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Escape Plan Key West, Florida

by Kelsy Chauvin
Escape Plan Key West, Florida. Key West Sign (Photo by Pincasso)

Being in a Key West state of mind means sandals and shades, leisurely brunches on breezy porches, and, for every LGBTQ+ traveler, freedom to be your glorious self.

At the Key West International Airport we are greeted by a sign that reads: “Welcome to the Conch Republic.

It’s the first indication that you’re entering uncommon territory, a place where time slows down and where warmth is not just a temperature, it’s the vibe.

Here on this verdant isle of hibiscus and key limes, escaping daily routine is an irresistibly fun and friendly way of life. Being in a Key West state of mind means sandals and shades, leisurely brunches on breezy porches, and, for every LGBTQ+ traveler, freedom to be your glorious self. And the best part is that the island is small enough for you to enjoy its restaurants, bars, live shows, watersports, and famous sunsets without needing a car or WiFi. So unplug, grab that margarita, and let the island life flow.

Stunning Key West Sunset (Photo by Fotoluminate LLC)

EAT

Key West is synonymous with seafood, and you’ll find that and other temptations in abundance here. A delicious starting point is along a Key West Southernmost Food Tour (keywestfoodtours.com), which leads a walkabout to some of the best local restaurants. One of its favorite outposts is El Siboney (elsiboneyrestaurant.com), located outside of the main tourist area, and popular for patrons who want a taste of real Cuban home cooking and house-made sangria.

Key Lime Pie (Photo by Tatiana Goskova)

Key Lime Pie (Photo by Tatiana Goskova)

Brunch is a must at Blue Heaven (blueheavenkw.com), a mostly outdoor dining experience serving huge portions from its comfort-food menu, plus it has a fun bar with live nightly music. If you’re hankering for oysters by the marina, the Hall Shell Raw Bar (halfshellrawbar.com) has been shucking it live since 1972, and still serves some of the island’s best seafood from its big, eclectic harbor perch.

Duval Street is the main drag in Key West, and it’s lined with everything you need to have a great evening. For dinner, you can’t beat dining and people watching from the corner patio of Mangoes (mangoeskeywest.com), serving a top-notch conch chowder, Key West shrimp scampi, and jerk chicken, plus creative house cocktails. The balcony of Bagatelle (bagatellekeywest.com) is an upscale spot to take in Duval Street’s action while enjoying fresh local seafood, like the pan-seared black grouper and whole fried snapper. (Always reserve your table in advance, even for lunch, or risk a long wait.)

SLEEP

The island offers a bevy of great accommodations to choose from, but few are better located or as polished as The Marker Key West Harbor Resort (themarkerkeywest.com). Steps away from the marina, The Marker’s 96 luxurious rooms come with private balconies overlooking the harbor or the tropical courtyard swimming pool. Expect Key West’s easygoing version of a resort here, with mellow poolside drinks, dining, and afternoon live music, as well as bike rentals, pool games, and a hotel team eager to share the warm island spirit with guests.

Key West is famous for its smaller inns and B&Bs, many of them proudly welcoming queer guests. Alexander’s Guest House (alexanderskeywest.com) is one of the most beloved gay-owned hotels, and a favorite for many returning LGBTQ+ visitors. It’s an adorable, three-story “conch-style” historic house located a few blocks off Duval, with a shady courtyard and pool, homey living room, and daily continental breakfast and happy hour. (FYI, like many gay local inns, Alexander’s is adults-only.)

UNWIND

Chilling in Key West may mean watching nightly sunsets at Mallory Square, sipping perfect café con leches from Cuban Coffee Queen (cubancoffeequeen.com), or viewing the Florida Keys archipelago from the top of the Key West Lighthouse. Art and history lovers can dive deep into local culture at the Key West Art and Historical Society (kwahs.org), which runs the Lighthouse and operates the marvelous downtown Key West Museum of Art & History at the Custom House, as well as the Tennessee Williams Museum on Truman Avenue.

Key West Museum of Art History at the Custom House (Photo by Chuck Wagner)

Key West Museum of Art History at the Custom House (Photo by Chuck Wagner)

Travelers here have the choice of new things to do every day of the week, and the single-best way to access them is with the Key West Vacation Pass (keywestvacationpass.com). It’s an unbeatable VIP coupon booklet that grants access to 23 different activities and attractions around town for just $55 total. With it, you can enjoy “buy one adult ticket and get one free” watersports like parasailing and snorkeling; do a sunset booze cruise; take a trolley or Conch Train tour; get admission to the Hemingway House, Key West Aquarium, and the Butterfly & Nature Conservatory; or just enjoy drink discounts at local bars and music venues. Remember to reserve directly with each vendor.

DRINK

Oh, the places you’ll drink. Few destinations rival such local cocktail culture as Key West, where lively open-air and open-door bars seem to occupy every downtown corner. LGBTQ+ tipplers will enjoy easy bar hopping along and just off Duval, especially the three blocks between Truman Avenue and Angela Street. There you’ll find beloved hangouts like Bourbon Street Pub (bourbonstpub.com), 22&Co (facebook.com/22tutuandCo), and 801 Bourbon Bar (801.bar). You may find drag fun popping up at any of these hotspots, though you’re guaranteed to catch unforgettable drag at Aqua Key West (aquakeywest.com) and the famous La te Da Cabaret (lateda.com/cabaret), both with nightly shows.

In such a sociable destination, LGBTQ+ travelers will find warm welcomes just about anywhere in Key West. So drink in a little history at Pepe’s (pepeskeywest.com), one of the oldest joints in town circa 1909, where even President Truman enjoyed a drink or two. Another well-aged watering hole is the Green Parrot (greenparrot.com), with live music and weeknight happy hours.

DO

When you’re ready to soak up more action, use your Key West Vacation Pass or book directly with locally owned harbor companies like Sebago Watersports (keywestsebago.com) and Fury Water Adventures (furycat.com) for jet-ski rentals, kayaking trips, paddleboarding eco tours, sailing excursions, dolphin watching, and reef snorkeling.

Celebrating Pride In Key West (Photo courtesy of Fla-Keys)

Celebrating Pride In Key West (Photo courtesy of Fla-Keys)

Another must for every LGBTQ+ traveler is a visit to the Key West Business Guild (gaykeywestfl.com) at 808 Duval Street. It’s a small office with a huge array of intel about the best goings-on in town, including what’s on at different clubs and ahead for Key West’s big annual calendar of events, whether that’s Pride, Womenfest, Big Gay Key West, Tropical Heat, and more. This non-profit guild, which embodies the island’s longtime motto “One Human Family,” has been active since the 70s, actively promoting LGBTQ+ travel to Key West, and always working with local businesses to support the local queer community and embrace diverse travelers. In other words, the association is doing the kind of work that benefits all LGBTQ+ travelers and the proprietors who love them—and together they’re shoring up the kind of out-and-proud world we want and need.


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