STAY: Trendsetters like fashion designer Giorgio Armani overnight at the ultrachic Water Club (888-265-6699, www.waterclubsanjuan.com; rooms from $199). The minimalist boutique hotel goes aquatic down to the smallest details, including a soundtrack of breaking surf in guestroom corridors, water walls in the roofless elevators, and pillowy beds oriented for best sea views. The sleek restaurant Tangerine with a beachside terrace and rooftop bar, which parties deep into the night, makes the place a destination aside from check in. In town, stay at the atmospheric Hotel El Convento (800-468-2779, www.elconvento.com; from $275), a former convent with a lively central courtyard hosting several bars and restaurants.

DINE: Unlike elsewhere in the Caribbean, dining in San Juan is deliciously daring. Roberto Trevino, chef at the popular Parrot Club (787-725-7370), founded the Latin-Asian fusion spot Dragonfly (787-977-3886). The newest comer to their block on trendy Calle Fortaleza, AguaViva (787-722-0665) serves seafood in a cool oceanic setting. Tantra (787-977-8141), another Calle Fortaleza neighbor, does Indian-Latino fare. Elsewhere in Old San Juan, locals rave for the lively South American scene at Baru (787-977-7107).

SEE: Do walk the hilly, cobbled streets of Old San Juan and visit the El Morro ramparts. But for contemporary artworks and a five-acre sculpture garden, seek out the new Museo de Arte de Puerto Rico (787-977-6277) in the Santurce neighborhood.