The third-largest city in the Caribbean, with a metro population of around 2.1 million, diverse and dynamic San Juan, Puerto Rico also ranks among the region's top gay tropical vacation destinations (the offshore Puerto Rico island of Vieques is another LGBT hot spot). Indeed, tourism plays a vital role in this culturally vibrant city with miles of beautifully kept white-sand beaches, a small but energetic gay club scene, a wealth of both informal and sophisticated first-rate restaurants, and one of the greatest Colonial-era neighborhoods in the Western Hemisphere, Old San Juan, which is also home to one of the most popular cruise-ship ports in the Caribbean.
Mainstream Resorts in San Juan
San Juan is home to a number of larger resort hotels, including a mix of mid-rise properties and sprawling beach compounds that dot the city's shoreline, with the greatest concentrations in Isla Verde Beach (near the airport, but thankfully not in the flight path) and Condado and Miramar (centrally located and close to downtown), with a number of mostly smaller boutique properties set amid the cobbled streets of historic San Juan, which is about a 15- to 20-minute drive from downtown. These mainstream hotels include reliable mid-priced to upscale chains like Sheraton, Marriott, and Hilton as well as some higher-end brands, such as Ritz-Carlton and Inter-Continental, and some luxury independent hotels - notably the Condado Vanderbilt Hotel and the Hotel El Convento. Although compared with other Caribbean vacation destinations, San Juan offers a pretty good value, and you can find some excellent deals even at these top-of-the-line hotels.
Guest Houses and Boutique Inn in San Juan
San Juan also has a number of smaller properties, many with fewer than 10 rooms, and some of these with very strong followings among LGBT visitors. The aforementioned Old San Juan neighborhood contains many of a few of these more intimate accommodations, as does the eastern, more residential section of the Condado district and, a bit farther east and even more residential (and relaxed), the pretty Ocean Park neighborhood.
Here's a more detailed look at a few of the top gay-friendly accommodations in San Juan.
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Set on sheltered lagoon as well as a gorgeous section of oceanfront right by the bridge to Old San Juan, and containing 571 rooms and suites set among two buildings, the stylish mid-century modern Condado Plaza Hilton (999 Ashford Ave., San Juan, 787-721-1000) is a perfect roost if you're seeking proximity to recreational activities and plenty of on-site restaurant choices. Rooms are done in bright, lively color schemes and have floor-to-ceiling windows, private balconies, and mini-refrigerators. The nine dining options include the acclaimed restaurant, Pikayo (the domain of San Juan celeb chef Wilo Benet), and other resort amenities include bike rentals, a fitness center, kayak and other boat rentals, tennis, and beautiful swimming pools.
The Condado Plaza has been one of the most prominent in San Juan in terms of welcoming LGBT travelers. In fact, through June 2017, the hotel is offering a terrific package geared to same-sex couples looking to celebrates their first wedding anniversary in style. The Coloring San Juan With Love package comes with a $275/nightly price tag and includes welcome drinks in the trendy Eternal Lounge, turn-down service, an amazing multi-course feast for two at Pikayo restaurant, full breakfast each morning, and an LGBT itinerary and guide to San Juan written by gay travel expert Andrew Collins (the author of this guide and producer of this website). Note that this package has a three-night minimum-stay requirement.
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The LGBT-owned Andalucia Guest House (2011 Calle McLeary, San Juan, 787-728-7838) is a charming eight-room inn just four blocks from the beachfront in relaxing Ocean Park and on a street a handful of good restaurants (there are also some very nice places to dine along the beach). The handsome inn is decorated with a Moorish and Andalusian flare that's reflected in its name, and all rooms have private baths, simple but attractive furniture, a/c and ceiling fans, and satellite TV. There's a sundeck that's ideal for relaxing on warm mornings as well as a cloistered patio with a Jacuzzi tub. Rates start around $100 in high season, and it doesn't cost much more for the largest studio room, with a kitchen and two queen beds. This is a great little find and a nice value.
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The exceedingly inviting and beautifully appointed Numero Uno Guest House (1 Calle Santa Ana, San Juan, 787-726-5010) is, as the name might suggest, truly one of the top accommodations in San Juan - it fills up quickly in high season, so book ahead if possible. The small, modern boutique hotel has just 14 rooms and is situated on Condado Beach. It's also home to the excellent little restaurant, Pamela's Caribbean Cuisine, which turns out creative and contemporary island fare and has seating overlooking the ocean. Rooms are simple, uncluttered, and artfully decorated and include some very economical options. Many guests, however, find that It's worth spending a bit more for one of the ocean view rooms (these typically run about $30 more per night than a standard room overlooking the garden) - the views out over the Atlantic are lovely. Or, for the ultimate splurge, book the two-bedroom, two-bath penthouse on its own floor, and with amazing ocean views, a fully stocked kitchen, a private veranda, high pitched ceilings, and lots of space to spread out. It's also a great option for two couples.