LGBTQ+ Travel Guide to Key West: Eat, Shop and Explore

Gay Travel Guide to Key West

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Key West, the Southernmost City, has arms wide open for the LGBTQ+ traveler. The city has a reputation for inclusivity, making it a go-to destination for the gay community. Whether it’s for relaxation, partying, or cultural exploration, Key West offers plenty of things to do, see, and experience for the queer traveler. Check out our LGBTQ+ travel guide to Key West to find the most welcoming places and experiences in the “Conch Republic.”

How to Get There: Planes, Trains, and Automobiles

There are lots of ways to get to Key West. The fastest and easiest is by air. However, if air travel isn’t your thing, check out your other options.

Planes: The nearest major airport is Key West International Airport which connects to most major cities. If it’s speed and convenience you’re looking for, flying is your best bet.

Trains: There is no train travel into Key West. The closest you can get is Fort Lauderdale. From there you can either rent a car and make the drive yourself, or jump on a bus.

Automobiles: Driving to Key West is part of your adventure, especially if you prefer “the scenic route.”  Driving down the Overseas Highway from Miami offers amazing ocean views as well as providing flexibility and the opportunity to make stops along the way.

Buses: Buses are a budget-friendly choice, and Greyhound operates routes into and out of Key West. The bus station in the city is on Caroline Street behind the Old Town Garage.

Ferries: If arriving by sea is more your style, there are ferry services to Key West from Fort Myers and Marco Island.

How LGBTQ+ Welcoming Is Key West

Key West is a playground for LGBTQ+ travelers, where the motto seems to be “come as you are.” The streets echo with a welcoming chorus, inviting everyone to join the fun. From cafes and bookstores to beaches and bars, the pride flag flies high, signaling a safe and celebratory space for all. In this corner of the world, it’s all about being yourself and making connections. You’ll find locals mixing effortlessly with visitors, sharing stories and making restaurant recommendations. Whether it’s over a cup of coffee or a sunset sail, the warmth and acceptance in Key West for the gay community is undeniable.

Key West Business Guild

As one of the oldest LGBTQ+ business organizations in the U.S., the Key West Business Guild is a non-profit organization dedicated to supporting and promoting LGBTQ+ businesses in Key West. They organize community events like Key West Pride and the Headdress Ball, contributing to the city’s reputation as an LGBTQ+ friendly destination. 

Gay Key West
Photo by Andriy Blokhin from AdobeStock

Key West Gay and Lesbian Community Center

Established with a mission to support and enhance the well-being of the LGBTQ+ community, the Key West Gay and Lesbian Community Center provides resources, education, and advocacy. It acts as a gathering place for the community, hosting events, support groups, and educational workshops, while also offering counseling services and health resources.

Queer Keys

Queer Keys is a non-profit organization dedicated to supporting the LGBTQ+ community in the Florida Keys. Their mission is to educate, empower, support, and celebrate the queer community. Queer Keys organizes community events, fundraisers, and educational programs, aiming to create a safe and inclusive environment for LGBTQ+ individuals. 

Gay Key West

Pride Events in Key West

Key West Pride – Key West Pride starts off with a bang, with a charity drag event. The five days that follow are packed with fun, and include a kick-off luncheon, nightly drag shows, quirky events like the “Tea on the Sea” sunset sail, “Vibrator races for Charity,” and a pool party where everyone’s invited. The week also includes a flag laser light show, the Big Gay 5K, and a dance party. It all wraps up with a parade honoring the diversity flag along with a memorable closing ceremony.

Key West Womenfest – Womenfest in Key West is a blast, offering a combination of beach fun, art, music, and parties. It kicks off with a welcome party with live music and an open bar. You can also enjoy the Ultimate Beach Bash and Cornhole Tournament, poetry readings, art exhibitions, sunset sails with live music, and even a burlesque show. There’s a clothing-optional sandbar trip, alt-rock concerts, dance parties, and a Key Lime Bike Tour. The weekend wraps up with a Sunday Drag Brunch and the classic Tea Dance​​.

Key West Tropical Heat – Tropical Heat in Key West is a whirlwind of fun activities. It starts with a kick-off party at Island House, followed by drag shows at Aqua and 801 Bourbon Bar, and male dancers at Bourbon Street Pub. The following days are jam-packed with excitement, including an all-male, clothing-optional day trip on the Blu Q, more drag shows, a “Heat Stroke” Fetish party, and a Skinny Dip Pool Party at Island House. But, it doesn’t stop there, the weekend continues with sunset sails, an exhibition party at Bourbon Street Pub, and wraps up with a Hot Naked Sunday Pool Party and Tea Dance at La Te Da.

Key West Bear Weekend – Key West Bear Weekend is all about fun in the sun and one-of-a-kind events. It starts with the Bear Soup Pool Party at Island House, a ‘Bearbie’ Pink Party at Bourbon St Pub, a key lime pie crawl around the island, and the raucous Beers & Bears into Cock Shock night. Shop at the Leather Master, enjoy more pool parties, and don’t miss the Masc 4 Masquerade Ball. The event wraps up with a Tea Party and a farewell party at Island House.

Key West Headdress Ball – A highlight of the Fantasy Fest celebration, the Key West Headdress Ball is hosted at the Coffee Butler Amphitheater. It’s a wild night of glitz and glamor as contestants strut their stuff on stage, each vying for the crown, and a cool $3,000, with each headdress more outrageous than the last. It’s like a fashion show, but the hats are the stars and the crazier, the better!

New Year’s Eve Red Shoe Drop – New York may have its Times Square ball drop to ring in the new year, but Key West has its own unique twist on that tradition with its Red Shoe Drop. A giant red high heel shoe with a fabulous drag queen perched inside, slowly descends as the clock ticks toward midnight. As the shoe makes its descent, the countdown begins. When it finally touches down, the night sky lights up with fireworks to celebrate the start of the new year. 

History Of Key West

In its early years, Key West was a significant trading post and naval base. The island’s strategic location made it a crucial player in international affairs, including during the Civil War, when it remained in Union hands despite Florida joining the Confederacy. The 19th century saw Key West thrive through industries like shipwreck salvaging, cigar manufacturing, and sponge fishing, becoming Florida’s wealthiest city per capita. The Overseas Railroad, completed in 1912, connected the island to the mainland, further boosting its economy. In the 1970s, Key West began attracting tourists, embracing its charm and laid-back lifestyle. This shift turned Key West into a tourist destination, celebrated for its diverse culture and community spirit.

LGBTQ+ Friendly Places To Stay In Key West

Whether you’re looking for a luxury hotel, full service, or budget-friendly, a cozy inn, a bed and breakfast, or a gay resort, Key West has the perfect fit for the LGBTQ+ traveler. Here are five of our favorites.

Alexander’s Guest House – Alexander’s Guest House combines the coziness of a B&B with the laid-back vibe of Key West, making it a favorite for LGBTQ+ visitors year after year. You can kick back and unwind in one of its comfortable rooms, relax poolside on a lazy afternoon, or enjoy the daily happy hour that’s perfect for socializing. Its convenient location makes it easy for guests to explore Key West, from its nightlife to its beaches.

Equator Resort Key West – Looking for where the boys are? Well, you’ve found them at the Equator Resort, a men-only spot with well-appointed rooms, pools to splash in, a jacuzzi to chill out in, and a daily happy hour where you can meet and make new friends. If you’re up for a good time with a side of social, Equator Resort is your kind of place.. 

The Island House – Island House is another men-only resort where there’s always something happening. Think pool parties, happy hours, and a crowd that’s all about having a good time. The rooms give you a cozy place to crash after a day of fun. It’s right in the middle of Key West, so you’re never far from the action. 

New Orleans House New Orleans House is where the party vibe of Bourbon Street meets the laid-back charm of the Keys. This men-only guest house sits right on Duval Street, putting you in the heart of all the action. With Key West’s nightlife steps away, and a rooftop terrace for those starry nights, it’s perfect for guys looking to mix relaxation with a bit of adventure.

Silver Palms Inn Like a sunny slice of paradise where everyone’s welcome, The Palms Hotel has this cool, easy vibe where you can kick off your flip-flops and just be yourself. Dive into their pool, laze under the palm trees, or strike up a conversation at the bar. The rooms are comfy, and you’re just a short walk from all the quirky fun of downtown Key West. 

Recommended Restaurants In Key West

A mishmash of flavors, where island life meets a food lover’s paradise, you find seafood is a big deal in Key West. Fresh catches turn up in everything from casual fish tacos to elegant gourmet meals. There’s a strong Cuban influence too, adding a spicy twist to the mix. You can find quaint cafes serving up hearty breakfasts and beachside joints dishing out cool drinks and sunset views. 

Tavern N Town – It’s where you go for a mix of good eats and good times. Tavern N Town’s got this cool vibe where you can watch the chefs work their magic in the open kitchen while you chill with a drink. From seafood to steak, they’ve got a bit of everything to keep your taste buds happy.

Jimmy Buffet’s Margaritaville – When you’re cruising down Duval Street, you can’t miss Jimmy Buffett’s Margaritaville. It’s like a mini-vacation with a side of cheeseburgers and frosty margaritas. The place buzzes with beachy tunes and is great for kicking back, island style. It’s a yummy slice of Key West life, right down to the last sip of your drink.

Smoked BBQ – If you’re craving some finger-lickin’ goodness, Smoked BBQ hits the spot. This “off-the-beaten-path” restaurant (it’s actually on a boat in a marina) is about smoky flavors and hearty portions. Think racks of ribs, pulled pork, and all the fixins you can dream of. It’s a casual spot where the food is the star and the napkins are plentiful.

Mangia Mangia – Mangia Mangia brings a homestyle Italian touch to Key West. It’s a cozy spot where pasta is the main event. They whip up everything fresh, from the spaghetti to the sauces. It’s the kind of place where you come hungry and leave feeling like part of the family, with a happy belly full of Italian goodness.

For more dining options, check out our Savoring LGBTQ+ Inclusivity: Key West’s Top Restaurants.

Things To Do & See In Key West

Key West is a place of sights and activities, where every day brings something new. You can dive into the crystal-clear waters for snorkeling or sailing, or stroll through streets lined with colorful historic houses. Whether you’re here for the beach life, the amazing sunsets, or the street scene, there’s always a corner of Key West waiting to be discovered.

Sunset Celebration – Sunset celebrations at Mallory Square are a must-see. As the sun goes down, the square comes alive with street performers, artists, and food vendors, all against the backdrop of a stunning sunset. It’s a daily party where the whole island gathers, and you’re invited!

Key Lime Bike Tour – For a different spin on sightseeing, the Key Lime Bike Tour is a blast. Hop on a bike and zip around the island, checking out hidden gems and famous spots, all while learning fun facts about Key West. It’s a great way to see the sights and work off some of that key lime pie.

Hemingway Home & Museum – The Hemingway Home and Museum is where history and feline fanciness meet. Home to the famous writer, every room whispers stories of the past. But it’s not just about Hemingway, it’s also the domain of the infamous six-toed cats. These furry residents strut around like they own the place, adding a dose of historical charm to your visit. 

After Hours Sunset Cruise – If you’re into something a little more relaxed, the After Hours Sunset Sail is your thing. Picture yourself gliding over the water as the sky changes colors, with a cool breeze and maybe a drink in your hand. It’s a peaceful way to end your day or start your evening.

For more water sport adventures, check out our Top Key West Water Adventures: Snorkeling, Diving, and More

Where To Shop & Stroll In Key West

Shopping and strolling go hand in hand in Key West, offering an experience filled with unique finds and beautiful views. The streets are lined with a mix of shops, ranging from boutiques to art galleries, where you can find everything from local crafts to high-end fashion. As you meander through the streets, the charm of the “Southernmost City” unfolds around every corner. 

Duval Street – Duval Street is the beating heart of Key West shopping, a long stretch where you can find just about anything. It’s a mix of art galleries, souvenir shops, and cool boutiques. As you wander, you’ll also stumble upon cafes and bars, perfect for a pit stop to soak in the local vibe.

Duval Street Key West
Photo by Xbrchz from AdobeStock

The Shops at Mallory Square – The shopping scene at Mallory Square is a treasure trove of local crafts and one-of-a-kind finds. The area hops especially as the sun starts to dip, with street performers adding to the  atmosphere. It’s a great place to pick up something special that screams Key West, from handcrafted jewelry to funky art pieces.

Sunset Waterfront Shoppes – Giving you shopping with a view, the Sunset Waterfront Shoppes is more relaxed, letting you enjoy the waterfront as you stroll, or browse through the stores. It’s ideal for finding that perfect vacation outfit, chic home decor piece, or that special something to take home for that special someone..

LGBTQ+ Bars, Clubs and Nightlife In Key West

The streets take on a new energy as the night owls come out to play, where locals and visitors share stories over drinks, or maybe dance the night away. If the bar scene isn’t your thing, you might just find an impromptu street performance that turns a walk down the street into a mini street festival. Whatever your pleasure, check out some of our favorite after hours spots.

Bourbon Street Pub – The Bourbon Street Pub is like a non-stop party. A place buzzing with energy, it’s where you can dance till your feet give out. There’s an awesome outdoor area, perfect for catching a breath of fresh air between dances. Whether you’re there to dance, catch a fun show, or just hang out with friends, it’s sure to impress.

801 Bourbon – The go-to for drag queen magic, 801 Bourbon knows how to put on a show that’s all glitz and glamor. The queens here are not just performers, they’re local celebs, and they know how to work a crowd. Pop in for a night of lip-syncs, laughs, and maybe a little sassy banter.

Key West Drag Queens
Photo by Rachel Covello

Aqua Key West – Aqua Key West is where the party’s at, with a splash of karaoke thrown in. It’s not just about watching; it’s about getting involved. Grab a mic, choose your tune, and belt it out. And let’s not forget their drag shows, they’re the kind that’ll have you clapping till your hands hurt.

La Te Da – Bringing a different flavor to the mix, La Te Da is chill but never boring. Here, you can enjoy some live music, or maybe a cabaret show if you’re lucky. It’s where you can have a drink, enjoy the tunes, and just soak up the Key West vibe. They also have some of the best food in town!

Annual Events and Festivals in Key West

Key West is alive with fun annual events, from its Film Festival to Fantasy Fest and everything in between, there’s always a reason for the community to come together to celebrate. Here are some of our favorites.

Fantasy Fest – Fantasy Fest in October is like the island’s own Mardi Gras. There are parades and themed parties that pop up left and right during this ten-day event. It’s about letting your imagination run wild and expressing yourself in the most outlandish, creative ways. Fantasy Fest is a no-holds-barred celebration of fun, freedom, and some good old-fashioned Key West quirkiness.

Key West Film Festival – A cinematic treasure hunt in November, where movie buffs and filmmakers share their love for the silver screen, the festival showcases a diverse mix of films. The event includes Q&A sessions, panels, and parties where film goers can rub elbows with actors and directors. 

Conch Republic Independence Celebration – It’s about reliving that time in April of ’82 when Key West jokingly said “bye-bye” to the USA. There’s a mock sea battle with tall ships firing water cannons and a conch shell blowing contest, where folks huff and puff to make the most music from a seashell! The streets come alive with a parade that’s as unique as Key West itself. 

Kelly McGillis Classic – The Kelly McGillis Classic in January is a sporting event with a twist of island fun. Named after the “Top Gun” actress and former Key West resident, this event brings together women’s flag football teams from all over the country for some friendly competition.

For more, check out our Five Biggest Festivals in Key West

Key West: Where All Are Part of One Human Family

“One Human Family” perfectly captures the island’s attitude of inclusivity and acceptance, resonating strongly with the LGBTQ+ community and its travelers. It started as a grassroots movement and quickly became the heartbeat of the island, symbolizing a commitment to welcoming everyone regardless of background, orientation, or identity. This message of unity is visible everywhere, from bumper stickers to local businesses, creating an atmosphere where everyone, especially LGBTQ+ travelers, feels part of a larger, accepting family.

**Disclaimer: There is a good chance that this post contains affiliate or sponsor links. If you make a purchase through them, we may receive a small commission at no extra cost to you (for which we are extremely grateful).

Also, while we do our best to highlight LGBTQ-friendly destinations and businesses, info provided is based solely on personal experience and recommendations by community partners. We hope that nobody experiences discrimination or homophobia while visiting Florida and beyond, but we make no guarantees. Please inform us if you experience discrimination or homophobia while visiting any destination so we can make updates to our recommendations.

Events are subject to change. Please check the events webpage for updates and schedules.

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