Puerto Rico’s poorly defined relationship with the United States (is it the last remaining colony in the world? discuss!) has distracted from the island nation’s many virtues, virtues that are especially appealing for LGBTQ2S+ travellers. The culture, the landscape, the food, the history, the fun-loving locals (who call themselves Boricuas), the party scene—mwah!
Of the Caribbean islands, Puerto Rico, which has a population of about 3.2 million residents (and it hosts almost as many visitors each year), is easily the most welcoming to LGBTQ2S+ travellers. Gay nightlife and queer culture are openly celebrated, and same-sex couples can be seen walking around holding hands not just in the capital, San Juan, but also in less urban areas. When same-sex marriage was legalized in 2015 in the U.S., that Supreme Court decision applied to Puerto Rico, too.
Despite the United States’ furnishings—the U.S. dollar as currency, U.S. Postal Service mailboxes, the ease of getting around in English (though Spanish is dominant), Americans not needing a passport to visit—Puerto Rico is most definitely a Latin American destination. Gorgeous Spanish colonial architecture dating back to the early 1500s defines the capital—no wonder Old San Juan is a must-visit port in many Caribbean cruises—and other historic towns and cities. It’s not just the buildings that exemplify Latino culture; there are moments on weekends when whole neighbourhoods feel like they might break out dancing to salsa or the latest Bad Bunny hit. There’s something musical in the water. One of the country’s main cultural exports, in the days before Bad Bunny took the top spot, was Latin pop sensation Ricky Martin, who became famous at age 12, coming out in 2010 at age 39.
Unlike some sun-drenched destinations, where the corralling of tourists and onerous disparities in income can create barriers between visitors and locals, Boricua culture, politics and economics make it easier to meet and interact with locals on equal footing; visitors enjoying Ocean Park Beach—one of the San Juan’s nicest, home to many of its cooler hotels—might notice that many of the other people enjoying the water and sand live in the same upscale neighbourhood. Not far away, in the Condado neighbourhood, a mix of small and large hotels provide easy access to a gay-friendly beach area and are within walking distance (or a short Uber ride) from some of Puerto Rico’s biggest gay nightclubs. If all-inclusive is more your style, the beaches of Isla Verde, farther to the east, might be your stomping grounds.
Although its beaches are beautiful, the nightlife on point and the hospitality industry well developed, Puerto Rico’s little secret is that there’s much more to do than just sipping piña coladas poolside. Rent a vehicle and head up into the Cordillera Central, the mountains that divide the north from the south, where, at certain peaks, you can see both sides of the island. In the southwest, the rolling mountains are perfect for growing coffee and chocolate, though what is produced there is now more artisanal, less industrial than it once was. Hop a small plane or a ferry and land on the verdant island of Vieques, which, after the the departure of the U.S. military 20 years ago, is providing a fresh canvas for entrepreneurs, many of them LGBTQ+, to found restaurants, guesthouses, gift shops and outdoor-adventure companies that are truly in tune with what contemporary visitors want to do and see.
Puerto Rico’s history—as a colony of Spain where Indigenous people were ruthlessly killed, as a cog in the African slave economy, as a territory that the U.S. has used and abused for its own purposes—is tangled. The nation is still a work in progress. That’s part of what makes the place not only fun but fascinating. That piña colada you’re drinking, that pretty door you’re photographing, the rainbow arch you’re walking through to get from the cruise ship terminal to the historic centre—they all tell a story. And it’s a much more compelling story than you’d imagine from a quick stop during a Caribbean cruise or a week’s package holiday at a resort (though those two types of holidays have their pleasures). Puerto Rico, as a destination, makes you want to get out there and put yourself in the mix.
What to see and do
San Juan Pride (May 31 to June 1, 2024). Puerto Rico’s largest Pride is usually held in early June, with a range of parties and shows, and a Saturday parade starting at Parque del Indio (off Ave. Ashford in Condado). But San Juan is not the nation’s only Pride. Several of Puerto Rico’s 78 municipalities host LGBTQ2S+ celebrations, including Vieques (Adventura is a four-day festival in October), Boquerón (Orgullo Boquerón takes place in June) and Cataño (Cataño PRIDE Festival takes place in June). Puerto Rico Queer Filmfest usually takes place in November.
El Castillo San Felipe del Morro and Castillo San Cristóbal (each located on the opposite end of Calle Norzagaray, Historic Centre, Old San Juan, San Juan). These two fortresses, which form the core of the San Juan National Historic Site, were one of Spain’s first lines of defence against naval attacks against its interests in the Caribbean and Latin America. San Cristóbal in particular is considered the largest fortress built in the Americas and took more than 150 years to complete. Even if you’re not a history buff, the views from the tops of the walls are worth checking out.
Old San Juan/Viejo San Juan. Founded in 1521, the Puerto Rican capital was originally intended as a no-frills garrison town for the military. But over time, the Spanish invested in it as a piece of Europe in the Americas, including shipping over cobalt blue tiles for the cobblestone streets. When the historic architecture was falling into disrepair in the early 20th century, politician and activist Luis Muñoz Marín came up with a program to rejuvenate the downtown, which included rules about painting each building alternating pastel colours, a policy adopted by many Latin American cities that we now consider cute. With its plazas, waterfront vistas and narrow streets, it’s now a very photogenic area to explore. The daytime businesses tend to cater to the desires of cruise ship passengers—cheap T-shirts and souvenirs, some locally made, some made in China. At night, Old San Juan attracts an eclectic range of partiers with its many bohemian bars, some fancy, some countercultural. (More on that below in “Where to party.”)
Pulse Memorial (Polvorín San Gerónimo de Boquerón, San Juan). This monument, composed of seven pillars, each a different colour of the rainbow, was designed for a happy occasion: to commemorate the 2015 U.S. Supreme Court decision legalizing same-sex marriage. But when the Pulse nightclub shooting happened in Orlando, Florida, on June 12, 2016—a horrific event that killed 49, almost half of Puerto Rican descent—the monument was rededicated to honour the victims. It’s near an LGBTQ+-themed mural between a sports field and a stadium.
Rainbow City Gate (Cll. Marina and the exit to Pier 1, Old San Juan, San Juan). This rainbow gate, which many cruise ship passengers pass through as they leave their ship to explore Old San Juan, has a wild history. It was approved by former Puerto Rican governor Ricardo Rosselló, who had outwardly supported same-sex marriage, same-sex adoption and a ban on conversion therapy. But in 2019, leaked chat messages from Rosselló revealed the governor had insulting views—he mocked women, LGBTQ+ people and everyday Puerto Ricans. Large protests drove Rosselló out of office in 2019, and it’s said that his wife, Beatriz Areizaga, angrily ordered the gate painted white during his final days in office. Local activists repainted it the rainbow colours, but they lost some of the inspirational words that were part of the original.
Condado Beach (along Avenue Ashford between Puente Dos Hermanos and Calle Cervantes, San Juan) and Ocean Park Beach (along Boulevard Park between Avenue Washington and Calle Almendro, San Juan). These two strips of white sand along the Atlantic coast are among the nicest and more accessible city beaches in San Juan. The small, medium and large hotels in these areas are mixed among pleasant residential neighbourhoods, so there are eats and shopping with the budgets and tastes of Boricuas, not tourists, in mind. Both beaches are said to be cruisy after dark.
Santurce. Though Santurce is the name of the large district that compromises the whole peninsula that runs from Old San Juan to the resort-y area of Isla Verde, when a hipster tells you to hang out in Santurce, they are referring to the working-class-but-artsy area south of Condado. Santurce is home to the Museo de Arte de Puerto Rico (299 Ave. José de Diego, San Juan), the Museo de Arte Contemporáneo de Puerto Rico (1220 Ave. Ponce de León Esq. R.H. Todd Pda 18, San Juan) and the Centro de Bellas Arts Luis A. Ferré (Ave. Ponce de León Pda. 22 ½, San Juan), which showcases theatrical and musical performances. Several gay clubs (please see “Where to party” listings below) are in Santurce, but the area is better known as the home of Plaza del Mercado, usually called La Placita (1348 C. Jose M. Raffucci, San Juan), an open-air party where locals and visitors from all walks of life gather, volume way up, on weekend nights.
El Yunque National Forest. Mainland Americans love to claim this chunk of natural splendour, the only tropical rainforest in the U.S. forest system. About a 40-minute drive out of San Juan, this mountainous park (the peak is just over 1,000 metres) has waterfalls and a wide range of birds and animals that will make nature lovers swoon. There are several trails that can be hiked independently or as part of a group tour.
Vieques. About 32 kilometres long and only seven wide, this verdant tropical paradise used to be a U.S. military playground—they tested weapons here until 2003. In the 20 years since, creative entrepreneurs have been turning the island into a playground for visitors. Activities on the island’s menu include rum tasting at Crab Island Distilleries (off Route 200, west of the airport), horseback riding (I went with the Esperanza Riding Company), hiking and snorkelling (Sarah Elise at Crystal Clear Vieques does an excellent job of getting your mask fitting right and making you feel comfortable underwater). Vieques is also home to one of the world’s handful of bioluminescent bays, Puerto Mosquito. That is, water that lights up when something—an oar, your hand, a fish—brushes up against microscopic creatures known as dinoflagellates. Local tour operators, like the very friendly Black Beard Sports (53 Calle Benitez Guzman, Vieques), take you out at night in kayaks or other non-motorized vessels and show you how to make it glow. It’s hard to get a great photo, but it’s a magical once-in-a-lifetime IRL experience. Check out “Where to Stay” for accommodations in Vieques.
Where to stay
The Tryst Beachfront Hotel (1 Cll. Vendig, San Juan). If your PR goals are beaches and gay bars, then you can’t go wrong with this spunky, gay-friendly indie hotel, located right on the gayest part of Condado beach and only a five-minute drive or a 15-minute walk from San Juan’s biggest gay venues. The rooms are comfortably low-key, but the property began a major renovation in the fall of 2023 that should pump up the glam. Guests get access to a Rocky Balboa-style gym next door. They host drag brunches.
Condado Ocean Club (1045 Ashford Ave., San Juan). Whether your room is in the front or back of this adults-only property, you’ve got a view: the Atlantic or Laguna del Condado. Their acclaimed DECK, which has an infinity pool that juts out toward a semi-private beach, is an ideal place to mix and mingle with fellow guests.
Trópica Beach Hotel (1853 McLeary Ave., San Juan). It’s not exactly on the beach, but the friendly staff at this stylish and compact hotel will provide you with a folding beach chair, as well as a towel, that you can take with you on the two-minute walk to the nearest stretch of sand in Ocean Park. You won’t be doing laps in the small swimming pool, but it’s a fun place to fraternize.
Don Rafa Boutique Hotel & Residences (601 Ave. Miramar, San Juan). If you’re in Puerto Rico for work, you may want to be in close proximity to DISTRITO T-Mobile/Puerto Rico Convention Center, where so many deals go down. The Sheraton Puerto Rico Resort & Casino (200 Convention Blvd., San Juan), right in the middle of the action, is a full-service resort-style hotel that will help you balance work and pleasure. But if you’re looking for a more unique boutique experience just outside the convention district, Don Rafa has sumptuous 1950s-style decor that will transport you back in time when you’re not networking. Even if you’re not staying here, have a drink in the bar; wear a bow tie or an evening gown (or both) for full effect.
Fairmont El San Juan Hotel (6063 Ave. Isla Verde, Carolina). With four pools, eight restaurants (plus a Starbucks), five bars, one nightclub, extensive spa services and a casino, you might get through a whole week at this top-notch property without realizing that a sweeping two-kilometre beach is right there, just past the poolside cabanas. Sammy Davis Jr., Nat King Cole, Frank Sinatra, Eddie Fisher, Carol Channing and Liza Minnelli all performed here during the property’s first few decades, after it opened in 1958. These days, as an Accor property, inclusiveness and diversity are taken very seriously.
Hotel El Convento (100 Cll. del Cristo, San Juan). Built, of course, as a convent in 1646, this architectural gem was first transformed into a hotel in 1959. With 81 rooms, a pool and a fitness centre, it’s one of the most stylish hotels in Old San Juan.
Casa de Amistad (27 Cll. Benitez Castano, Vieques). First opened by a gay couple more than 20 years ago, and run for the last five years by another gay couple, John and Mike, this eight-room guesthouse has attracted a devoted ever-returning clientele, both straight and LGBTQ2S+—and it’s easy to see why. The rooms are well appointed, stylish and spacious, especially for the price point. Bonus points for the attention to detail: for example, access to a full-service kitchen for making picnic lunches to take to the beach, as well as coolers for transporting said lunch. Enjoy a beer or a cocktail with fellow travellers by the cute pool.
Where to eat
Semilla Kitchen & Bar (57 Cll. Delcasse, San Juan). This LGBTQ2S+-friendly favourite in Condado has brilliantly executed local and international dishes; they have the best risotto I’ve had in forever. Elevated casual dining with imaginative signature cocktails.
Raices Urbano (1961 Cll. Loíza, San Juan). The cocktail and beer menus are the stars at this local hangout, but you won’t be disappointed with the food, which ranges from tacos and shrimp cocktails to various steaks.
La Taberna Lúpulo (151 Cll. de San Sebastián, Old San Juan, San Juan). The tattooed staff at this countercultural pub serve tacos, sandwiches and an array of beers from their extensive draft list. They’re also known for their beer cocktails—bourbon, bitters and Scotch ale, anyone? We could have easily listed this under “Where to party” except it’s a great place to stop for lunch while wandering around Old San Juan.
Deaverdura (200 Cll. Sol, Old San Juan, San Juan). The atmosphere is no-frills at this LGBTQ2S+-friendly eatery, but the food—classic Latin American dishes like ceviche and hearty beef stews—is prepared with much love and care.
Juanes (201b Cll. Tetuán, Old San Juan, San Juan). Located in the middle of Old San Juan’s tourist zone, this easygoing oasis is a great place to try mofongo, one of Puerto Rico’s signature dishes. It’s usually made of mashed plantains, garlic and pork skin, and often topped with a red shrimp sauce, but there are so many variations—a visitor could make a project out of tasting mofongos all over the island.
El Punto Vegano (esq El Tren, 6 Cll. Wilson, Cataño). A ferry ride across the Bahia de San Juan from the capital, the suburban municipality of Cataño is a place with lots of waterfront bars, which makes it popular for weekend excursions. The municipality hosts an annual Pride celebration and has a rainbow-themed pier on its boardwalk. It’s also home to this cozy vegan restaurant, which serves filling and creative vegan dishes like meatless relleno de carne molida.
El Plaza Vieques (Cll. Carlos Lebrum, Vieques). Located in the historic town square of the main community of the island of Vieques (called both Vieques and Isabel Segunda), this upscale cantina has a wide-ranging menu designed for all appetites, and an excellent array of cocktails. Try the halibut with risotto with a gin-based Aperol twist.
Carambola (inside Blue Horizon Boutique Resort, Carretara 996 Km 4.3, Vieques). One of Vieques’ best-known properties—a favourite spot for weddings and special occasions—has an excellent restaurant that serves hearty breakfasts, tasty lunches and tropically inflected dinners.
Where to party
San Juan’s capital-G gay clubs and bars are clustered around Avenida Roberto H. Todd in Santurce, just south of the gayest part of Condado. They’re not far from the straighter nightlife hub of La Plazita, so it’s easy to bounce back and forth between the super gay and the less gay. But there are queer-friendly venues all over the city and the island.
Kweens Klub (1211 Ave. Manuel Fernández Juncos, San Juan). Opened in December 2021, this dance-drag club probably has the nation’s biggest queer dance floor, as well as an outdoor lounge. They host special events, as well as drag shows and karaoke.
Toxic Night Club (613 Cll. Condado, San Juan). A little drag, a little dancing to circuit music, a little stand-up comedy, some strippers—this hetero-friendly nightclub has something for everybody.
SX The Club (1204 Ave. de la Constitución, San Juan). This cruisy male-oriented club, which bills itself as “hardcore,” is dark and cavernous, with lots of nooks and crannies in which to get to know fellow patrons. Electronic dance music and drink specials.
Oasis (6 Ave. Condado, San Juan). Just off Condado beach, this indoor-outdoor LGBTQ2S+ lounge is the perfect place for taking a break from sunbathing or grabbing an early evening drink before hitting the clubs. Located to the side of the Sandy Beach Hotel.
La Sombrilla Rosa (154 Cll. de San Sebastián, Old San Juan, San Juan). When the cruise ships have left for the day and it gets dark in Old San Juan, the cool kids come out to play in the historic centre. This beloved queer bar, with its campy pink decor, is a welcoming place to meet other queers, both local and international, and the straights who wander in because the room is so enticing, the music so good and the drinks so cheap.
La Factoría (148 Cll. de San Sebastián, Old San Juan, San Juan). This stylish LGBTQ2S+-friendly bar, which has several retro-vibe rooms, is known for its cutting-edge cocktails.
El Local en Santurce (1425 Ave. Manuel Fernández Juncos, San Juan). This LGBTQ2S+-friendly dive bar in Santurce has live music—come here to see Puerto Rico’s next breakout act. Karaoke on Tuesdays.
Xteamworks Bath House (1752 Ave. Manuel Fernández Juncos, San Juan). Puerto Rico’s only gay bathhouse is open 6 p.m. to 11 p.m. Friday to Sunday. Think gloryhole, dark room and sling. Membership, which you can buy on arrival, is required.
Where to gear up
Anthony Quintana Store (1805 Ave. de la Constitución, San Juan). Designer, entrepreneur and TV personality Anthony Quintana is known for his playful clothing designs for all genders, but particularly his creative (and skimpy) men’s underwear.
Monsieur (1126 Ave. Ashford, San Juan). Have a fashion emergency that requires a shirt with bright geometric patterns or a well-tailored jacket? This multi-brand men’s shop has the cure.
El POP Santurce (1116 Ave. Ponce de León, San Juan). This multipurpose space promotes the works and projects of local artists and entrepreneurs, many of them LGBTQ+. You’ll always find books, but depending on when you visit, you might find posters, contemporary fashion, vintage clothing or yoga classes.
Librería Laberinto Viejo San Juan (251 C. de la Cruz, Old San Juan, San Juan). This well-organized and friendly mainstream independent bookstore has some LGBTQ2S+ titles.
Plaza Las Américas (525 Ave. F.D. Roosevelt, San Juan). The biggest mall in the Caribbean has most of the mainstream international brands you’d expect to find, though it leans more U.S. (Hollister) than Euro (no H&M?).
