More bohemian, fanciful and literary than Miami, its neighbor to the North, Key West has been luring notable names—and gays, as in the case of Tennessee Williams—for over 100 years. According to local legend, it was here that Ernest Hemingway wrote A Farewell to Arms, and he definitely based To Have and Have Not on his experiences on the islands, and Tennessee Williams started A Streetcar Named Desire while whiling away his days on an island once-dominated by creative recluses, fortune seekers searching pirate ruins under the reefs, and military men stationed in the mid-20th Century.
Infused with Spanish, Jamaican, Caribbean, and European cultures (and known by the motto "One Human Family") Key West has gone through many phases over the years — from fairly unwelcoming backwater to depressed to self-confessed last resort, from party hot spot to family friendly destination — but consistently provides world weary travelers with an unabashed, unencumbered good time. Whether you're look for luxurious pampering at four-star resorts or a nonconformist escape at a quirky bed and breakfast, "The Conch Republic" can and will be anything you imagine.
1. The Marquesa Hotel: Consistently one of the highest ranked hotels in Key West, true elegance lies within The Marquesa Hotel's Victorian exterior. Whether in a standard room or a junior suite with covered porch, king-sized bed and sleeper sofa, everyone's treated like family, and their eponymous cafe, Cafe Marquesa, remains the top rated restaurant on the island and is open to non-guests, too. Even if you're not spending your stay here, try to swing for their seafood potstickers ($10) or porcini dusted scallops ($37). (Rooms range from $170-520/night. No children under 14 allowed.)
2. Hyatt Key West Resort and Spa: Located on the Gulf of Mexico side, this unassuming spot (pictured above) offers easy access to the crazy nightlife action while remaining sweetly serene, since tucked off Duval Street. It also has one of the best sunset views without the distraction of throngs of tourists. Book a jet ski tour of the island, take a quick fishing trip, or just enjoy an evening boat ride with a glass of wine, you can have that romantic experience or that much-needed R&R. You can't go wrong dining on the property at the SHOR Restaurant & Grill with Executive Chef Dan Elinan, who has combined a flair for Caribbean flavors with touches of Asian panache. We recommend the Seafood Hot Pot (with a coconut key lime broth), the Pecan Sweet Potato Crusted Yellowtail Snapper, or any of the Wagyu beef surf & turf options. A surprise was the lightness of the Fresh Catch ceviche, which includes cantaloupe and honeydew melons. And if you feel especially romantic, the property offers destination wedding options, with one of the best-appointed rooms for any festivity. (Rooms range according to season/availability.)
3. Southernmost Point Guest House: The truth is stretched a bit when it comes to pinpointing the nation's Southernmost Point. Officially, it's a privately owned island called Ballast Key (which, should you be in the market, is currently on sale for about $14 million), not this hotel nor is the nation's bottom even the nearby marker that declares "southernmost point." But let's not get bogged down by semantics. This is a vacation, and it will be one well spent if you pick this 19th Century Victorian mansion once owned by Cuban cigar-maker Eduardo H. Gato. Bright, high-ceilinged rooms, a central courtyard, charming verandas and lush palms give the Guest House an insular domesticity that will make the mainland seem like miles away. (Rooms during low season can be had for $100-140, while during high season they go for $140-200.)
4. Island House Key West: Boys looking to let it all hang out can do so at Island House, a gay resort with a well-reserved reputation for making the guest the center of attention. And you'll love it. In addition to a health club, dark, woody, masculine rooms, and a full restaurant the dinner menu includes Maryland crab cakes and lamb shank — Island House's isolated court yard is a 100% complete safe space for guys to be with other guys, which, sadly, remains a rarity in the real world. The woody, Caribbean-themed yet masculine rooms come in a wide-selection of shapes and sizes and have sound proof walls, light-blocking curtains, cable, plus three hours of free adult entertainment, and iPod docks should you decide to stay in, alone or with friends. (Rates vary. Economy rooms with shared bath can be booked for $99 during certain dates, while the one-bedroom apartments sometimes go for $450. Check their NSFW website for more details.)
5. Alexander's Guesthouse: Another gay resort, the mixed-gender Alexander's Guesthouse offers visitors a more contemporary, traditional stay than Island House. While still for adults-only — there are no persons under 21 allowed — Alexander's Guesthouse focuses more on the breakfast than the bed, though the beds are still quite plush. Rooms range in size and shape — from straight forward guest rooms to an apartment that sleeps four — but the mingling of modern touches, like flat screen televisions, and refined elegance, such as deep, dark woods and stark whites, run throughout. A full concierge service also makes planning days, meals and adventures completely worry free. (Guest rooms run at about $175 during peak season and $145 during off-peak; the apartment goes for $355 off-peak and up to $420 during peak seasons. Check Alexander's website for complete details.)
(Speaking of Key West, check out this video of outtakes from a shoot our friend Jason Rowan took at the Island House. Warning: probably NSFW)