Sarasota, Florida

Vacations today can be spent soaking up the sights and beaches of sophisticated Sarasota, but this city took its time becoming the culturally rich place it is today. After marauding Spanish explorers expelled the Calusa people in the 15th century, this land lay virtually empty 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 protect their farms. Sailing boats and steamships were the only connection to the outside world until the Tampa railroad came in 1902. Sarasota then grew popular as a winter resort for the affluent, and the city’s arts institutions followed. Finally, circus magnate John Ringling decided to relocate his circus here, building 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.