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Few American cities carry their age as openly as Saint Augustine. Founded by Spanish colonists in 1565, it holds the distinction of being the oldest continuously occupied European settlement in the continental United States, a fact that shapes everything from the street plan to the skyline. The old town sits on a narrow peninsula between the Matanzas River and the San Sebastian River, and its compact geography means that centuries of history are genuinely walkable, layered into a few dozen blocks of coquina stone, wrought iron, and terracotta.

The Spanish colonial quarter around the Cathedral Basilica of St. Augustine and the Plaza de la Constitución is where most visitors find their footing. The Castillo de San Marcos, the 17th-century masonry fort that guards the waterfront, is one of the most intact examples of Spanish military architecture in North America, and its sheer physical presence, rising from the shoreline in pale coquina blocks, does more to communicate the city's age than any museum exhibit could. Flagler College, housed in the former Ponce de León Hotel built by Henry Flagler in 1888, anchors the southern end of the historic district with its Spanish Renaissance towers and is a reminder that Saint Augustine attracted a second wave of reinvention during the Gilded Age, when Florida's east coast was being opened up by the railways.