Established in 1521, San Juan is the second-oldest European-founded settlement in the Americas and the oldest under US jurisdiction. Shoehorned onto a tiny islet that guards the entrance to San Juan harbor, the old town was inaugurated almost a century before the Mayflower laid anchor in present-day Massachusetts, and is now a historic wonderland that juxtaposes historical authenticity with pulsating modern energy.

Beyond its timeworn 15ft-thick walls, San Juan is far more than a collection of well-polished colonial artifacts – it’s also a mosaic of ever-evolving neighborhoods such as Santurce, which has a raw vitality fueled by galleries, superb restaurants and a bar scene that takes over the streets at night.

And then there's the beaches. Silky ribbons of sand line San Juan's northern edge from swanky Condado to resort-filled Isla Verde. You can land at the airport and be out splashing in the azure waters an hour later.

Top reasons to go:

  • - TAKE A STROLL Wander the cobblestone streets of Old San Juan—the fortifications and governor’s mansion are UNESCO World Heritage Sites.
    - CLIMB A BATTLEMENT Explore Castillo San Felipe del Morro, the 16th-century fortress that dominates the waterfront; rangers provide a fascinating insight.
    - SHOP Head to Condado's Avenida Ashford, where you'll find most of the city's designer boutiques, including that of Nono Maldonado, one of the island's homegrown design talents.
    - CATCH SOME RAYS Balneario de Carolina, at the eastern tip of Isla Verde, is San Juan's best beach. Take time to parasail.
    - DINE ON THE STRIP Dine at Marmalade, just one of many stellar restaurants along the eastern end of Calle Fortaleza, a trendy strip that locals call "SoFo."

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