San Juan Travel Guide

Three things that rarely go hand-in-hand for gay travellers are top-tier cities with top-shelf beaches that are legit gay-friendly. Well, this rainbow unicorn exists and it’s called San Juan. The capital of Puerto Rico is one of the few cities in the world, and the only one in the Caribbean, that checks all those boxes and then some: the colourful colonial architecture, the cobblestone streets, the picture-perfect beaches, the 16th-century landmarks, the James Beard-awarded restaurants and bars, and the banging gay scene. San Juan is the undisputed queen of LGBTQ+ nightlife in the Caribbean. This place sparks joy, people. The kind that makes you want to yell, “Woo-hoo!” or, as the Puerto Ricans would put it, “¡Wepa!”

Serafina Beach Hotel, the first new resort to open after Hurricane Maria, is a sleek, swanky testament to the resiliency of the island

The best hotels in San Juan

You have to imagine that a hotel built in a monastery adjoining the second-oldest cathedral in the Western Hemisphere is something special and it is. Hotel El Convento in a 350-year-old former Carmelite convent is the gold standard of historic hotels, with its high ceilings, handcrafted tiles, dramatic archways, wooden beams and views of San Juan and the bay from every room. Serafina Beach Hotel holds a special place for Borinqueños because it was the first new resort to open after Hurricane Maria. A sleek, swanky testament to the resiliency of the island, stylish locals flock to the pool on weekends to rent the pricy cabanas, get bottle service going and dance to international DJs. Opulent, modern and historic when it opened in 1919, the Condado Vanderbilt hosted Charles Lindbergh, Bob Hope and FDR as guests back in the day. It recently underwent a massive expansion and modernization and is presidential-worthy again today. If you’re more of the crunchy, meditating, kombucha-drinking type, the Dreamcatcher might be more aligned with your chakras. Small and chic with no TVs (amen), it’s billed as San Juan’s only vegetarian hotel. They offer yoga on the beach that conveniently is just steps away. If architecture is your thing, the Dream Inn PR’s design is striking. The 13-room guest house is built in a tropical modern-minimalist aesthetic that plays off the concrete vernacular style seen all over the city. The whole building is designed to highlight the interchange between light and shadow. The tranquil koi pond and rooftop lap pool are lovely.

Dreamcatcher

El Convento | Photo: Jose Ruiz Photography

Recommended hotels in San Juan

Hotels

- San Juan

There is nothing sexier than dancing salsa. The only question is, are you the lead? Or your partner?

Photo: Ardian Lumi

Things to do in San Juan

The centrepiece of historic Old San Juan is the legendary 500-year-old old fort, El Morro, which juts into the Atlantic. We recommend you take to the water in multiple vessels to get a better look at her. One option is an evening cruise on a replica of an 1812 schooner. You will feel very civilized as you learn about the centuries-old citadel whilst enjoying the balmy ocean breezes and sipping a cocktail. For the adrenaline junkies who prefer to captain their own crafts, try the jet ski tour. Go full throttle while taking in Old San Juan from the sea accompanied by your own tour guide/sea ranger. To learn more about San Juan, the third oldest European-established capital city in the Americas there is Museo de las Américas. Set in a former military barracks from the 1800s, the museum dedicated to Caribbean art and anthropology brings to life Puerto Rico’s pre-Columbian indigenous history and African heritage. One whole room pays homage to the island’s profound musical heritage. Another way to steep yourself in PR’s history is to steep yourself in its rum. Get your Drunk History on via a hands-on rum history course at Casa Bacardi. A short ferry ride from Old San Juan, the rum giant’s flagship factory offers three tours, all of which include rum tasting. We like the mixology class, which puts you behind the bar to master the mojito and two other classic rum cocktails. You’ll also learn where their iconic bat sign logo comes from.

We’re not saying it’s going to rain at all, not even one drop on your vacation, but if by any chance a wee sunshower happens to occur (which it won’t) there are a bunch of fun things to indoors. El Bastión is a cultural centre in a colonial building that offers a variety of walk-in activities such as aerial trapeze, capoeira, ballet, dance, and circus classes. There is nothing sexier than dancing salsa. The only question is, are you the lead? Or is your partner? Go find out at the dance academy. They offer bilingual classes in two ways—in Spanish and in English and on the one and the two. If you don’t know what that means, don’t worry. Your feet are in good hands at this dance school.

Recommended experiences in San Juan

Photo: Anders Wideskott

Things to see in San Juan

Let’s jump straight to the beach since we know you are trying to return home bronzeado. The gayest one in town is Atlantic Beach, which has some cool gay-friendly cafes and restaurants nearby. Balneario Escambrón is the city’s most picturesque playa. Protected by a coral reef, the sand is powdery and golden and you will likely find it quite uncrowded on weekdays. For more action, try Playa Isla Verde, the so-called Copacabana of Puerto Rico, which attracts attractive people who like to sun worship and play volleyball while their perfect bodies glisten in the sun. When you are satisfied with your base tan, spend a day wandering Old San Juan, the most beautifully preserved colonial centre in the Caribbean. Check out this DIY self-guided itinerary for a romantic tour. Break out of the tourist ghetto and go local at the Plaza Del Mercado in Santurce. The outdoor plaza is home to a farmer’s market and food vendors by day and by night turns into a rollicking block party with bars and cafes playing music and people dancing salsa everywhere. Go there and drink and sing and dance the night away at least once. Espacio 1414 is said to have one of the best private art collections in El Caribe. If you’re interested in bringing home a piece of contemporary art, or just want to browse, this is a place to do it. If you prefer your artwork al fresco, head to Calle Cerra, Ground Zero for street art in San Juan. In addition to the graffiti-inspired murals, the area also has scads of art galleries.

Photo: Tatiana Rodriguez

San Juan’s trailblazing food scene has been made official by the global arbiters of food

Where to eat in San Juan

San Juan’s trailblazing food scene has been made official by the global arbiters of food. Vianda was selected one of GQ’s Best New Restaurants in 2019 and names as one of the 20 Best New Restaurants by the James Beard Foundation. The husband-and-wife chef team are alumni of Blue Hill and their menu is diabolically and carnally mind-blowing with Caribbean, Thai, Indian, Spanish and Italian influences. Jose Enrique, a James Beard semi-finalist for best chef, opened a restaurant in what looks like someone’s nondescript house. There’s no sign, but you’ll recognize the place from the people queueing up outside to get in. The upscale Puerto Rican food is wow-worthy. Tostones, fried fish, mofongo, carne frita, and other criollo classics are completely true to what they are and served in the most perfect version of themselves. Don’t miss chic Santaella for an upscale, modern, world-inspired take on Puerto Rican food, aka comida criolla. Chef Jose Santaella has worked with some of the world’s most famous chefs including Ferran Adria of El Bulli and Eric Ripert of Le Bernadin. Consider starting off with the signature sandía mojito made with Puerto Rican white rum and mashed up watermelon. Then go for the goat cheese quesadilla appetizer followed by the shrimp in garlic cream sauce with plantain, yucca, and sweet-plantain mofongo. If you feel like getting glammed up for dinner, there is 1919 run by Michelin-starred Chef Juan José Cuevas in the posh Condado Vanderbilt Hotel. The refined fare is served impeccably in a chandeliered dining room with floor-to-ceiling views of the ocean. For more casual food, El Jibarito has been serving up abuela-inspired comfort food for half-a-century. Try the churrasco skirt steak. In the same category, but specializing in seafood is La Cueva del Mar. Yes, there’s a giant plastic marlin on the wall and a clock made from a ship’s steering wheel. So what? Just be quiet and eat the octopus salad with fried plantains and the fish tacos. Puerto Rico is known for its coffee, so do be sure to drink a lot of it while you’re there. Cuatro Sombras Coffee oversees every aspect of the bean supply chain, from farm to cup. The beans are roasted right in the shop. The coffee is so smooth, nutty and complex, you can drink it without sugar. The Casa Cortés Choco Bar is run by a fourth-generation family that’s been in the cocoa business since the Great Depression. Chocolate plays the starring role on the menu. Have your mind blown with the grilled cheese con chocolate, made of sharp cheddar and chocolate butter on a brioche. They will even deliver you a hot chocolate as you browse the art in the gallery upstairs. Sunday Drag Brunch is a new concept in PR and Latidos Restaurant is dishing it up big time so be sure and check it out.

1919

Shopping in San Juan

Puerto Rico is known for two types of folk crafts. Wooden carvings of Catholic saints called santos that islanders have been chiselling since shortly after Christoper Columbus landed ashore. And the terrifying but kinda-sorta cute vejigante papier-mâché masks worn at carnivals. These two crafts are special mementoes to take home. Puerto Rican Art & Crafts in Old San Juan is the best place to find both. It’s hard to stay looking sharp in tropical climes, but somehow all the cute Sanjuañeros manage to look impeccable nonetheless. Rock their look by shopping at the high-end Monsieur in Condado. Skip the Calvin Klein and head straight for the old-school guayaberas, those embroidered four-pocket linen shirts that Gary Cooper and John Wayne are rocking in this photo. A street-influenced label with panache, Root is a great place to shop for men’s clothing. They produce no more than 15 of each of their pieces, all of which are hand-crafted. If your style is more about minimalismo, Nono Maldonado, a former fashion editor at Esquire, has an unmatched collection of linen shirts perfect for the humidity. Skewing slightly younger is Otto, a shop that mixes tropical and classic prints with great success. Their clothes let you stand out without seeming like you’re desperately seeking attention.

Photo: Raoul Ortega

San Juan is the best place to be gay in the Caribbean

San Juan nightlife

San Juan is the best place to be gay in the Caribbean. The Condado and Santurce neighbourhoods are queer hangouts. The annual Puerto Rico Queer Filmfest takes place in November; Pride is in June. San Juan has the top nightlife scene en El Caribe, no contest. Circo’s Bar in Santurce is a blast, with famed drag shows, go-go dancers and karaoke nights. Sweaty, high-energy dancing to house and techno follows the shows. Open til dawn. Zal Si Puedes calls itself a gay ‘mini-bar’ because of its intimate setting and vibe. Nightly acts feature strippers, poets, singers and drag queens. If you’re lucky, you’ll show up on a night when Barbara Streisand or Donna Summer is performing. With lots of regulars and a crowd that skews older, the whole place has a homey, welcoming neighbourhood feel. Of the straight places to party, La Factoría was named one of the World’s 50 Best Bars and lauded by James Beard for its outstanding bar program. It’s a huge space containing separate rooms, each with a different theme including a mellow wine bar, a salsa club, and a Cuban speakeasy.

La Coctelera is another shrine to creative cocktails. Every ingredient is fresh and local from the liquor to the fruit juices to the syrups. The Tesla is made with vodka, limoncello, genever, lime, and tonic and served in a light bulb. The brand new Restaurante Chloé serves refreshing, tropical drinks that are sophisticated takes on the classics. The Peach Bliss is a mix of vodka, lime juice, peach nectar and ginger beer. La Respuesta is an artsy hotspot with stage shows and a hip-hop DJ spinning Latin trap, hip hop and reggaeton. You could just as easily catch a comedy show as a break dancing battle on any given night.