St. Augustine, Florida
17/21This town on Floridas northeastern coast bills itself as the first city in the nation, so theres much history to explore here. Plus, you can enjoy one of Floridas top gay beaches, at Guana Tolomato Matanzas National Estuarine Research Reserve. Wandering the citys downtown area, youll find more than 50 art galleries, a variety of accommodations, award-winning cuisine, and plenty of sunshine. Gay-friendly At Journeys End is a darling boutique inn, and House of Prism is a local queer advocacy group that hosts drag brunches and other events.