Featured Gay Friendly Hotels in San Juan

Gay San Juan

San Juan is the capital of Puerto Rico and the oldest Caribbean city to fly the American Flag. The island of Puerto Rico has long been a popular destination for east coast and Midwestern visitors. As more and more people from out west have taken Caribbean cruises, they have discovered the unique charm, beauty, and excitement of this beautiful island and it’s warm and friendly people.

San Juan is divided into “old” and “new” cities. The capital city was initially founded in the 16th century by Spanish colonists until it was eventually incorporated to be part of the United States after the Spanish-American War. Even without full statehood, it’s an important part of the American identity. Most of San Juan's tourism is in the Old Town, though many of the hotels and beaches are located in the new part of San Juan. That's where you'll find the famed Condado Beach, Ocean Park, and Santurce districts popular with tourists. Home not only to numerous gay guest houses, bars, discos and restaurants, it's also the center of tourist nightlife and the location of the best hotels and casinos on the island. Ashford Avenue is the main thoroughfare and takes you to Dos Hermanos Bridge, which leads into “old” San Juan. 

San Juan Gay Scene

San Juan is generally regarded as one of hte most LGBTQ welcoming destinations in all of the Caribbean. There are numerous gay bars and clubs, and the gay scene in San Juan is thriving with both tourists and locals. There is even a gay-owned and opererated hotel, the Coqui del Mar, which hosts annual LGBTQ festivals and events like a Naked Gay Weekend in the summer, and a Winter Pride Fest every December. San Juan's annual pride festival, San Juan Pride, is a weekend of parties, special events, and shows each year during June's first weekend.

Most of San Juan's gay scene is located along Calle Condado where you'll find several bars and clubs within walking distance.

When to Visit

Though most tourists visit Puerto Rico over the winter season (December to February) to avoid winter weather in North America, the shoulder seasons between April and June are equally enticing for tourism. There are fewer tourists but it's before the rainy season starts. Another advantage of visiting in the spring and early summer is that hotels will be cheaper and you can get better deals on most tourist activities.

It's important to be mindful of hurricane season in Puerto Rico, especially considering the devastating effects of Hurricane Maria in 2017. For those reasons, avoid hurricane season which begins in late summer and runs up until late October or early November. If you do travel during that period, be prepared for last-minute travel delays or necessary changes in your itinerary like most other Caribbean destinations.

San Juan Gay-Friendly Activities & Attractions

Old San Juan is a seven square block area that was once completely walled and had been constructed as a military stronghold. Walking through the area, you’ll want to visit the fortress of San Felipe Del Morro, The Museum of Art & History, the Pablo Casals Museum, Plaza De San Jose, and site of San Jose Church, the 2nd oldest in the Western Hemisphere, La Foreteleza, the governor’s mansion as well as El Arsenal. There is so much to see in this historic area, a first stop should be The Tourist Information Center, 301 San Justo Street or at City Hall on the Plaza de Armas for free brochures and walking tour maps. 

San Juan Gay-Friendly Dining

El Jibarito

Located in Old San Juan, El Jibarito is a casual restaurant and very local—just off a main road but easy to find. It's popular with locals who come in regularly for the great food at a reasonable price. It can get very crowded in the evenings during dinner time, so consider visiting around the dinner rush time. Inside, the atmosphere is very casual and sometimes your meal might feel rushed, but just enjoy the buzz of the locals and servers. On the menu, you’ll find classic dishes like mofongo, plantains, and even a Christmas special dish available year-round.

Punto de Vista Rooftop Restaurant

Located on the rooftop of Hotel Milano in Old San Juan, the Punto de Vista rooftop bar and restaurant is a favorite for tourists because of its great Bacardi happy hour deals and it's incredible views over the San Juan skyline. The menu includes authentic Puerto Rican comfort food & happy hours. The real appeal are the drinks, and be warned: it gets very busy! You can stop in at the entrance to the hotel to make reservations for later the same day, which will help guarantee a table during the busy sunset hour.

La Casita Blanca

One of the loveliest restaurants in San Juan, La Casita is located outside of Old San Juan but is easy to reach via Uber or taxi. The restaurant is located in a house with a beautiful garden terrace and a casual interior full of bric-a-brac and charming decorations. It looks like you're eating at your grandmother's house! The menu features all the traditional Puerto Rican dishes, including many seafood specialities. The sweetness and charm of the restaurant isn't just in the design though, servers are happy to offer up complimentary appetizers to every guest.

San Juan Gay-friendly Bars & Nightlife

Circo Bar

One of San Juan's best gay bars, it's fun for both a casual evening cocktail bar or a raging dance party at night. While it's nice in the early yevenings, the party really gets going in the early morning hours. Come for the music, but stay for the cute boys (and go-go dancers)! As the biggest gay club in Puerto Rico, it pretty much attracts everyone—local and tourist—at least once over each weekend.

Coqui del Mar

Located in the Ocean Park neighborhood of San Juan, the Coqui del Mar guest house is a gay-owned hotel with a clothing-optional pool. In addition to the gay hotel amenities, the property hosts special events and parties throughout the year, so if you're looking for a fun gay weekend, it's worth checking their calendar in case they're hosting any events durinig your trip

Safety

Due to extreme parking problems in San Juan, the use of taxis are recommended. A word of caution, though, please take metered cabs only and insist that the meter be on.

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