St. Augustine: America's Oldest City
Pedro Menendez de Aviles landed on the Florida coast on August 28, 1565 - the feast day of St. Augustine of Hippo - and founded a settlement that has been continuously occupied ever since. St. Augustine is 42 years older than Jamestown, 55 years older than Plymouth Rock. The Spanish built the Castillo de San Marcos, the oldest masonry fort in the continental United States, to defend against English attack; the British eventually took the city anyway in 1763 but returned it to Spain twenty years later. The United States acquired Florida in 1821. Through it all, St. Augustine persisted - the oldest continuously occupied European-established settlement in the United States, though the indigenous Timucua who lived here first would note that 'oldest' depends on your perspective.
The Castillo
The Castillo de San Marcos was built between 1672 and 1695 of coquina - a locally quarried limestone made of compressed shells. The stone proved remarkably effective: British cannonballs sank into the soft coquina rather than shattering it. The fort never fell to military assault, though the city changed hands through diplomacy and treaty. The star-shaped fortification overlooks Matanzas Bay, its walls 12 feet thick, its design reflecting European military engineering adapted to Florida conditions. The Castillo is now a National Monument; visitors can walk the ramparts where Spanish soldiers watched for English sails. It's the oldest masonry fort in the continental United States, still standing after 350 years.
Flagler's City
Henry Flagler, Standard Oil partner turned Florida developer, transformed St. Augustine in the 1880s. He built the Ponce de Leon Hotel (now Flagler College), a Spanish Renaissance masterpiece designed by Carrere and Hastings. He built the Alcazar Hotel (now the Lightner Museum) and other structures. He extended his Florida East Coast Railway to St. Augustine and beyond, eventually reaching Key West. Flagler essentially created Florida tourism, and St. Augustine was his first project - an American Riviera for wealthy Northerners escaping winter. The buildings he commissioned remain the city's most impressive architecture, a Gilded Age fantasy of Spanish colonial grandeur that had little to do with actual Spanish St. Augustine.
Colonial Quarter
St. George Street runs through the colonial core - a pedestrian zone of shops, restaurants, and historical sites. The street is touristy but authentic in its bones: the buildings date from Spanish and British periods, the street layout follows colonial patterns. The Oldest Wooden Schoolhouse (claimed, not verified) dates to the 1700s. The Colonial Quarter living history museum recreates 16th through 18th century life. The Gonzalez-Alvarez House, occupied since the 1720s, bills itself as the 'Oldest House.' St. Augustine makes many 'oldest' claims, some verified, some disputed, all reflecting the city's foundational identity: we were here first.
Fort Matanzas
Fort Matanzas, 15 miles south of St. Augustine, guards the inlet where Spanish soldiers massacred French Huguenot settlers in 1565 - 'matanzas' means 'slaughters.' The small coquina tower, built in 1742, complemented the Castillo's defense by protecting the backdoor approach to St. Augustine. The National Monument includes the fort and the surrounding barrier island, accessible by free ferry. The massacre that gave the inlet its name established Spanish control of Florida; the French threat eliminated, Spain could develop its colony. It's a darker founding story than Plymouth Rock, but no less American.
America's Ancient City
Jacksonville International Airport (JAX) is 45 miles north; St. Augustine has no commercial service. The historic district is walkable; trolley tours provide orientation. The St. Augustine Lighthouse, dating to 1874 (replacing an earlier tower), offers climbing and harbor views. The Alligator Farm, operating since 1893, claims every crocodilian species. The beaches extend south to Anastasia State Park. From altitude, St. Augustine appears as a compact city on a peninsula between the Matanzas and San Sebastian rivers - the Castillo visible at the harbor mouth, the colonial street grid apparent, the old city distinct from modern sprawl - America's oldest city, 42 years before the English arrived.
From the Air
Located at 29.89°N, 81.31°W on the northeast Florida coast where the Matanzas and San Sebastian rivers meet. From altitude, St. Augustine appears as a coastal city on a peninsula - the distinctive star shape of the Castillo de San Marcos visible at the harbor mouth, the colonial core compact, the barrier islands stretching south. What appears from the air as a Florida coastal town is America's oldest city - founded 1565, 42 years before Jamestown, where Spanish coquina still guards the harbor.