San Juan

Shopping in San Juan centers around Old San Juan and its boutiques selling fine art and folk art, clothing by international and local designers, and—for the tourists—all sorts of junky souvenirs and knickknacks. To avoid feeling overwhelmed by the latter, avoid shopping in Old San Juan on Mondays and Tuesdays, when the cruise ships dock and crowds swarm the narrow sidewalks. On the other hand, many smaller shops reduce their hours when ships are at sea, so call ahead or ask your hotel's concierge when you can expect most shops to be open.

Avenida Ashford in Condado is the Fifth Avenue of Puerto Rico, specifically the blocks just opposite La Concha hotel. Here, the usual designer gang—Gucci, Louis Vuitton, Cartier, Ferragamo—services the needs of glamorous locals who have moved into the neighborhood's luxurious condos. You'll also find local designers such as Nono Maldonado and all-around boutiques like Suola and Verovero. NB: The tattered sunglass shops and fast-food outlets make their unwelcome appearance just a few hundred feet down the street in either direction.

San Juan is jam-packed with galleries, many of them exhibiting art that goes well beyond the usual seaside pastels. The extremely popular Gallery Night brings a little bit of Soho to Old San Juan: More than 20 galleries and museums open their doors to visitors on the first Tuesday of each month (February through May and September through December) starting at 6 pm, though artistically inclined visitors give way to the more nightlife-focused as the evening wears on.