Key West, Florida
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Much of the gay social activity in Key West takes place at resorts, some of which provide refreshments and snacks to guests during the afternoon and early evening. A handful of properties have bars open to the public, among them Pearl's Rainbow, the town's only guest house exclusively for women, and the ultra-cruisy, all-male Island House, which also has an excellent restaurant.

Most the town's gay bars are along Duval Street. Here, the La-Te-Da guest house has a poolside bar, an intimate piano bar, and the Treetop Cabaret Lounge upstairs. Down a few blocks, the New Orleans-inspired Bourbon Street Pub is a cheery place with a small bar up front with cocktail tables, a larger outdoor bar in back (along with a lively pool area and hot tub), and video screens galore. Many nights you can catch awful (but still entertaining) drag shows on the stage in back. The same owners run the lovably raffish 801 Bar, Key West's definitive neighborhood hangout since the 1970s. There's almost always a crowd of gossipy locals around the bar. The adjacent One Saloon caters mostly to leather-and-Levi's types and is reached through 801's back door. Aqua Nightclub is best known for its raucous drag shows, which are headlined by the in-house drag troupe, the Aquanettes. This lively place also has strippers some nights, an impressive dance floor with high-tech laser-and-sound shows, and a cozy video bar.

Key West has a number of inns that cater either exclusively or predominantly to the gay market. One of the best is Alexander's, a long-popular gay resort with the relatively unusual policy of being both clothing-optional and welcoming to both women and men. This makes Alexander's ideal for gay guys traveling with lesbian friends, or for any queer vacationers who enjoy a mixed-gender atmosphere. The effect is that the mood around the pool and hot tub tends to be less cruisy than at single-gender resorts. Aromatic tropical flowers, sundecks, rattan and wicker furnishings, and sparkling tiled bathrooms impart Alexander's with a classy but casual look. Also welcoming of both women and men but drawing a predominantly male crowd, Big Ruby's is less than a block from Duval Street, hidden behind high walls from noise and street traffic. The grounds feature towering palm trees and fragrant flowers, and an abundance of sundecks. Rooms are warm, contemporary, spotless, and full of light - all have TV/VCRs, mini-refrigerators, A/C, and ceiling fans. A complimentary full breakfast is included. As for the staff, you won't find a more professional bunch of guys in Key West.

Most of the town's men's resorts are along Fleming Street, the Historic District's main drag. Here you'll find Equator, which has plush rooms with contemporary Caribbean-influenced furniture. Designer fabrics, feather pillows with comforters, Mediterranean-tile floors, large closets, and excellent sound insulation add to the comfort of each unit. The tradeoff is that the Equator's grounds, although nicely landscaped, are smaller than at some of its competitors; there's a compact pool and an oversize Jacuzzi tub.
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