Old San Juan's elegant El Convento (100 Cristo St., San Juan; 787-723-9020 or 800-468-2779; www.elconvento.com; from $205, suites from $490) is always popular with gay visitors. A magnificent, multi-story 17th-century convent transformed into a modern boutique hotel, the structure wraps around an open-air courtyard studded with enormous trees that were planted before the Yankee conquest.
Numero Uno Guesthouse (1 Santa Ana, Ocean Park, San Juan; 787-726-5010 or 866-726-5010; www.numero1guesthouse.com; from $80) is a charming, 13-room guesthouse that caters to a mixed gay/straight crowd. It's a nice choice for travelers seeking comfortable beachfront lodgings.
On Vieques' north shore, the Conde Nast-acclaimed, gay-owned and operated Bravo Beach Hotel (787-741-1128; www.bravobeachhotel.com; from $125) is a chic hotspot offering accommodations with private balconies. Rooms feature amenities such as iPod docks, Frette linens and handcrafted Ernesto Pena furniture.
The Parrot Club (363 Calle Fortaleza, San Juan; 787-725-7370; dinner entrees $18-36), a gay-friendly eatery serving authentic island cuisine with a contemporary flair, is increasingly popular with the gay and lesbian community.
Join trendy diners for dinner at the Water Club's Tangerine (Tartak Street #2, Isla Verde, San Juan; 787-728-3666; www.waterclubsanjuan.com; dinner entrees $21-29), for American-Asian fusion cuisine. Reservations are preferred.
Sit on the porch of Bananas (143 Flamboyán Street, Esperanza, Vieques; 787-741-8700; dinner entrees $15-17) with a fish sandwich, homemade potato chips and an ice-cold Presidente beer and watch the goings on of Main Street.
Eros is now called Krash Klub (1257 Ponce de Leon, Santurce; 787-722-1131; www.krashpr.com) and is still the main gay club in San Juan. Their weekly schedule features regular strippers and shows. It's open Wednesday through Sunday, and is busiest Fridays and Saturdays.
Nearby, Tia Maria's Liquor Store (Jose de Diego Avenue 22; 787-724-4011) is not actually a liquor store; it's a laidback gay bar and a good place to meet local guys for a drink or a game of pool before hitting the clubs.
CUPS (1708 Calle San Mateo, Santurce; 787/268-3570) is San Juan's women's bar.
The Caribbean National Forest, known as El Yunque (www.fs.fed.us/r8/caribbean/), is easily accessible from San Juan and offers 28,000 acres of trails through four types of forest, including the low-elevation, high-canopied rainforest.
While your image of San Juan may have been influenced by West Side Story's musical disparagement, the town of Old San Juan is as charming and impressive as any you might encounter in the Caribbean. Its structures date as far back as the 16th century, and many have been lovingly restored. The dramatic Fuerte San Felipe del Morro (Calle Norzagaray; 787-729-6960; www.nps.gov/saju), or El Morro as it is called locally, guards the entrance to San Juan Bay. Take a guided tour, or freely explore its dungeons, vaults, barracks and lookouts on your own.
If you do nothing else on Vieques you MUST check out the aqua-culture at Bio Bay -- named for its single-celled glowing bio-flagellates -- with Island Adventures (787-741-0720; www.biobay.com). When disturbed, these organisms give off an eerie glow. Watching a ray's luminescent shadow chase through the depths below or passing a hand through the little critters, you'll feel like you are in Fantasia.