Popular Events in Key West

For 25 years on New Year’s Eve, in front of the Bourbon St. Pub/New Orleans House complex, renowned Drag Queen, Sushi, “dropped” in a giant red high-heeled shoe. The legendary…

Relaxed and tropical, Key West Pride is part-vacation, part-celebration, all amazing. And since you’ll be in Florida, don’t say gay … SHOUT IT!

The event to go to when you want nothing between you and the sun. Bring sunscreen, you’ll need it everywhere. Yes, everywhere. This event happens twice a year; just in…

Key West ups the ante with four days of “all-male themed parties and adult-oriented entertainment.” Grab your guesthouse now.

Slow it down and heat it up at this four-day lesbian affair. From the beach activities to clothing-optional pool parties, you certainly won’t be bored.

You may not think Halloween when you think Key West. But grab your wigs, costumes, and face paint—you just might find yourself back every year.

Just some bears and cubs getting down in this tiny island town. And who know, bears may find more than a few reasons to let some sand in their fur.