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Explore LGBTQ+ San Juan, Puerto Rico

One of the Friendliest Destinations in the Caribbean for LGBTQ+ Travelers

by Mark Chesnut
Credit Discover Puerto Rico

San Juan Pride kicks off the month on the first weekend in June with a parade, festival, and a variety of related parties and events.

(Photo by Discover Puerto Rico)

Puerto Rico has long been recognized as one of the friendliest destinations in the Caribbean for LGBTQ+ travelers, and that appeal continues to grow.

“Puerto Rico embraces diversity in every sense of the word; it’s built into our DNA as a destination,” said Leah Chandler, chief marketing officer at Discover Puerto Rico (discoverpuertorico.com), the destination’s tourism marketing organization. “The Island boasts a lively LGBTQ+ scene, with plenty of activities and attractions that promise a diverse and inclusive experience, ultimately earning us recognition as one of the top gay-friendly destinations in the Caribbean. In addition to offering an authentic cultural experience, we are convenient and hassle-free as a domestic destination. After all, there’s no currency exchange or passport needed for U.S. citizens, plus the LGBTQ+ community enjoys the same rights as those in the mainland United States, [including] anti-discrimination laws and same-sex marriage.”

Currently, San Juan is experiencing something of a boom in LGBTQ+ owned and gay-friendly businesses, as more investors recognize the destination’s growing potential. Travelers and locals alike are among the beneficiaries of the latest surge in growth.

Among the growing ranks of business owners is Stephan Watts, CEO and co-founder of Dreamers Welcome (dreamerswelcome.com), an LGBTQ+-owned hospitality group with a portfolio of more than 60 properties in Puerto Rico and North Carolina, as well Dreamcatcher, a 19-room hotel in San Juan’s popular Ocean Park neighborhood.

Stephan Watts and his business and life partner Roy Delgado of Dreamers Welcome (Photo by Dreamers Welcome)

Stephan Watts and his business and life partner Roy Delgado of Dreamers Welcome (Photo by Dreamers Welcome)

“Puerto Rico is known for its strong cultural identity and acceptance of diversity, which extends to the LGBTQ+ community,” said Watts, who’s lived in San Juan since 2013. “While there is still discrimination and homophobia, particularly among older generations and religious conservatives, younger generations are generally more accepting and open-minded. For a small island like Puerto Rico, the laws are more progressive than one might imagine. Puerto Rico has passed laws protecting LGBTQ+ individuals from discrimination in employment, housing, and public accommodations. In general, Puerto Ricans are simply friendly and caring people, and you get that sense the moment you step foot on the island.”

Another accommodation expert who’s bullish on San Juan is Tristan Schukraft, the founder of the telemedicine platform called MISTR who recently bought The Tryst, a 36-room hotel set on the city’s largest LGBTQ+ beach in the trendy Condado neighborhood. Schukraft also plans to renovate and reopen Circo, an LGBTQ+ nightclub he has also acquired that was once one of the city’s most popular dance clubs.

“Puerto Rico is s super gay-friendly destination,” said Schukraft, who envisions that the destination will become something like the Puerto Vallarta of the Caribbean. “The tourism board here is very active in promoting it as an LGBTQ destination. It has a lot to offer. It’s an island with dozens and dozens of beautiful beaches and it’s very welcoming.”

Couples Watching the Sunset (Photo by Discover Puerto Rico)

Couples Watching the Sunset (Photo by Discover Puerto Rico)

Top Attractions in San Juan
LGBTQ+ travelers are attracted to Puerto Rico’s capital for many reasons. The beaches in the neighborhoods of Condado and Ocean Park are especially popular, of course, but visitors looking to start their visit where the city began, way back in 1521, should head to Old San Juan, the beautifully maintained historic neighborhood that is a UNESCO World Heritage Site. This charming district is known for its well-preserved Spanish colonial architecture, pastel-colored buildings, and cobblestone streets, as well as an array of great restaurants and small hotels. Among the top sites are El Morro and San Cristobal forts, both remnants of the city’s colonial past.

There are lots of other places to explore in the San Juan metropolitan region, including the Bacardi distillery (200 PR-165, Cataño. Tel.: 787-788-8400. bacardi.com/us/en/casa-bacardi/tickets), which offers tours and rum tastings; the Museo de Arte de Puerto Rico (Puerto Rico Art Museum, 299 Avenida de Diego. Tel: 787-977-6277. mapr.org/es), which hosts an impressive array of art exhibits; and the bustling neighborhood called Santurce, which is home to vibrant street art as well as cool boutique shops and independent restaurants as well as La Placita, a market area that turns into a lively dining and entertainment zone after dark.

LGBTQ+ Life in San Juan
Travelers looking for an especially festive time to visit should plan their itineraries around San Juan Pride (pridepuertorico.com), one of two major annual pride events on the island (the other takes place on Puerto Rico’s west coast, later in the month). San Juan Pride kicks off the month on the first weekend in June with a parade, festival, and a variety of related parties and events.

This ever-growing celebration is a perfect example of the city’s diversity, according to Watts. “The LGBTQ+ community in San Juan has become more visible and accepted in recent years,” he said. “This is due in part to the efforts of local LGBTQ+ organizations and events like San Juan Pride, which draws thousands of people each year.”

If you can’t schedule a visit for pride, not to worry. You’ll find lots to do in San Juan, year round. “There has been an increase in the number and variety of LGBTQ+ venues in San Juan, including bars, clubs, and community centers,” according to Watts, who notes that there is still more work to be done. “It also has become more intersectional, with many people recognizing the connections between queer rights and other social justice issues. This has led to an increase in activism and advocacy, particularly around issues like police brutality and the island’s debt crisis. That said, there is still discrimination and violence against LGBTQ+ people, particularly transgender and gender nonconforming individuals. In addition, Puerto Rico’s conservative political climate and its relationship with the United States pose unique challenges to LGBTQ+ rights and representation.”

To make it easier for travelers to find businesses that celebrate diversity in San Juan, Discover Puerto Rico publishes an LGBTQ+ guide to the Island. (discoverpuertorico.com/things-to-do/lgbtq-travel).

No matter where you stay in San Juan, you’re never too far from a good bar. In Old San Juan, for example, La Sombrilla Rosa (154 C. de San Sebastián. Tel: 787-725-5656. facebook.com/people/La-SombrillaRosa/100054052796166) is a fun bar set in the heart of the historic district that hosts happy hours and exudes a laidback, friendly vibe that is perfect for relaxing with a drink after a day of touring the sites.

Condado Beach (by Dennis van de Water)

Condado Beach (by Dennis van de Water)

LGBTQ+ travelers are attracted to Puerto Rico’s capital for many reasons. The beaches in the neighborhoods of Condado and Ocean Park are especially popular, of course, but visitors looking to start their visit where the city began, way back in 1521, should head to Old San Juan.

The beachfront neighborhood of Condado, which is chock full of noteworthy hotels and restaurants as well as one of the most popular gay beaches, is home to Oasis Tapas & Lounge (6 Condado Avenue. Tel: 917-570-4787. facebook.com/oasiscondado), which is just a few steps from the part of Condado beach that’s most frequented by LGBTQ+ locals and visitors. Set in a space that dates back decades as an LGBTQ+ hangout, this is nice place for an after-beach drink, or perhaps a randy night out during its weekly Blackout Monday event, during which the lights are turned way down inside.

The adjacent neighborhood of Santurce doesn’t have a beach or as many hotels, but it does have the largest concentration of LGBTQ nightlife. A good place to start the evening is Tía Maria’s Liquor Store (326 Avenida José de Diego. Tel. 787-724-4011. facebook.com/TiaMariaSanturce), a venue with a misleading name that’s actually one of the city’s longest-running LGBTQ+ bars; it’s an old-school place with pool tables and a relaxed vibe.

For larger-scale dance clubs, top choices include Toxic Night Club (613 C. Condado. Tel: 939-422-3564. toxicnightclubpr.com), a popular venue that hosts drag shows and other events, and Kweens Club (1211 Av. Manuel Fernández Juncos. Tel: 787-481-3663. kweensklub.com), where the large dance floor gets packed every weekend and drag shows are also a common event.

Also popular, especially with gay men, is SX Club (Ponce de León Avenue. Tel. 787-532-4772. sxtheclub.net), a small but long-running venue with tiny dance floors and a large “men only” dark room.

Friendly go-go boys and great DJs add to the ambiance. Hotels in San Juan Puerto Rico’s capital offers a diverse array of accommodation styles. Among the LGBTQ+-owned options is Dreamcatcher (2009 Calle España. Tel: 787-455-8259. dreamerswelcome.com/dreamcatcher), a 19-room boutique property (billed as San Juan’s only vegetarian hotel) in the peaceful beachfront Ocean Park neighborhood.

Also in Ocean Park is Coqui del Mar (2218 C. Gral. del Valle. Tel: 939-428-9087. coquidelmar.com), a gay men’s guesthouse with comfortable accommodations, a small swimming pool, a large hot tub, and clothing-optional areas. The property is especially good for meeting other travelers, since it hosts day tours and events like Sober September Week, Transgender Takeover Week, and Bear Week, all of which feature a variety of programmed activities.

One of the newest names in the city’s LGBTQ+ hotel scene, meanwhile, actually has one of the longest histories in the community. The Tryst Beachfront Hotel (1 Calle Vendig. Tel: 787-965-5239. hoteltryst.com) is set in the former Atlantic Beach hotel, a property known for decades as the city’s top gay hotel. Located on the largest LGBTQ+ beach in the always-popular Condado neighborhood, The Tryst is undergoing a $6 million renovation and is home to The Wicked Lily (1 Calle Vendig. Tel. 787-965-5239. wickedlily.com) a beachfront restaurant that hosts a drag brunch every weekend.

Caribe Hilton (Photo by Hilton)

Caribe Hilton (Photo by Hilton)

Larger hotels in San Juan offer lots of noteworthy options, too. The Caribe Hilton (1 Calle San Gerónimo. Tel: 787-721-0303. caribehilton.com), for example, is a tropical mid-century oasis with its own beach and extensive amenities. Its lobby bar is one of two venues in San Juan that claims to be the birthplace of the piña colada, and the hotel restaurants are quite good.

Hilton, by the way, is in growth mode in Puerto Rico, with plans to double its presence on the island by 2025. Among its most recent brand debuts is the Condado Palm Inn San Juan, Tapestry Collection by Hilton (55 Condado Avenue. Tel: 787-721-9500. hilton.com), which opened in June 2023 as a rebranding of the former Best Western Plus Condado Palm Inn. The 186-room property has two restaurants, two swimming pools, and a dedicated beach area at Condado Beach, which is just a block away.

The Condado Plaza Hotel (999 Ashford Ave. Tel: 787-721-1000. hilton.com) meanwhile, is slated to undergo major renovations and will be relaunched in 2025 as two hotels within the Hilton portfolio: the 332- room San Juan Condado Plaza, Curio Collection by Hilton, set in an attractive building that dates to 1963 and was designed by famed architect Morris Lapidus, and the 240-room Hilton Garden Inn San Juan Condado, located within a separate mid-century building.

A few blocks down Ashford Avenue lies another mid-century-modern gem: La Concha Renaissance San Juan Resort (1077 Ashford Ave. Tel: 787-721-7500. marriott.com) a property known for its iconic, seashell-shaped architectural element that once housed a restaurant. This decidedly hip hotel, which has a lively lobby bar, is undergoing a $45 million renovation that will ultimately see it rebranded as part of Marriott International’s Autograph Collection.

Drag Brunch The Tryst (Photo by The Tryst)

Drag Brunch The Tryst (Photo by The Tryst)

Nearby, the Condado Vanderbilt Hotel (1055 Ashford Ave. Tel: 787-721-5500. condadovanderbilt.com), a member of Preferred Hotels & Resorts, is an ideal choice for anyone in the mood for classic luxury. The hotel’s history goes back to 1919 and its historic roster of guests is indeed noteworthy.

Also in Condado is the San Juan Marriott Resort and Stellaris Casino (1309 Ashford Ave. Tel: 888-817-2033. marriott.com), which recently benefited from a $20 million renovation and is known for its multiple dining options and sizeable casino.

An extensive renovation has also brought new sheen to the Doubletree by Hilton San Juan (105 Ave. de Diego. Tel: 877-926-3030. hilton.com), an attractive urban resort with a lush pool area; it’s an ideal location for visitors looking to explore the hip shops and restaurants on nearby Loiza Street.

Shopping and Dining San Juan is heaven for foodies and shopaholics, and Condado’s Ashford Avenue is a hotspot for both. You can shop for designer brands like Cartier (1054 Ashford Ave. Tel: 787-721-5879. stores.cartier.com), as well as cool clothing at Root (1129 Ashford Ave. Tel: 787-946-7668. shopatroot.com).

Art lovers, meanwhile, may want to consider taking home original artwork and crafts from the island. Top galleries include the Pamil Fine Art Gallery (1897 Glasgow St. Tel: 787-366-7963. pamil.com), which specializes in contemporary art, and Galería Botello (208 Calle del Cristo. Tel: 787-723-9987. botello.com), which is housed in a 350-year-old building in Old San Juan and sells sculpture, paintings, and other works by a variety of artists.

The hip-and-happening Calle Loiza is another popular place for LGBTQ+ travelers in search of stylish shopping. Electroshock (1811 Calle Loiza. Tel: 787-727-5428. facebook.com/electroshockxchange) is the place for ultra-cool vintage clothing and one-of-a-kind retro décor, while Playero Surf Shop (1604 Calle Loiza. Tel: 787-723- 2242. playero.com) is a great place to pick up beach and surf wear from one of the island’s most beloved brands.

Shoppers can satisfy their mall fix at Plaza las Américas (525 Roosevelt Ave. Tel: 787-767-1525. plazalasamericas.com), one of the island’s largest shopping complexes, and at the Mall of San Juan (1000 The Mall of San Juan, Blvd. Tel: 787-759-6310. themallofsanjuan.com/), a newer mall that’s filled with upscale retailers including Boss, Bvlgari, Coach, Gucci, and Guess. Among the local designers with space at the Mall of San Juan is Luis Antonio (Ave. De Diego 408, Suite 1. Tel: 787-634-0024. luisantoniomoda.com), who has dressed celebrities including Jennifer Lopez, Demi Lovato, and Carrie Underwood, to name a few. He creates fresh looks for both men and women, and his spring 2024 is the result of a collaboration with former Miss Puerto Rico 2018 Kiara Liz.

Gay couple in Old San Juan (Photo by Discover Puerto Rico)

Gay couple in Old San Juan (Photo by Discover Puerto Rico)

Excellent dining options run the gamut from luxurious and expensive to cheap and delicious. At the higher end is 1919 (1055 Ashford Ave. Tel: 787-721-5500. condadovanderbilt.com/dine/1919-restaurant), which is located at the Condado Vanderbilt and headed by Michelin-starred Executive Chef Juan José Cuevas. Another upscale favorite is Mario Pagan (1110 Magdalena Ave. Tel: 787-522-6444. mariopaganrest.com), where the menu showcases Puerto Rican and international favorites.

La Placita de Santurce, a section of the Santurce neighborhood known for its daytime market and after-dark dining and drinking scene, is a popular and rewarding place for discovering new culinary delights. One of the top places at La Placita for foodies is Santaella (219 Calle Canals. Tel: 787-725-1611. josesantaella.com), where “Puerto Rican nouvelle” cuisine is the delicious focus of Chef Jose Santaella. Dishes include oriental salmon filet, crisp whole fresh red snapper, and boneless chicken in creole stew.

Old San Juan is another hotspot for culinary excellence. Among the most recognized venues is Marmalade (317 Fortaleza St. Tel: 787-724-3969. marmaladepr.com), a beautiful restaurant and wine bar where Chef Peter Schintler oversees a stunning, five-course tasting menu that’s available with wine pairing. The five-course option is available for groups of five people or less; larger groups can reserve space for a seasonal, 14-course offering.

For deliciously traditional Puerto Rican cuisine at a more accessible price, head to Orozco’s (1126 Ashford Ave. Tel: 787-721-7669. orozcosrestaurant.com), which Guy Fieri featured in his TV show, Diners, Drive-Ins and Dives.

Mofongo at Orozco's (Photo by DepartureLevel.com)

Mofongo at Orozco’s (Photo by DepartureLevel.com)

Also noteworthy and reasonably priced is Lote 23 (1552 Ave. Ponce de León. Tel: 787-223-4984. lote23.com), an open-air “gastronomic park” not far from most of the city’s LGBTQ+ bars that hosts an array of interesting culinary vendors. You’ll find treats ranging from Mexican street food at Mister Flautas, to creative Caribbean cuisine at Pa’l Cilantro, to Puerto Rico’s take on Chicago-style deep dish pizza at Deep Dish PR). And at Kasalta (1966 Calle McLeary. Tel: 787-727-7340. kasalta.com) you can walk (and dine) in the footsteps of Barack Obama; he’s among the patrons who’ve savored the restaurant’s delectable Caribbean cuisine, which includes Cuban sandwiches and Spanish Mallorcas.

One thing is for sure: you won’t go hungry in San Juan.

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