City Guide: Key West

There’s something about arriving at the southernmost tip of the country, or “Mile Zero” as Key West is called, that immediately forces your guard down and pops the protective bubble that you’ve become accustomed to with city living. Maybe it’s because the island’s official motto is, “One Human Family,” or maybe it’s because the ocean has you completely surrounded, but spend more than five minutes here and you’ll realize why so many people have dropped everything for a simpler life in Key West. Statistically speaking, only about a third of the island’s 28,000 year round residents are gay but those numbers don’t do justice to the unabashedly accepting culture of this place. There are rainbow flags everywhere you turn but they aren’t necessary. Unlike other cities in America where flags act as a mile marker or boundary indicating safe spaces, LGBTQ folks in Key West aren’t relegated to a specific neighborhood to walk arm in arm with a partner without risking a leering stare or worse. Everyone is welcomed here so relax those shoulders and let down that hair. This is the place to be yourself. You’re among family in Key West, and I don’t mean just the gay folks.

EAT: Fish and Key Lime Pie Go Together Like PB&J
There are seemingly endless places in Key West to get your brunch, lobster, and key lime on, so these are the places not to be missed:

The Flaming Buoy Filet Co: Tucked away from the droves of tourists on Duval Street, this little gem of a bungalow turned bistro is where fine dining meets local charm. Owners Scot and Fred have an eye for creating a romantic yet totally relaxed environment with welcoming staff, soft lighting, good wine and an adorable wrap-around porch. The lobster mac and cheese is an absolute requirement, but get it as an appetizer to make room for the filet mignon or catch of the day. This place is romantic but it’s not going to judge if you have to loosen your belt buckle from over ordering. (1100 Packer St, more info)

Martin’s: If you’re an eggs benedict fan, this is the place for Sunday brunch. They have over nine different kinds to choose from including lobster, crab cake, yellowtail, and even a wienerschnitzel benedict if you’re feeling creative. (917 Duval St, more info)

Kermit’s Key Lime Shoppe: You can’t visit the island that invented the key lime pie without stopping at the place that perfected it. You can get key lime pie practically anywhere in Key West but Kermit’s still takes the cake, so to speak. The store is full of samples to try before you buy including key lime taffy, peanuts, salsa, and marinades so don’t overdo it before you even try the pie. (200A Elizabeth St, more info)

El Siboney: Unless you’re Diana Nyad, Key West is the closest you can get to Cuba without a boat. Cuban food is plentiful here and the dishes at El Siboney are about as authentic as it gets. This unassuming restaurant is consistently voted “Key West’s Favorite Cuban Restaurant,” by its residents and you can tell from the bustling line at the take out window. With reasonable prices and massive portions, this place is worth a stop. (900 Catherine St, more info)

Orchid Bar: Before a night of partying, stop here first for a grown up drink. This tiny bar located inside of the Orchid Key Inn stocks top shelf liquor, infused elixirs, and fresh ingredients that make for a perfect cocktail. The staff here will mix you a concoction so yummy, you might rethink the rest of your evening plans. (1004 Duval St, more info)

The Porch: Cozy, casual, artsy, and hip are all words that locals would use to describe this bar. One word that never comes up in conversation though, is “pretentious.” Check out the impressive selection of craft beers on tap and 12 different wines by the glass. (429 Caroline St, more info)

Pearl’s Guest House: For ladies seeking ladies, stop by Pearl’s for breakfast or lunch and ask about upcoming events. From cocktail parties to pool parties, there is always something fun going on at Pearl’s. If you visit Key West during Womenfest in September, this place is the hub for lady parties. (525 United St, more info)

Aqua: This nightclub has a little something for everyone — drag, dancing, karaoke, and poker night. (711 Duval St, more info)

SLEEP: Guest Houses, Resorts, and Everything in Between
Sexy, upscale, or relaxed: all those lodging options are available in Key West.

Alexander’s Guest House: If you like the relaxed and social personality of a Bed and Breakfast, this LGBT guest house serves up the warmest welcome. With only 17 rooms and more amenities than a typical hotel (free WiFi, home cooked breakfast, free cocktails during Happy Hour,) you get a personalized experience without sacrificing style. Make new friends in the pool or canoodle in the jacuzzi with a partner. Be whoever you want here, as long as you’re comfortable. (1118 Fleming St, more info)

Island House: Boys! Boys! Boys! This male only, clothing optional resort boasts an attentive staff, ultra clean and tasteful facilities, and some pretty sexy amenities (health club complete with sauna and steam room, free drinks during Happy Hour, a 24 hour café, and complimentary “adult entertainment” channels in your room.) "Hot Naked Sundays" at the Island House is the hottest, all-male pool party in town. (1129 Fleming St, more info)

Casa Marina Resort: This oceanfront resort from the Waldorf Astoria collection offers a luxurious, though slightly less gay, alternative for travelers who prefer a more formal hotel experience. Unwind in one of two oversized pools (one of which is adult-only) or at the private beach in a hammock. For even deeper relaxation, book a spa package and truly indulge. (1500 Reynolds St, more info)

PLAY: Soak Up the Sun
Don't just lay by the pool: swim, dance, shop, and flirt.

Fury Water Adventures: Snorkel, parasail, jet ski, or do all of them in one day with Fury’s Ultimate Adventure package. (631 Greene St, more info)

Shop at Evolution: A boy can never have too many pairs of Andrew Christian underwear. Evolution has all of the name brands from Diesel to G-Star. (701 Duval St, more info)