San Juan Cathedral, the Western Hemisphere’s oldest. To bask in another era, check into the Art Deco vintage Normandie Hotel, situated between Old San Juan and the Condado, built to look like an oceanline with panoramic views of the Atlantic.

After San Juan, I grabbed a puddle-jumper to meet some friends in the nearby British Virgin Islands. Known for their tiny population and a low-key but ultra Lifestyles of the Rich and Famous patina (Virgin Atlantic maverick Richard Branson actually owns an entire isle here), the last thing on Earth I was expecting was anything remotely gay. So imagine my surprise when I came across one of the most lavish gay-owned properties this well-worn travel writer has ever laid eyes on. It’s just opened, and it’s called Aquamare. Three huge, gorgeous, impeccably-decorated villas front a private beach on the isle of Virgin Gorda. It’s the kind of place reeking with five-star treatment: a private chef serves up island-fresh gourmet meals in an enormous, state-of-the-art kitchen; maids clean up after your every move (even though this is technically a vacation rental and not a hotel); and a professional masseur visits your palatial room to work out any knots you may have brought with you. Infinity pools, on-site snorkeling, kayaking to empty beaches, Fette towels, Bulgari toiletries, cathedral ceilings, designer furniture -– you get the picture. If you get bored, there’s even a $1 million, three-story, rapper-worthy yacht you can ask to take a sunset cruise on. No wonder Harrison Ford, Calista Flockhart and Rihanna have all checked in here already, even though Aquamare is less than a year old. After having spent days watching the cracks form in the walls of the Atlantic in San Juan, I was left wondering: Why can’t more gay-owned properties be like this??

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Matthew Link is the Editor At Large for The Out Traveler magazine, as
well as a contributor to Newsweek. Having been to over 60 countries and
all 7 continents doesn’t keep him from getting on the next plane away
from his home in New York City.

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