San Juan Neighborhoods

Viejo San Juan, as it's known in Spanish, is the oldest colonial settlement in Puerto Rico, and actually is its own tiny little island. Three bridges unite this small land spit with the larger San Juan city. Surrounded by the Atlantic Ocean and San Juan Bay, it's dominated by a large bluff on the north end, and there you'll find "El Morro," the commanding old fort at the top of colonial Spanish battlements. Viejo San Juan's crooked winding streets are built in the old Spanish style—ladder like, so as you walk them you gradually climb the tall bluff, but without the strain of a direct ascent. That style also puts one side of the street in "sol" and another in "sombra," (sun and shade, respectively) no matter the time of day—another trick Spaniards devised to avoid the scorching heat. San Juaneros always walk in the "sombra." Atmospheric and enchanting, Viejo San Juan is the stuff postcards are made of—vivid blue, yellow, white and pink buildings, cobblestone streets, old porticoes and flower-covered trellises. It is made to wander through, with no particular destination in mind, as you soak up the history and architectural splendor. 

Tree-lined streets that invite walking, balmy beach breezes and a laid-back attitude have made Condado a prime neighborhood for visitors and residents for decades. Technically Condado is within the reaches of Santurce, but it's long had an identity of its own. Adjacent to Old San Juan, it's marked by De Diego Avenue to the east, and Wilson and Delcasse Streets to the West. Its main street—Ashford Avenue—leads into Old San Juan. Formerly an upper-class residential neighborhood (the Vanderbilts had a summer home here), it's now full of high-rise condos, hotels and nightclubs—although a few old-fashioned B&Bs and cafes remain. Home to a large gay community, many windows along its main streets are dappled with large rainbow flags.

Historically known as "Cangrejos," which is Spanish for crab (there once were a lot of the little critters here), this densely populated section of town has seen a lot of ups and downs. For a long time is was separate and apart from San Juan proper, but increasing growth meant it was swallowed up in the mid-1900s. A working-class barrio, it fell into decay in the 1970s and '80s, and only recently has begun to pull itself together, thanks in part to the Museo de Arte de Puerto Rico, which gave it new life. Galleries, cafes and clubs have started to appear, and it's a frequent destination for visitors staying at nearby Condado. It's not a place to stay out late in unless you are with locals or have arranged safe transportation back home, since you could easily wander down a wrong street.

Shop, eat, sleep, gamble and swim. This is life in Isla Verde, a wealthy enclave in San Juan known for mansions, nightclubs and casinos. It's west of Condado, north of downtown Santurce, and the farther east you go in Isla Verde, the closer you get to the island's main airport (keep that in mind when you pick a hotel, as you'll hear planes overhead). Isla Verde is the place to be seen on weekend nights for middle-class San Juaneros, who like to show off their nouveau riche status by having cocktails and dinner along flashy Isla Verde Avenue. It's quite posh, but ironically, also very close to San Juan's biggest public housing project. Consequently, there's a heavy police presence constantly patrolling the beaches and main streets—more as a crime deterrent than because there's a real problem. Beaches here are white and sandy, and many hotels have casinos too.