Aptly named one of Coastal Living’s “Happiest Seaside Towns in America” in 2015, this island town’s charming main street offers shopping and dining and meanders through stately 1920s homes leading straight to the Gulf of Mexico.

Once a fishing and farming community, this city in the heart of Sarasota County has blossomed into a vacation destination, where families play in the surf, hunt for prehistoric shark teeth, shop through downtown, bike around the Venetian Waterway Trail and "catch the big one" at the Venice Pier.