In Old San Juan, Calle Fortaleza and Calle San Francisco have everything from T-shirt emporiums to jewelry stores to shops that specialize in made-to-order Panama hats. Running perpendicular to those streets is Calle Cristo, lined with factory-outlet stores, including Coach, Dooney & Burke, Guess, and Tommy Hilfiger. On weekends, artisans sell their wares at stalls around Paseo de la Princesa.
With many stores selling luxury items and designer fashions, the shopping spirit in Condado is reminiscent of that in Miami. Avenida Ashford is considered the heart of San Juan's fashion district. High-end chain stores such as Louis Vuitton, Ferragamo, and Gucci are huddled together in what was formerly a derelict shopping strip. They are betting that the newly renovated luxury hotel La Concha will attract people ready to plunk down their platinum credit cards. A little farther west along Avenida Ashford are the one-of-a-kind clothing retailers that make this neighborhood worth a visit.
Just as in most other American cities, however, the real shopping occurs in the mall, and the upscale mall here, Plaza Las Américas—the largest in the Caribbean—is not to be missed. Known to locals simply as "Plaza," it's often host to artisan crafts fairs, art exhibitions, antiques shows, live Latin music, and pageants, depending on the time of year.
Thanks to Puerto Rico's vibrant art scene, numerous galleries and studios are opening, and many are doing so in Santurce, Puerta de Tierra, and other neighborhoods outside the Old City walls. If you prefer shopping in air-conditioned comfort, there are plenty of malls in and just outside San Juan.