Puerto Rico Gay and Lesbian Vacations

Puerto Rico

Puerto Rico

Your gay Puerto Rico vacation

Looking more like a lush province of Spain than an American territory, Puerto Rico is one of the most foreign experiences you can have in the U.S. And it’s one of the gayest vacation experiences in all the Caribbean. Most of Puerto Rico’s gay and lesbian infrastructure is found in the Old City of San Juan, a colonial, walled city within a city. And despite traditional influences, gays and lesbians have more legal rights here than in many U.S. states.

Best in Stay

LGBT Best in Stay Puerto Rico hotels

From $189

La Concha Renaissance Resort

4 stars
4.3 / 5 683 reviews

San Juan, Puerto Rico

Rate includes breakfast

La Concha Renaissance Resort in San Juan offers a sophisticated, chic atmosphere as well as luxurious guest rooms with state-of-the-art amenities and furnishings. In addition, the resort features a casino, an on-site fitness center, and relaxing spa treatment options. The hotel's accommodations consistently rank highly... More

From $219

Marriott San Juan Resort and Stellaris Casino

4 stars
4.2 / 5 943 reviews

San Juan, Puerto Rico

Rate includes breakfast

Four diamond extravagance is offered to all guests at the Marriot San Juan Resort, keeping adults entertained with champagne-style pleasure, while wowing kids with games and waterslides. An oasis among Puerto Rico's party atmosphere, the hotel features grand architecture, neutral decor, surrounding vistas and tall palm... More

From $104

At Wind Chimes Boutique Hotel

3 stars
3.5 / 5 69 reviews

San Juan, Puerto Rico

At Wind Chimes Inn is a lovingly restored Spanish villa with a bright white exterior and terra cotta roof. The boutique inn's lush, walled garden leads into the entrance hall decorated with local art. Rooms have light-colored furniture and bright sunflower-printed bedspreads. A 28-foot tiki bar, built to resemble a sail... More

From $175

Hotel El Convento

4 stars
4.5 / 5 184 reviews

San Juan, Puerto Rico

SAVE 10%

With a wealth of history, rustic decor and charming details, it's easy to see why Hotel El Convento was chosen by Condo Nast Traveler as one of the 'Top 10 Hotels in the Caribbean'. Situated in Old San Juan, this boutique luxury hotel makes guests feel equally relaxed and spoiled. With the daily manager's reception... More

From $166

Blue Horizon Boutique Resort

3 stars
4.1 / 5 19 reviews

Vieques, Puerto Rico

Blue Horizon Boutique Resort stirs the romance of the Spanish Virgin Islands with a historic setting on the grounds of a former sugar plantation great house. The property, a collection of villas and rooms overlooking the Caribbean, maintains the period charm with antique-filled spaces and eclectic artwork. Guests retreat... More

From $249

The Ritz-Carlton, San Juan

5 stars
4.4 / 5 411 reviews

San Juan, Puerto Rico

Immerse yourself in total luxury and relaxation at The Ritz Carlton, San Juan, with two miles of sandy beaches to enjoy. Modern and sophisticated decor makes the 416 rooms both stylish and comfortable. Spa treatments include The Ritz Carlton Signature Massage and Sea Body Wrap, and you can take a dip with the kids in the... More

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Departure Arrival Travel dates Round-trip
Orlando San Juan Wed, Aug 26 - Sun, Aug 30 $244
Orlando Aguadilla, Isabela Tue, Sep 22 - Wed, Sep 30 $247
San Juan Vieques Wed, Dec 9 - Mon, Dec 14 $238
Orlando Ponce, Guanica Thu, Sep 10 - Sun, Sep 20 $250
Chicago Mayaguez, Cabo Rojo Wed, Aug 12 - Sat, Aug 15 $102
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  • Miss Richfield 1981 says it best in this video—not all travel sites are created equal. When you book on Orbitz, your travel dollars work harder. Here’s why:  

    • We’re the ONLY leading travel agency with a perfect Corporate Equality Index Score from the Human Rights Campaign, with two GLAAD Media awards to boot.
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  • Puerto Rico nightlife

    In the elegant Condado section and the more industrial Santurce area, a selection of LGBT clubs and bars pump into the night. There’s even a lesbian bar cheekily named Cups. Condado Beach can be filled with gays and lesbians, as well as nearby Ocean Park Beach.

    LGBT events

    A big Pride-style party called Inferno happens over Memorial Day weekend, and fun events like bear get-togethers, drag shows and pool parties happen throughout the year.

    Exploring Puerto Rico

    You can explore the verdant central mountains and their pretty villages and coffee plantations, where English is barely spoken. Puerto Rico has nearly twenty forest preserves, where visitors can hike or picnic. And there’s the mellow adjacent isle of Vieques just off Puerto Rico’s northeast coast, popular with queer tourists and retirees.

  • Winter and spring are high-priced seasons

    From mid-December to mid-April, snowbird tourists fleeing from cold northern climates flock to Puerto Rico. Temperatures year-round have a relatively small range from 75°F to 85°F, but August can be the hottest and wettest month.

    Driving is a pain in San Juan

    Filled with narrow cobblestone streets made for horse carriages, opt instead for taxis or tourist shuttles.

    Head to the Old City for creative dining

    Although Puerto Rico does not have a signature cuisine, the section of the Old City called SoFo or South of Fortaleza is brimming with cool restaurants serving creative fusion cuisine in hip eateries.

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