Old San Juan commands breathtaking views of the Atlantic as it celebrates over 500 years of well-preserved Western culture.  Standing on the bluffs of Old San Juan, it is easy to imagine the conquests that the island’s earliest explorers must have envisioned.

 

In his search for gold and the “Fountain of Youth,” Juan Ponce de León made claim to Borinquen—the island now known as Puerto Rico—and in 1508 founded the island’s original European settlement, Caparra. “La Ciudad Amurallada” (the walled city) of San Juan, just to the east of Caparra, was officially founded in 1521 and is today the oldest city under the U.S. flag.

 

In Old San Juan—one of the world’s most popular cruise destinations—more than 400 carefully restored 16th- and 17th-century Spanish colonial buildings line narrow streets cobbled with blue adoquine—furnace slag used as ballast on Spanish ships. Tidy houses painted in bright pastels are occupied by open-air cafes, art galleries, jazz clubs, shops and tiny museums that open a window onto the past.

 

Narrow lanes (best enjoyed on foot) give way to statue-studded plazas, handsome cathedrals and palaces and muscular fortresses. Among the latter, 74-acre Castillo San Felipe del Morro (“El Morro”) rises 140 feet above the sea, with 18-foot-thick walls and a maze of tunnels, dungeons, barracks, outposts and ramps. Castillo de San Cristóbal is one of the largest defenses ever built in the Americas, featuring five self-sufficient units connected by moats and tunnels.

 

Casa Blanca (White House), built in 1521, was the residence of Ponce de León’s descendants for over 250 years. Today it houses a museum of 16th-, 17th- and 18th-century history and a collection of Taino (native Indian) artifacts. The Catedral de San Juan, built and restored several times since the 1520's, contains the marble tomb of Juan Ponce de León and a relic of San Pio, a Roman martyr.

 

Old San Juan has the quaintness and exotic flavor of a Spanish village plus the ease and comforts of U.S. travel—no passports required—but there’s much more to see on this appealing island. Pristine white-sand beaches lead to forested landscapes and small townships, while contemporary San Juan has all the bustling activities of a major international city.