The upper and middle Keys (Key Largo through Marathon) are known for many things, but nightlife is not one of them. The most nightlife you’ll find is in Key West, which has scores of great bars. Since you won’t have any trouble stumbling over those, we’re focusing on some unique nightlife opportunities.
Beautiful sunsets call for happy hour on a boat. Sunset sails are extremely popular and several companies offer them. We like Danger Charters in Key West. It offers a wind and wine cruise with a small group, so it is never crowded and always fun. However, there are many other operators of sunset sails up the Keys, so consider taking one wherever you are. It’s a beautiful and relaxing way to spend the early evening.
Despite having such a small community, Key West boasts three local theaters. Top-notch musicals, concerts and plays come to the Red Barn Theatre, Waterfront Playhouse and Tennessee Williams Theatre at Florida Keys Community College.
Finally, for another kind of show, hit one of the famous drag performances in Key West. The ones at 801 Bourbon Bar are always a good time. The ladies of 801 make sure the crowd is entertained with their raunchy humor, songs and more.