This city has it all: historic grandeur, hip nightlife, hot restaurants, great beach resorts, and an airport where the Customs officials don’t ask for American citizens’ passports. A Spanish stronghold from the 1500s until the end of the 19th century, its sights include El Castillo San Felipe del Morro aka El Morro, a World Heritage Site (c. 1540) and El Castillo de San Cristobal, the largest fortress Spain built in the New World. El Palacio de Santa Catalina aka La Fortaleza, built in the 1530s, is the oldest executive mansion in the Western Hemisphere, and El Catedral de San Juan Bautista contains the remains of Ponce de Leon who did not find that fountain of youth before his deadline.
History lovers and the partying crowd (admittedly, an odd mix) can stay right in Old San Juan at boutique hotels in colonial buildings, such as the Pop Art Hotel and Hotel El Convento. But here’s another option: lining the north shore of the city, including the Condado neighborhood, is an expanse of beach that’s home to the Caribe Hilton, the Conrad Condado Plaza, the San Juan Marriott Resort and Stellaris Casino and other hotels that offer a beach vacation that’s just a 10-minute drive from downtown’s restaurants, shops, clubs and culture.
The resorts offer exceptional dining, clubs, and casinos, but head back to Old San Juan to eat at Dragonfly or Marmalade, which offer fine fusion cuisine amid a hip vibe. The tapas at Rosa de Triana serve as a reminder that this neck of the woods was settled by Andalusians from Spain. San Juan has enough nightclubs to fill a phone book, but the most convenient one, aside from the one in your hotel, may be The Latin Roots in Old San Juan, because you can have dinner there, too, and not just any dinner, but melt-in-your-mouth roast suckling pig.
San Juan is the gateway for other resort areas, too, including Porto del Sol, Culebra and Vieques islands (there’s now a W on Vieques!). And just an hour to the southeast is El Yunque Rainforest, which any parrot could tell you is one of the great primeval parks of the Caribbean.
BEST TIME TO GO: December through May
FUN FACT: The oldest church still in use in the Americas is La Iglesia de San Jose (1522) in San Juan
GETTING THERE: Delta flies from Atlanta, Detroit, Minneapolis and New York (JFK) to San Juan
ENTRY DOCUMENTS: Government ID for U.S. visitors; valid passport for Canadians
CURRENCY: U.S. dollar
MUST-TRY LOCAL FOOD: Lechon, or roast suckling pig, at Kasalta or almost anywhere else in San Juan
BEST BUYS: Guayaberas, the comfortable, untucked, short-sleeve shirts sold in many shops