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