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A gay-friendly U.S. commonwealth

San Juan, Puerto Rico may just be the solution to the next argument a gay couple could have over where to vacation. Let's imagine the scenario - Jane may want to go some place foreign and exotic, but Joan would rather stay on U.S. soil. Jim has his heart set on a tropical-island getaway, while John is insistent on going somewhere with an urban edge. You both prefer a place with a gay social scene, but it doesn't have to be circuit-party central. San Juan may be the only city in the world that satisfies all of the aforementioned criteria."

In this sultry, waterfront city of 1.5 million, it's hard not to feel you're in a foreign country - it's many times farther from southeastern Florida than either Cuba or the Bahamas, and the music, language, cuisine, architecture, and social customs borrow from both indigenous tribes of the Caribbean and the island's former overlord, Spain. Yet English is widely spoken, U.S. dollars are used, and placing phone calls or mailing letters costs the same as it does back on the mainland. The United States assumed control of the island following the Spanish-American War in 1898 - officially, Puerto Rico is a U.S. commonwealth, and a quite gay-friendly one at that.

San Juan has appealing accommodations all along its shoreline, but the Condado Beach district has the most visible gay scene. The Atlantic Beach Hotel is a key social hub. Rooms are basic and perfectly clean, and many have marvelous views of the ocean and of the ever-popular open-air gay bar downstairs. The Sunday T-dance here is de rigeur for lesbian and gay revelers, but there's fun stuff going on most nights, especially at happy hour. A more basic lodging option is the economical Condado Inn, which has a laid-back gay cocktail bar. For socializing, also keep in mind Junior's, a low-keyed neighborhood bar that usually has strippers.

It's mainstream, but Condado's El Canario by the Sea makes for a more charming overnight. This intimate 25-room hotel has dapper, brightly appointed rooms and a lush courtyard where Continental breakfast is served. The beautifully situated 650-room Caribe Hilton recently underwent a multimillion-dollar renovation. It has a full-service spa, excellent restaurants, and several oceanfront swimming pools. Try to dine at least once at the Escambron Beach Club, which might prepare the freshest Puerto Rican seafood around. Here you can savor delicious octopus-and-conch salad, plus tender steaks, fried plantains, and garlic chicken. It's along the beach, almost behind the Hilton.

Just east of Condado lies the residential and exclusive Ocean Park neighborhood, home to several small hotels, some with quite reasonable rates. Particularly inviting is the Numero Uno, a mainstream but gay-welcoming inn with a pretty courtyard and both standard rooms and efficiencies with kitchenettes - the restaurant, Pamela's, serves highly acclaimed West Indian cuisine. Somewhat more gay-oriented, L'Habitation guest house has large and simply but pleasantly furnished rooms and a lively little cocktail bar that's a nice place to while away the early evening. Foodies should check out Ocean Park's aromatic Kasalta Bakery, which serves delicious and creative breakfast and lunch fare, freshly baked pastries, and hefty sandwiches.

In the other direction, Old San Juan occupies a hilly promontory jutting into the Atlantic. This fabled historic district dates to 1521 and is famous for its weathered, pastel-hued colonial buildings, intricate iron work, narrow cobbled streets, and two massive historic ramparts. Here the romantic Hotel El Convento occupies a beautifully restored former Carmelite convent built during the 18th century. The 58 lavish guest rooms have handcrafted antiques, Andalusian tiles, marble bathrooms, and modern amenities like full stereo/VCR entertainment centers. Another characterful though more contemporary option is the Wyndham Old San Juan. This 200-room property has sumptuous rooms and is home to La Grita Lounge, which sometimes hosts gay-flavored events, typically on Thursdays.

Finally, there's the modern, some would say antiseptic, high-rise resort district of Isla Verde, where a posh Ritz-Carlton Hotel, Spa, and Casino opened in 2000. This lavish resort has top-notch facilities, including a state-of-the-art health and beauty spa. Trendy types prefer the nearby Water Club Hotel, an ultrachic boutique property on the beach with spare, avant-garde furnishings in its 84 rooms. The stellar restaurant, Liquid, serves memorable Nuevo Latino delectables like cinnamon-basted breast of chicken with garlic-potato mash and a coconut-peanut sauce. There's also a small pool and lounge up on the roof, and the staff is absolutely first-rate.

One key neighborhood that's less interesting as a place to stay but definitely deserves a visit is Santurce, which recently saw the transformation of an old hospital into the outstanding Museo de Arte de Puerto Rico. Here you'll find a rich permanent collection of local art and one of the best restaurants in Latin America, Pikayo, which serves artful renditions of nouvelle Caribbean fare in a softly lighted dining room overlooking the sculpture garden. Grilled shrimp with guanabana-fruit beurre blanc and chorizo is a show-stopping dinner entree.

Nearby Avenida Ponce de Leon cuts through Santurce's rather drab business district but at night blossoms into a vibrant nightclub strip. The traditional favorite in these parts is Eros, a bilevel club with a small but potent dance floor. Newer is swanky Maroma, a super trendy lounge catering to a stylish stand-and-model crowd. This place has a large central bar and several cozy nooks with ambient red and amber lighting. Both clubs draw a mix of lesbians, gay men, and heteros. Neighbors include Cups, a locals-oriented gay disco with great Latin music and minimal attitude, and De Incognito, a relatively new spot that opened in November 2001 and has campy drag shows and go-go dancers.

Wherever you go to play or to stay, try to set aside at least an afternoon and plan a couple of your dinners for Old San Juan. As you stroll its old-world lanes, be sure to take a look at San Juan Cathedral, an imposing structure that dates to 1549 and contains a marble tomb encasing the body of the island's first governor. Also be sure to walk out along the point to El Morro, a dramatic walled fortress from which Spanish soldiers defended the city from attacks by Sir Francis Drake. Within this massive compound you can explore a warren of hidden dungeons and tunnels (this may very well have been the inspiration for a few forbidding leather bars out there).

Old San Juan's rather new culinary hot spot is Calle Fortaleza, which has several acclaimed options - Tantra, an decadent space decked with iron and clay pots and serving exceptional upscale Indian fare, and the Parrot Club, which is especially famous in the gay community for its weekend brunch. The kitchen turns out stellar Latin fare like tamarind-glazed baby back ribs. A little more expensive, Trois Cent Onze is an elegant, tropical space where you might sample mahimahi fillet with black truffle oil, pureed pumpkin, and nutmeg. A few blocks away, Amadeus has been a gay fave for decades, serving burgers and salads as well as more elaborate Continental-meets-Caribbean fare like plantain gnocchi with an Italian sausage sauce.

Save time, and room in your stomach, for a stop at Mallorca, a quaint pastry cafe, that serves an eponymous sweet pastry that's absolutely addictive - these buttered and grilled delights are served with a sprinkling of powdered sugar. Charming Cafe Berlin draws its fair share of "family" for coffee, sweets, and light, healthful meals - it even gets a little cruisy in here on weekend afternoons.

If you have only the chance to spend one evening in Old San Juan, try to make it a Tuesday, and head for the Hotel El Convento, which is home to a pair of excellent restaurants. El Picoteo specializes in authentic Spanish tapas and has seating on a romantic tiled terrace overlooking the hotel courtyard. The second option, Cafe Bohemio, also serves great food but is perhaps best known in gay and lesbian circles for its Tuesday evening social mixer. Get your hair done, wear something sexy, and make a night of this festive event that draws just about everybody who's anybody in Puerto Rico's gay community. It's a spectacle you won't soon forget.