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El Castillo de San Felipe del Morro

More commonly known as El Morro, this stone garrison is the oldest freestanding fort in the Americas. Built between 1539 and 1797 by Spanish settlers on a rock-strewn promontory at the entrance of the San Juan Bay, it's a hulking pile of turrets, towers, walls, barracks, and dungeons that are wonderful to explore. A combination pass buys entry to both El Morro and Castillo San Cristóbal, another fort on the northeast edge of Old San Juan; it's larger than El Morro and usually less crowded.