Anna Maria Island, Florida
You won't find any Sunshine State kitsch on this off-the-radar barrier island just north of Sarasota, one of the last islands still offering a genuine Florida getaway. Chain stores are banned on Anna Maria Island, where beach cruisers and SUPs appear to outnumber cars and oceanfront porches spill onto sand as fine as baby powder. Pineapple Fish has the best selection of contemporary houses for rent here, with gulf front or canal side options – the latter is perfect if you're also going to rent a boat. Rent a kayak or paddleboard to explore the calm waters, where you're likely to spot dolphins and manatees. And join the nightly sunset ritual at the Sandbar, where you can wash down platters of peel-and-eat shrimp with frosty beers.