1
Guys serious about partying might do well to check into Island House resort or get a day pass to one of Key West's last remaining clothing-optional accommodations, which has its own party scene. Otherwise, LGBTQ travelers have a wide choice of welcoming "adult-only" guest houses.
2
Get an early start (or a late finish from the night before) at the 24/7 Schooner Wharf Bar at the end of Williams Street where the first happy hour of the day begins at 7 am. Then drop by Harpoon Harry's, a blue-plate diner, which serves stomach-lining breakfasts 6:30 am - 3 pm a few blocks away on Caroline.
3
Spend the morning browsing shops around the harbor, maybe picking up some of Key West's famous hand-crafted sandals at Kino's or stopping at the Key West Cigar Club and Smoke Shop on Duval for a fresh-rolled or rare cigar as you time-travel back to when the island was known for its cigar factories.
4
Hit the beach. Smathers Beach, a two-mile-long stretch of sand out by the airport, is considered one of the best LGBTQ beaches in Florida. Its boardwalk invites skate-boarding, cycling and strolling with volleyball and ogling on the beach and fun in the water. Bring a picnic or buy lunch from a vendor or food truck.
5
Do the Duval Street Crawl, the trademarked name for Key West bar-hopping that includes drink specials, live music and crowds. Goes on all day in the open-air bars along Duval and nearby streets, but it's even better after dark. Start at Hog's Breath Saloon and move on down the street to some of the most popular pubs like Captain Tony's Saloon, Sloppy Joe's and Irish Kevin's, buying a souvenir T-shirt at each. Top LGBTQ destinations: 801 Bourbon Bar and Aqua for drag shows, Bourbon Street Pub for men only, the clothing-optional Garden of Eden on the upstairs deck of the Bull & Whistle. You'll need more than one night to do it right.
