“It’s hard to imagine a more beautifully preserved and lovely walled colonial city” than Old San Juan, said Amy Engeler in Condé Nast Traveler. Just walk down its colorful 16th-century streets or gaze at the blue ocean against the marble tombstones of the Santa Maria Magdalena de Pazzis cemetery. Set at “the western end of a 2½-mile limestone islet, separated from the sprawl of the modern city,” the historic section of Puerto Rico’s capital seems remarkably intact. Yet for decades, economic and political enervation left it nearly empty and “crumbling in the sea air.” Only in recent years has the oldest settlement within the territory of the United States—and the second-oldest European settlement in the New World—been “restored to its original glory.”
Since being settled by Juan Ponce de León in 1508, this island outpost has suffered one upset after the next. English buccaneers pillaged it during the 1500s, and the Dutch burned it down in 1625, causing Spain to eventually construct the imposing fortresses that still enclose the oldest parts of the city. Today travelers can still climb upon and explore the interiors of the curving walls, some of which stand more than 100 feet high and “cast a shadow like an overgrown sand castle” over the entire coast. For almost four centuries, these walls protected San Juan from further devastation—until the Spanish-American War, when Puerto Rico came under U.S. protection.
When American troops stormed Old San Juan, it was “one of the most attractive cities in Latin America, with stately public buildings,” quaint cobblestone streets, and “wood-beamed, marble-tiled” homes from the 17th, 18th, and 19th centuries. Since being declared a UNESCO World Heritage Site, Old San Juan has gradually begun returning to that refined state. An abandoned hospital has been transformed into a fine-arts school. A 350-year-old convent has become the luxurious Hotel El Convento. A restaurant scene has revitalized Calle Fortaleza, where chef Robert Treviño cooks up Nuevo Latino cuisine at the Parrot Club and Aguaviva. The time to visit is surely now—before Old San Juan becomes the newest stop on every traveler’s itinerary.