St. Augustine: America's Oldest City

St. Augustine was founded by Spanish explorer Pedro Menéndez de Avilés in 1565, making it the oldest continuously occupied European settlement in the continental United States — 55 years older than the Plymouth Colony, 42 years before Jamestown. The city passed between Spain, Britain, and the United States four times before Florida statehood in 1845, leaving behind a colonial urban grid and a masonry fort still standing on the Matanzas Bay waterfront. Castillo de San Marcos, built from coquina limestone between 1672 and 1695, is the oldest masonry fort in the continental United States and has never been taken by military force. Henry Flagler arrived in the 1880s with the Florida East Coast Railway money and built two hotels that became the anchor of Flagler College — the former Hotel Ponce de León, a National Historic Landmark of Spanish Renaissance Revival architecture.