You aren't really going to spend your entire Key West vacation lounging around the guest houses and hotels, dining at the island's many affordable restaurants, and drinking its plentiful liquor, are you? It would be a crying shame to head all the way down to Florida's tip and not work your way in and out of its tropical, exotic nooks.
Looking to get high? Sign up for one of the island's many parasailing adventures. Fury Water Adventures has long been a gay-friendly go-to, but there are plenty of other options too: ParaWest Parasailing and Sebago Watersports, which also offers jet ski, kayaking, and sunset sailing excursions.
If you want to see the Keys from above but need a little more heft between you and gravity, take a seaplane tour over the sparkling blue and island greenery. The aptly named Key West Seaplanes can take care of your needs for about $189. But the truly adventurous, of course, will want to look into Skydiving into the Keys.
Naturally, many Key West-bound travelers want to get under the sea, and again there's no shortage of guides more than qualified to help you go down. Blu Q's is the premier gay sailing, snorkeling, and kayaking interest on the island, and Southpoint Divers or Subtropic Dive Center are great guides into the maze of awe-inspiring reefs and shipwrecks offshore. Floridays and No Worries tours also offer sailing adventures, a tranquil way to ride the high seas that often include champagne, sunsets, and unparalleled views of the island.
Speaking of the island, don't be too cool for the more touristy trolley tours. The Conch Train Tour and The Old Town Trolley can give you a general idea of the island's history as a welcoming refuge for outcasts, political exiles, and artists like Ernest Hemingway and Tennessee Williams, while the weekly Gay and Lesbian Trolley Tour takes a deeper look at the lavender-tinged pages of Key West's past. And be sure to check out the Audubon House and Garden, named after the famous naturalist who spent years drawing the Keys' wildlife, including many of the butterflies seen at the island's Butterfly and Nature Conservatory.
And while there's plenty you could and should do in Key West, we'll forgive you if you want to spend some of your playtime romping on the beach — something many of the island's guest houses lack. But to be honest, most Key West beaches suffer from poor sand or location (and are better in the upper Keys).
Gay travelers, however, are keen on Ft. Zachary Taylor near the Truman Annex at the island's southwest tip. There's plentiful beaches there, but also lots of other people, too. For a sandy strip a bit off the beaten path, check out Viking Beach in Bahia Honda Park 35 miles north of town or Boca Chica Key.
Or, if you're willing to pump those legs, just keep it simple by renting a bike and going for a ride. After all, isn't exploring what traveling is all about?