Pensacola, FL

Pensacola began as a Spanish settlement in 1559, six years before St. Augustine, but a hurricane forced its abandonment; Spain resettled the site in 1698. The Escambia County seat occupies the north side of protected Pensacola Bay, whose deep harbor made it the Gulf Coast’s busiest port during the Age of Sail. The 2020 census counted 54,312 residents. Naval Air Station Pensacola, commissioned in 1914 as the Navy’s first air station, underpins the city’s “Cradle of Naval Aviation” identity and hosts both the Blue Angels and the National Naval Aviation Museum. Seville Square’s annual Great Gulfcoast Arts Festival often draws more than 200 regional and international artists.