Entire vacations can be spent soaking up the sights and pretty beaches of sophisticated Sarasota, but this city took its time to become the culturally rich place it is today. Even after marauding Spanish explorers expelled the native Calusa people from this coastline in the 15th century, the land lay virtually empty. That is until the Seminole Wars inspired the Armed Occupation Act (1842), which deeded 160 acres and six months’ provisions to anyone who would settle here and bear arms to protect their farms. Sailing boats and steamships were the only connection to the outside world, until the Tampa railroad came town in 1902. Only then, as Sarasota grew popular as a winter resort among affluent Northerners, were the city’s first arts institutions established. One of those early tourists was circus magnate John Ringling, who decided to relocate his circus here, building himself a winter residence, art museum and college, and setting the struggling town on course to become the welcoming, well-to-do bastion of the arts it is today.
As the 1920s roared on, Ringling scooped up more property across the causeway in St Armands Circle and development crept up the dazzling barrier island beaches from south to north: lively, low-rise Siesta Key through upscale Longboat Key to slow, sweet, family-friendly Anna Maria Island.