San Juan Gay-Friendly Activities & Attractions 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. For those reasons, avoid hurricane season which begins in late summer and runs up until late October or early November. It's important to be mindful of hurricane season in Puerto Rico, especially considering the devastating effects of Hurricane Maria in 2017. 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. There are fewer tourists but it's before the rainy season starts. 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. Most of San Juan's gay scene is located along Calle Condado where you'll find several bars and clubs within walking distance. 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. 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. There are numerous gay bars and clubs, and the gay scene in San Juan is thriving with both tourists and locals. San Juan is generally regarded as one of hte most LGBTQ welcoming destinations in all of the Caribbean.
Ashford Avenue is the main thoroughfare and takes you to Dos Hermanos Bridge, which leads into “old” San Juan. 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. That's where you'll find the famed Condado Beach, Ocean Park, and Santurce districts popular with tourists. 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.
Even without full statehood, it’s an important part of the American identity. 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.
San Juan is divided into “old” and “new” cities. 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 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.