St. Augustine lays claim to being the oldest city in the United States. Just 30 minutes south of Jacksonville in NortheastFlorida, St. Augustine is full of romantic ambiance and old world charm. It is best known for its remarkable historic streets and attractions, Spanish-style architecture, and panoramic bayfront views.
The walkable downtown is made up of narrow colonial streets lined with interesting locally-owned shops and outstanding restaurants. A trio of grand hotel buildings built in the late 19th century by railroad magnate Henry Flagler tower over the smaller, reconstructed historic houses, but the tallest building in town is just seven stories. One of Flagler’s former hotels is now home to a small, private liberal arts college whose students add a sense of pulsating life to the centuries-old town.
In St. Augustine you can dine on terraces overlooking narrow brick streets, view excellent art at unique galleries, and visit historic sites older than the United States itself. But the town is more than history and high culture. Feel like going parasailing over unspoiled beachfront or listening to famous bands play under the stars? St. Augustine has that too.
42 years before the English established Jamestown, and a full 55 before the Pilgrims landed at Plymouth Rock, the Spanish colonial empire settled St. Augustine. Founded by Pedro Menéndez de Aviles in 1565 as the colony’s capital and in an effort to protect Spain’s claims in Florida from the French at Fort Caroline (present-day Jacksonville), the town had a rocky start. Pirates attacked, as did the local Native Americans, and British privateer Sir Francis Drake burned St. Augustine to the ground in 1586. In response, the Queen of Spain dispersed funds to construct a masonry fort to protect the town, and construction on the Castillo de San Marcos began in 1672. The fort was never captured, despite multiple attempts, including a 58-day seige by British forces in which the town was burned again.
With the end of the Seven Years’ War and the 1763 Treaty of Paris, Florida moved from Spanish to British colonial rule. During the American Revolution, St. Augustine remained a haven for those loyal to the British Crown. A group of immigrants that fled from a colony in New Smyrna arrived in town in 1777 and made up much of the city’s population at this time, they were and are still known today as “Menorcans“. The second Treaty of Paris, which ended the Revolution in 1783, freed the original 13 colonies but gave Florida back to Spain.
The second Spanish period was characterized by neglect from the crown, as Spain was engaged in a war with Napoleon and France and regarded the colony of Florida as an unprofitable backwater. The United States, however, viewed it as key to its interests and sought to annex Florida, and they succeeded in 1819. The colony became a territory of the U.S. and St. Augustine continued to serve as its capital until 1824.
Railroad tycoon Henry Flagler first visited St. Augustine in 1883. Seeing potential, he returned in 1887 with a new company, the Florida East Coast Railway. Over the next decade, he constructed a railroad line down the Atlantic Coast of Florida, all the way to Key West. Three large Flagler hotels were built along the line in the city: the Hotel Alcazar, the Casa Monica Hotel, and the flagship Ponce de Leon Hotel. These three buildings began the Moorish Revival architectural style that today characterizes the town. Flagler also built a pair of churches and sparked the development that grew modern St. Augustine.