San Juan Travel Guide Travel Guides > Puerto Rico > San Juan Suzi SiegelThree 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!” Fancy a trip? Save yourself days of research by having us plan it for you. Discover Trip Design Hotels Things to do Things to see Food & Drink Shopping Nightlife Trip Design Serafina Beach Hotel, the first new resort to open after Hurricane Maria, is a sleek, swanky testament to the resiliency of the islandThe best hotels in San JuanYou 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. DreamcatcheriRecommended hotels in San Juan Hotels - San Juan Hotel El Convento This hotel is located in the heart of historic Old San Juan. Hotel guests receive beach privileges at the El Convento Beach Club on Isla Verde Beach. Book on Booking.com Hotels - San Juan The Dreamcatcher The Dreamcatcher is located on the beach in the gated community of Ocean Park. This vegetarian property offers on-site yoga and meditation classes. Free WiFi is available. Book on Booking.com Hotels - San Juan Condado Vanderbilt Hotel This oceanfront hotel offers an outdoor pool and a spa and wellness centre and is located a stone’s throw away from the Condado Lagoon. Free WiFi access is available in all areas. Book on Booking.com Hotels - San Juan Serafina Beach Hotel Serafina Beach Hotel boasts an outdoor swimming pool, a fitness centre, and a terrace. Mediterranean and Italian dishes are served at the in-house restaurant. Book on Booking.com Hotels - San Juan Dream Inn PR Dream Inn PR is located a 5 minutes’ walk from Barbosa Park and Ocean Park Beach. It features a swimming pool and a beautiful indoor fountain. Book on Booking.com Hotels - San Juan O:Live Boutique Hotel Located in the exclusive Condado neighbourhood, O:Live Boutique Hotel has a Mediterranean décor and stylish suites that include a luxurious rain shower with hydromassage jets. Book on Booking.com Hotels - San Juan The Gallery Inn The Gallery Inn, located less than one kilometre from San Juan National Historic Site, features uniquely decorated rooms. It offers Atlantic Ocean views, an outdoor swimming pool and Wi-Fi. Book on Booking.com Explore more places to stay like this in San Juan View on Booking.comPowered by Booking.com El Convento | Photo: Jose Ruiz Photography There is nothing sexier than dancing salsa. The only question is, are you the lead? Or your partner? Photo: Ardian LumiThings to do in San JuanThe 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. iRecommended experiences in San Juan Experiences - San Juan Bacardi Distillery Tour and Old San Juan 4.5 hours Experiences - San Juan From Fajardo: Full-Day Culebra Islands Catamaran Tour 7 hours Experiences - San Juan Old San Juan Walking & Tasting Tour 3 hours Experiences - San Juan El Yunque Rainforest and Luquillo Beach Tour 7.5 hours Experiences - San Juan From San Juan: Horse Riding at a Private Ranch 2 hours Explore more experiences like this in San Juan Book on GetYourGuide.comPowered by GetYourGuide Photo: Anders Wideskott Going to San Juan? The same team that brings you the content you love designs your perfect tripWhat to see in San JuanLet’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 foodWhere to eat in San JuanSan 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 1919Shopping in San JuanPuerto 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 CaribbeanSan Juan nightlifeSan 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. La RespuestaMain image courtesy of E.P. Anderson Studios. Custom Trip PlanningGo on that fabulous vacation you deserve even when you lack time to plan it yourselfFrom $35 Plan my trip Special SelectionExclusive Mr Hudson offersOut now from gestaltenMr Hudson Explores Browse the Book share Condado Vanderbilt Photo: Natalya Casa Bacardi 1919 Museo de las Americas Photo: Robert V. Ruggiero El Bastion Condado Beach La Respuesta Photo: Tatiana RodriguezDid you enjoy this article? Then sign up for our newsletterDid you enjoy this article? The same team that curates our content designs your perfect trip Explore more The best gay-friendly places to stay in Puerto RicoPuerto Rico is a Caribbean world in miniature. An intriguing Spanish-American colonial heritage meets sparkling seas, secluded beaches, and a forested interior rich in wildlife. Read story > The best gay bars in OrlandoOrlando is the tenth gayest city in the US percentage wise and its gay nightlife and gay bar scene is a testament to that fact. Read story > Hotel Alexandra - exquisite Danish design in CopenhagenCopenhagen’s Hotel Alexandra is a wonderful and unique destination that falls into a category somewhere between a boutique hotel and design museum. Everywhere you turn, there’s an original piece of mid-century Danish design history. Read story > Subscribe to our newsletterYou can unsubscribe at any time by clicking the link in the footer of our emails. We use Mailchimp as our marketing platform. By clicking below to subscribe, you acknowledge that your information will be transferred to Mailchimp for processing. CookiesWe use cookies to offer you a better experience. By continuing to use this website, you consent to the use of cookies in accordance with our Cookie Policy.Accept