Florida's Most Historic Towns and Cities

Florida's history runs far deeper than theme parks and sun tourism. The state was contested by Spain, Britain, France, and Native nations for centuries before US statehood in 1845.

St. Augustine
Founded in 1565 by Pedro Menéndez de Avilés, St. Augustine is the oldest continuously occupied European settlement in the continental United States — 42 years older than Jamestown. The Castillo de San Marcos, a 17th-century Spanish fort built from coquina shell rock, is the oldest masonry fort in the continental US. The historic district's narrow streets, colonial architecture, and the Flagler College complex (built as a luxury hotel in 1888) make it one of the most architecturally rich small cities in America.

Pensacola
Founded in 1559 (even earlier than St. Augustine, though not continuously occupied), Pensacola has been under five different flags — Spain, France, Britain, the Confederacy, and the US. The Historic Pensacola Village preserves 18th and 19th-century buildings including the Lavalle House and the Museum of Commerce. The Naval Air Station Pensacola is the oldest naval air station in the US (1914) and home to the National Naval Aviation Museum.

Fernandina Beach (Amelia Island)
A port city that has flown eight flags — the most of any American city — including French, Spanish, Patriots of Florida, British, and Confederate. The Victorian-era downtown along Centre Street is one of the best-preserved in the South. The Palace Saloon, opened in 1903, claims to be Florida's oldest bar.

Tarpon Springs
The largest Greek community in the US, established when Greek immigrants arrived in the 1880s to harvest natural sea sponges. The sponge docks are still working; sponge diving demonstrations and Greek bakeries make this one of the most culturally distinctive small towns in Florida.

Apalachicola
A 19th-century cotton port that once handled a quarter of all US cotton exports. The well-preserved downtown has Federal and Greek Revival buildings from the 1830s–1850s. Today it's better known for oysters — Apalachicola Bay produces some of the finest in the world.