Even before Puerto Ricans claimed fame to illustrious homo-sexpot, Ricky Martin, drag superstar, Jessica Wild, and a record five winners of the Miss Universe Pageant, their unwavering pride for their homeland was unmistakable. Regardless of political domination by the Spanish empire or the U.S. Empire, Puerto Ricans have developed a distinctive yet evolving national identity, commingling pre-Hispanic roots and Spanish conquest with Afro-Caribbean flavors and American commercialism. Puerto Ricans affectionately and proudly refer to themselves as Boricua, a modern linguistic derivation of Boriken, the island’s original, pre-Hispanic Taíno name. Nowadays, Puerto Rican pride goes beyond frilly flags hanging from the rear view mirror, Raggaeton shout-outs and NYC parades – it’s an ongoing social and cultural revolution happening on the island itself.

Puerto Rico’s capital, San Juan, plays a key role as the Caribbean’s only true gay ambassador and thriving metropolis. While battles for GLBT rights have met great success in Europe, Mexico, and Argentina, in 2010 Puerto Rico remains the only Caribbean island embracing a same-sex lifestyle. This tropical maverick also differentiates itself from its counterparts by offering much more than hair braiding, barefoot escapades, beautiful beaches and Rastafarian rhapsody. San Juan, in particular, offers first-class cultural opportunities, big city sophistication, and some of the best-preserved colonial architecture in the Americas.

Seductive beaches notwithstanding, Castillo San Felipe del Morro is San Juan’s centerpiece monument. Rising 145 feet from the sea with 18-foot-thick walls, the 70-acre enclave impresses from all angles. El Paseo de la Princesa (which literally translates to the Princess’ Promenade…) wraps around the ancient city walls of the neighborhood now known as Old San Juan. This yellow brick road leads you toward an expansive gateway that reveals El Morro in a panorama of fairy tale proportions. The fascinating staircases and mazes of the castle grounds lead to windswept precipices and eerie dead ends. The Hogwarts magic continues at the opposite end of Old San Juan at El Morro’s counterpart, Castillo San Cristobal. The well-preserved cobblestone streets of Old San Juan host over 400 meticulously restored 16th- and 17th-century Spanish colonial buildings alongside charming plazas, old school banquet halls, and the cheesy Hard Rock-like joints near the cruise ship port. The old city’s hottest restaurants reside at the southern end of Fortaleza Street, also known as SoFo. Ten years strong and trendy, the Asian-inspired Dragonfly (www.oofrestaurants. com) still attracts the San Juan glamorpuss for Latin American-Asian fusion fun in the ghetto-fabulous re-creation of an Asian opium den.

Though less pristine than Vieques’ downy sands, San Juan’s beaches are spicy, gregarious and seductive. The city has two gay beaches – one in front of the gay Atlantic Beach Hotel (www.atlanticbeachhotel. com) in the high-rise Condado district (at end of Calle Vendig), and the other opposite Pamela’s Caribbean Cuisine in the low-rise Ocean Park district (between Calle Taft and Calle Santa Ana). The Atlantic Beach Hotel is a downright dump, but it does boast an awesome beachfront bar, perfect for enjoying fruity cocktails in the birthplace of Piña Coladas. A close cab ride away, Loiza's Piñones sector showcases Puerto Rico’s raw beach beauty at its finest. Within the spectacular Bosque Estatal de Piñones (along Highway 187 between San Juan and Loíza) lies an ecological treasure chest of uninhabited beaches, mangroves, salt flats, lagoons, and rich bird life.

After your play date with nature, well-deserved calories await at the global awardwinning Pikayo (www.pikayo.com), maintaining the crown as Puerto Rico’s superlative dining option for 20 years, with a recent re-location to the Conrad Condado Plaza. Post suppertime, crowds swarm the roof-top bar of the Water & Beach Club Hotel before heading to traditional nighttime staples like the video bar, Circo (www.circobar. com), and dance palladium Krash Klub (www.krashpr.com).

While gay life centralizes in residential Condado, more ideal options for accommodation are found in nearby Isla Verde. This is where Vegas meets the beach, and the ubiquitous vacation vibe keeps things uncomplicated. In this resort- heavy district, the Ritz-Carlton, San Juan Hotel, Spa and Casino (www.ritzcarlton.com) stands out among the competition, combining all the splendor of a Ritz with the simplicity of the tropics. A tropical elegance motif unites the vast spaces of the oceanfront sanctuary. In common areas, grand pineapple chandeliers shine upon fresh exotic floral arrangements while lush reds and greens contrast the teak furniture in guestrooms. Bathroom queens will love the property’s “Water Closet” extravaganza. The palatial bathtub, shower, toilet, and vanity area each merit unique space, together comprising a square footage larger than a NYC apartment. The beach chairs, umbrellas, table service, and beachfront pampering are yours for the taking. However, the marble lion-clad, five-in-one 7,200 square foot swimming pool emerges as the resort’s center of attention (though resident iguana George would like to think it’s him). Whether sipping margaritas by the pool, getting carried away at the hotel spa, or watching the waves crash from the Club Level balcony, the hotel fosters an unabashed haven for relaxation, romance, and self-indulgence.