The southernmost city in the continental United States, nestled at the very end of the Florida Keys, closer to Cuba than Miami, and the capital of the imaginary Conch Republic, Key West is both wildly popular and truly eccentric. Your first clue will be the many laid back residents who like you, came for a visit at first, but afterwards quite literally never left. People stay for a good reason, as Key West, the most tropical of US cities, boasts extraordinary natural beauty and a nearly perfect and constantly sunny climate--you'll have to wait for the next ice age before the temperature dips below freezing here.
As a place where pleasure is a priority, Key West will never leave you bored. Special events like the Hemingway Days Festival and Fantasy Fest (recommended for adults only) can be a unique experience. Of course, you may want to join the locals for a drink or two at any of the dozens of bars that populate the island. One favorite is the waterfront Schooner Wharf Bar, where local bartenders like Island Skip tell their tells of love and adventure on the high seas of the Conch Republic.
Key West is a very gay friendly destination. Good starting points for information include the Key West Business Guild and the Key West Gay & Lesbian Community Center. Several gay friendly bars on Duval St. such as the Bourbon St. Pub and La Te Da are easily identifiable.
Dry Tortugas National Park
A day excursion to Dry Tortugas National Park, reachable via a high-speed, hour-long ferry ride, is an experience not to be missed. Not only is the trip itself enjoyable, but once there you can see the amazing Fort Jefferson. A truly massive brick fort built right in the middle of the Gulf of Mexico in the 19th century, it exudes history and is a great place for amateur photographers to score some prize-winning shots.