If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiating out from the bay on the Atlantic Ocean that was discovered by Juan Ponce de León. More than a third of the island's nearly 4 million citizens proudly call themselves sanjuaneros. The city may be rooted in the past, but it has its eye on the future. Locals go about their business surrounded by colonial architecture and towering modern structures. By 1508 the explorer Juan Ponce de León had established a colony in an area now known as Caparra, southeast of present-day San Juan. He later moved the settlement north to a more hospitable peninsular location. In 1521, after he became the first colonial governor, Ponce de León switched the name of the island—which was then called San Juan Bautista in honor of St. John the Baptist—with that of the settlement of Puerto Rico ("rich port"). Defended by the imposing Castillo San Felipe del Morro (El Morro) and Castillo San Cristóbal, Puerto Rico's administrative and population center remained firmly in Spain's hands until 1898, when it came under U.S. control after the Spanish-American War. Centuries of Spanish rule left an indelible imprint on the city, particularly in the walled area now known as Old San Juan. The area is filled with cobblestone streets and brightly painted, colonial-era structures, and its fortifications have been designated a UNESCO World Heritage Site. Old San Juan is a monument to the past, but most of the rest of the city is planted firmly in the 21st century and draws migrants island-wide and from farther afield to jobs in its businesses and industries. The city captivates residents and visitors alike with its vibrant lifestyle as well as its balmy beaches, pulsing nightclubs, globe-spanning restaurants, and world-class museums. Once you set foot in this city, you may never want to leave.
In cosmopolitan San Juan, European, Asian, Middle Eastern, and chic fusion eateries vie for your attention with family-owned restaurants specializing in seafood or comida criolla (creole cooking, or local Puerto Rican food). U.S. chains such as McDonald's and Subway compete with chains like Pollo Tropical and El Mesón, which specialize in local cuisine. Many of the most innovative chefs here have restaurants in the city's large hotels, but don't be shy about venturing into stand-alone establishments—many concentrated in Condado and along Calles Fortaleza and San Sebastián, in Old San Juan. Old San Juan is also home to a number of notable new restaurants and cafés, offering more artisanal-style cuisine—crop-to-cup coffee, rustic homemade pizzas, and creative vegetarian food—at affordable prices. There's a radiant pride in what the local land can provide, and these enthusiastic young restaurateurs are redefining what Puerto Rican food is, bite by tasty bite.
Dress codes vary greatly, though a restaurant's price category is a good indicator of its formality. For less expensive places, anything but beachwear is fine. Ritzier spots will expect collared shirts and long pants for men (jacket and tie requirements are rare) and chic attire for women. When in doubt, do as the Puerto Ricans often do and dress up.
For breakfast outside of your hotel, cafés or local bakeries (called panaderías) are your best bet. It's rare for such establishments to close between breakfast and lunch; it's slightly more common for restaurants to close between lunch and dinner. Although some places don't accept reservations, it's always a good idea to make them for dinner whenever possible. This is especially true during the busy season from November through April and on weekends at any time of the year.
From Thursday through Sunday, it's as if there's a celebration going on nearly everywhere in San Juan. Be sure you dress to party, particularly on Friday and Saturday nights; Puerto Ricans have flair, and both men and women love getting dressed up to go out. Bars are usually casual, but if you have on jeans, sneakers, and a T-shirt, you may be refused entry at nightclubs and discos.
Well-dressed visitors and locals alike often mingle in the lobby bars of large hotels, many of which have bands in the evening. Some hotels also have clubs with shows and/or dancing; admission starts at $10. Casino rules have been relaxed, injecting life into what was once a conservative hotel gaming scene, but you still won't be allowed in if you're wearing a tank top or shorts. There are more games, as well as such gambling perks as free drinks and live music.
In Old San Juan, Calle San Sebastián is lined with bars and restaurants, although the hottest clubs are along and just off Calle Fortaleza. Salsa music blaring from jukeboxes in cut-rate pool halls competes with mellow Latin jazz in top-flight nightspots. The young and the beautiful often socialize in Plaza San José. Mid-January sees the Fiestas de la Calle San Sebastián, one of the Caribbean's best street parties.
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, Gant, Guess, and Ralph Lauren. 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 a not-to-be-missed neighborhood.
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 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.
San Juan is arguably one of the most important cultural centers of the Caribbean, both for its homegrown culture and the healthy influx of visiting artists that the local population supports. The city hosts the Puerto Rico Symphony Orchestra, the world-renowned Pablo Casals classical-music festival in winter, and an annual series of opera concerts. Many hit plays in New York and other large markets get produced locally, and there are often three or four other local theatrical productions taking place on any given weekend, many of them downright adventurous.
This legendary dive bar won't win any prizes for decor, but even still, it has an irresistibly artsy and welcoming vibe. Add your own message to the graffiti-covered walls (they have a B.Y.O.S, or Bring Your Own Sharpie policy), or hang your business card alongside the hundreds that cover the lighting fixtures. The jukebox has the best selection of oldies in town and locals crowd the back room for a game of pool. In the late afternoon, you might find owner David Jones, sitting at the bar who opened up the bar in the 1960s.