24. Dunedin, FLGet More Info
Why go: Dunedin, one of the oldest towns on Florida’s Gulf Coast, is a great base from which you can explore the almost untouched white-sand beaches of Caladesi Island or Honeymoon Island. The subtropical temps hover around the mid-80s all summer, and you can always cool off at Florida’s oldest microbrewery, Dunedin Brewery.
Where to stay: The new Fenway Hotel pays homage to the jazz age—the building once housed the county’s first radio station, but now offers 83 rooms and suites, a rooftop bar overlooking St. Joseph Sound, a pool, and a lush front lawn complete with lawn games.
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