There are plenty of reasons to make Key West a priority for your 2020 travel. From the welcoming LGBTQ community to the unique, tropical surroundings, it’s the perfect place for LGBTQ travelers to let it all hang out (sometimes literally).
Its proximity to Miami and other southern Florida (and Cuban) destinations make it a popular stop on extended trips. Whether you’re in Key West for a day, a long weekend or more, we’ve put together some simple one-day itineraries to help maximize your time. Mix and match or spread them out over the course of a few days, but here are some of our must-see sights.
For the Culture Vulture
The wacky, tacky t-shirt shops of Duval Street are hardly reflective of the breadth of history, arts and culture thriving in Key West. Island-based artists capture the gorgeous landscape in stunning paintings and photographs. Musicians, drag queens and cabaret performers pack out their theaters for evenings.
If you’re under a time crunch, there are a few stops that are must-sees. For example, no trip to Key West is complete without a tour around the historic Ernest Hemingway Home and Museum. Thirty-minute tours run all day, and the guides are knowledgable and dynamic. Take a short walk around the corner for a stop at the Tennessee Williams Exhibit. The legendary gay writer spent some of his happiest and most productive years in Key West, and this modest exhibition offers a really enriching, self-guided tour heavy on interesting artifacts from Williams’ life.
All that enrichment is sure to work up an appetite. Santiago’s Bodega sounds like the name of a great place to grab a bacon-egg-cheese sandwich and a lotto scratch-off, but don’t let the name fool you. The eclectic tapas spot is a favorite on the island. Inspired by Hemingway’s The Old Man and the Sea, the artistic flare extends to the lively atmosphere, hand-crafted decor and, of course, ingenious, contemporary cuisine with global flavors. It should be a crime to leave Santiago’s Bodega without an order of the Saganaki — a delicious dish with haloumi cheese at its center, served with brandy a la flambée.
Don’t stress about the calories or carbs. You can work off a bit of the meal with a short walk (a little over a half-mile) to the Harry S. Truman’s Little White House. A mercifully apolitical adventure, this important historical landmark offers a glimpse into Truman’s personal quirks, like a concealed poker table, while also honoring the parts of Key West Truman held so dear. Similar to the Hemingway House, the guided tour really enhances the experience.
From there, you’re not far from the Waterfront Playhouse. The intimate, 150-seat theater has hosted professional productions of Monty Python’s Spamalot, Twelve Angry Men, Equus, Urinetown and more. In March, you can catch Priscilla Queen of the Desert. Tickets are a fraction of Broadway’s prices, and the promise of exiting the theater into paradise (versus the throngs of Times Square) make it a much more pleasant experience.
For the Outdoor Adventurer
Talk to anyone in Key West (including the Mayor), and they’ll say you simply must get out on the water. There’s no better way for gay travelers to get on the water than with BluQ. The gay-owned and operated company has a men-only sail where swimsuits are optional. Snorkel among tropical fish and take a guided kayak tour through the mangroves. The entire excursion lasts about five hours, so it’s a significant chunk of your day. Beverages and lunch are provided, however, and the experience is well worth clearing your calendar.
Upon your return mid-afternoon, keep the aquatic adventure rolling with a stroll over to the Key West Aquarium. It’s the perfect place to learn more about the ecosystem you were just visiting with BluQ in a well-maintained space that’s easy to explore. Keep an eye out for regular opportunities to interact with and feed the wildlife.
A trip to the aquarium also puts you right in Mallory Square for sunset. Feel the breeze and watch the sun dip below the horizon alongside other travelers, locals and street performers.
Depending on your personal walking threshold, you can walk, ride-share or hop on the free Duval Loop Bus to the other side of the island for dinner. Louie’s Backyard serves up fine-dining with even finer views. The prime waterfront location, innovative cocktails and romantic atmosphere has garnered praise from Fodor’s, Frommer’s and more.
After dinner (and, let’s be honest, dessert, too), walk on over to the famed Southernmost Point. You won’t get the standard blue skies and bluer waters shot everyone else does, but you also will skip a lot of crowds queued up for their turn by the buoy. (Plus, your nighttime Instagram shot will look extra moody and romantic by comparison.)
For Those Up For Anything
Winding down is many vacationers’ primary objective. However, for some folks, the best way to relax is by turning up. Leave the suit and tie behind, and embrace the celebratory spirits of the island.
If you’ve only got one day to wring the most out of your trip to Key West, make it a Sunday. It may seem counterintuitive for weekend warriors used to raging Friday and Saturday nights. Don’t be mistaken: You can absolutely get lit any night in Key West, but, for a good sampling of the variety available, Sundays are best.
That’s partially due to Island House’s massive Sunday pool party drawing guests of the men-only, clothing-optional resort as well as locals. Even if you’re not staying at Island House, start the day with breakfast at the café. The food is great, and it gives you a perfect view of the pool to monitor when the party starts to pick up. The drinks flow freely, dangerously tasty shots are passed around and raffles keep spirits high. Trade your swimsuit for your birthday suit, and mix and mingle at one of the friendliest gay parties on Earth.
The Sunday tea dance at LaTeDa is also worthy of that superlative, but it makes a lot of sense, since the timing of the two events means the party moves en masse from Island House to LaTeDa where DJs spin a mix of ’70s, ’80s, ’90s and contemporary gay anthems for a multigenerational crowd on the dancefloor.
Make sure you’re not doing too much drinking on an empty stomach with a stop at Point5, the upstairs lounge of popular restaurant Nine One Five. (Local cabaret legend Randy Roberts had high praise for their walnut pistachio tacos served on romaine.)
Since you’re already on Duval Street, you have plenty of options to keep the party going after the sun has gone down. For drag, you can catch a show nightly at Aqua or 801 Bourbon Bar. If you’re looking for something a little randier, the go-go boys are on full display at Bourbon Street Pub, and the backyard boasts a (usually) men-only, clothing-option garden bar with pool and jacuzzi.
True night owls can bring on the dawn at Bobby’s Monkey Bar, a local institution and welcoming gay/straight mixed crowd makes this no-frills watering hole a good time for all. Karaoke is nightly and goes late, the bar closes at 4:30 a.m..