People love to shop in Old San Juan because it offers the widest variety of unique shopping options in one pedestrian-friendly place. This is the place to go for fine jewelry, imported clothing and furnishings, cigars, folk art, tourist trinkets, and American chain stores, such as Marshalls, Walgreens, and Radio Shack.
For visitors seeking high-quality crafts by local artisans, Puerto Rican Arts and Crafts (204 Calle Fortaleza, 787/725-5596, daily 9:30 a.m.–6 p.m.) is your one-stop shopping spot. This large two-level store has everything from original paintings and prints to ceramics, sculpture, jewelry, and more.
For a small selection of authentic Caribbean crafts, stop by Tienda de Artesanías (Museo de Las Americas  in Ballajá Barracks, on Calle Norzagaray beside Quincentennial Plaza, 787/722-6057, Tues.–Fri. 10 a.m.–4 p.m., Sat.–Sun. 11 a.m.–5 p.m.). It has a nice but small mix of quality baskets, shawls, pottery, jewelry, Santos, art posters, and CDs.
Máscaras de Puerto Rico (La Calle, 105 Calle Fortaleza, 787/725-1306, Chilean [at] coqui [dot] net, http://home.coqui.net/chilean , Mon.–Sat. 10 a.m.–6:30 p.m., Sun. 10:30 a.m.–5:30 p.m.) is a funky, narrow shop in a covered alleyway selling quality contemporary crafts, including masks and small reproductions of vintage cartel posters.
There are two nearly identical shops on the same street called Haitian Gallery (367 Calle Fortaleza, 787/721-4362; and 206 Calle Fortaleza, 787/725-0986, haitiangallery [at] aol [dot] com, www.haitiangallerypr.com , daily 10 a.m.–6 p.m.). They both sell a great selection of Haitian folk art, including brightly colored primitive-style paintings and tons of woodwork, from sublime bowls to ornately sculpted furniture. There’s a small selection of Indonesian imports, such as leaf-covered picture frames and photo albums, and tourist trinkets.
Puerto Rico Homemade Crafts Gallery (403 Calle San Francisco, 787/724-3840, http://tallercocuyopr.com , Mon.–Sat. 10:30 a.m.–8 p.m., Sun. 10:30 a.m.–6 p.m.) is an excellent source for authentic local crafts and folk art—both traditional and contemporary. The shop carries a large selection of vejigante masks, plus native Taíno reproductions, cartel posters, coconut-shell tea sets, jewelry, and Santos.
The Poets Passage (203 Calle Cruz, 787/567-9275, daily 10 a.m.–6 p.m.) offers a funky collection of local arts, crafts, and books. The store is owned by local poet and publisher Lady Lee Andrews. Poetry nights are held every Tuesday at 7 p.m.
Tourist tchotchkes, shell jewelry, vejigante masks, gourds, beaded necklaces, and seed jewelry can be found at Ezense (353 Calle Fortaleza, 787/725-1782, ezense [at] yahoo [dot] com, daily 10 a.m.–7 p.m.).
Like Cuba, Puerto Rico  has a long history of hand-rolled cigar-making, and you can often find a street vendor rolling and selling his own in Plaza de Hostos ’s Mercado de Artesanías, a plaza near the cruise-ship piers at Calle Recinto Sur. There are also several good cigar shops selling anything you could want—except Cubans, of course. The biggest selection has to be at The Cigar House (255 Calle Fortaleza, 787/723-5223; 258 Calle Fortaleza, 787/725-9604; and 253 Calle San Justo, 787/725-0652; www.thecigarhousepr.com , daily 10 a.m.–6 p.m.). Trinidad, Monte Cristo, Padron 1926 and 1964, Cohiba, Perdomo, Macanudo, Partagas, Romeo and Julieta, and Puerto Rican cigars aged in rum are among those sold. They also sell tons of tourist trinkets.
For a more intimate setting, visit El Galpón (154 Calle del Cristo, 787/725-3945 or 888/842-5766, daily 10 a.m.–6 p.m.). This small selective shop sells a variety of quality cigars, Panama hats, masks, art prints, and superb vintage and contemporary Santos.
San Juan  has several Indonesian import shops. Eclectica (204 Calle O’Donnell, Plaza de Colón, and 205 Calle de la Cruz, 787/721-7236 or 787/725-3163, www.eclectikasanjuan.com , daily 10 a.m.–7 p.m.) has Indonesian imports specializing in home decor, purses, and jewelry.
Hecho a Mano (260 Calle San Francisco, 787/722-0203, and 250 Calle San José, 787/725-3992, fax 787/723-0880, hechom [at] coqui [dot] net) sells Indonesian decorative imports, locally designed women’s wear, funky purses, and jewelry. There’s another location at 1126 Avenida Ashford in Condado.
Kamel International Bazaar and Art Gallery (154–156 Calle de la Cristo, 787/722- 1455 or 787/977-7659, kamelimports [at] yahoo [dot] com, daily 10:30 a.m.–6 p.m.) sells inexpensive Indian clothing, jewelry, rugs, beaded handbags, and reproduction paintings on canvas.
Costazul (264 Calle San Francisco, 787/722-0991 or 787/724-8085, fax 787/725-1097, sferco [at] caribe [dot] net, Mon.–Sat. 9 a.m.–7 p.m.) sells a great selection of surf and skate wear for men and women, including Oakley sunglasses and clothes by Billabong and Quiksilver. During surf season, it also stocks boards and related gear.
There are dozens of high-end fine-jewelry stores in Old San Juan , especially along Calle Fortaleza, including N. Barquet Joyers (201 Calle Fortaleza, 787/721-3366 or 787/721-4051, fax 787/721-4051, nbarquet [at] spiderlink [dot] net, daily 10 a.m.–5 p.m.); Casa Diamante (252 Calle Fortaleza, 787/977-5555, daily 10 a.m.–6 p.m.); and Emerald Isles (105 Calle Fortaleza, 787/977-3769, Mon.–Sat. 11 a.m.–6 p.m.).
Vogue Bazaar (364 Calle San Francisco, 787/722-1100, Mon.–Wed. and Fri.–Sat. 10 a.m.–6:30 p.m. specializes in pre-Columbian reproductions, gemstones from South America, and purses from Thailand.
Thrift-store shoppers and collectors of vinyl will love Frank’s Thrift Store (363 Calle San Francisco, 787/722-0691, daily 10 a.m.–6 p.m.). Come here to peruse the enormous used-record collection, from ’80s kitsch to fresh electronica. There’s even a turntable available, so you can listen to the stock before you buy. But this cluttered labyrinth of rooms is also packed with the widest assortment of junk and collectibles you could ever imagine. Decorative items, old photographs, dishes, toys, clothes—you name it.
Spicy Caribbee (154 Calle de la Cristo, 888/725-7529, www.spicycaribbee.com , Mon.–Sat. 10 a.m.–7 p.m., Sun. 11 a.m.–5 p.m.) sells Caribbean sauces, spice mixes, coffees, soaps, fragrances, candles, cookbooks, and more.