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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 Ferragamo and Gucci huddle together in a formerly derelict shopping strip, betting that the newly renovated luxury hotel La Concha will attract people ready to plunk down their platinum 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 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. For high-end shopping at stores like Saks and Louis Vuitton, head to the newer Mall of San Juan.
Thanks to Puerto Rico's vibrant arts scene, numerous galleries and studios are opening, and many are doing so in Santurce, Puerta de Tierra, and other neighborhoods outside the walls of Old San Juan.
At El Galpón, knowledgeable owners Betsy and Gustavo will fit you with a Panama hat ($65–$900), and you'll learn that the genuine article is actually made in Ecuador. They also carry a large selection of Puerto Rican santos, hand-carved wooden saints.
This shop carries Haitian masks, statues, paintings, and wooden works of art. The second floor houses a large selection of paintings from the Caribbean.
You might find a reproduction of your hotel at this shop, which specializes in tiny ceramic versions of San Juan doorways. The works are created by hand in the shop, which also carries fine art prints.
This is a good place to shop for high-quality folk art from around the island. You can also pick up local coffee and other food specialty items like hot sauce.
Aficionados of the famous Panama hat, made from delicately handwoven straw, should stop at Olé. The shop sells top-of-the-line toppers for as much as $1,000, as well as more affordable options that can be custom-fit. Take a few moments to browse the other goods for sale like decades-old santos and used books.
For one-of-a-kind santos, art, ceramics, and festival masks, head to Puerto Rican Arts & Crafts. All items are made by local artists.
