Key West is a bona fide gaytopia! Nestled at the southernmost tip of the United States, just 90 miles from Cuba and surrounded by the shimmering waters of the Atlantic on one side and the Gulf of Mexico on the other, how can such a tranquil setting be anything but liberal?

Over the centuries, Key West and the Florida Keys have been the ports of pirates, famous sailors, and later, the home of inspirational writers like Ernest Hemingway. Nowadays, it's the perfect blend of Caribbean flair and American spirit, where a chilled-out ‘live and let live' approach to life dominates among its inhabitants. Not to mention, it has a flourishing gay scene away from pesky mainland politics.

This eclectic, delightful little island has loads to offer active travelers—kayaking, skydiving, shipwreck diving—and just the right amount of low-key activities in the form of beaches, shops, and galleries for those who just want to dip their toes into the Caribbean in a familiar LGBTQ+-friendly environment.

Table of Contents

1. General Tips
2. Transportation & Airport Transfer
3. Gay Hotels & Resorts in Key West
4. Sightseeing & Activities in Key West
5. Restaurants and Cafes
6. Key West Gay Bars and Clubs
7. Gay Beaches in Key West
8. Gay Events in Key West
9. Day Trips from Key West

General Tips

Getting around on foot or by bike are great ways to experience the island. During the day, you can head to Duval Street for shopping or check out the only gay and lesbian historic trolley tour. There’s also Higgs Beach, which has a poignant AIDS memorial. Gay life seems to spill into the mainstream on the island, and visitors can expect to feel welcomed and comfortable at any establishment, whether it's a bar, hotel, or shop. At night, there are plenty of options for fun, like 801 Bourbon Street for drag shows or Bourbon Street Pub for dancing.

Key West has a tropical climate, so you can visit nearly any time of the year and expect warm weather. The high season is typically from December to March, when visitors escape the winter at home to warm up on this beautiful paradise island.

You can download the Gay Key West guide for free. Just provide your email address and we’ll email you a PDF.

Transportation & Airport Transfer

If you’re flying into Key West, Uber or Lyft is the easiest and most cost-effective way to get to your hotel. If you’re coming from Miami or Fort Lauderdale, Greyhound Bus Lines, The Keys Shuttle, and Florida Keys Express Shuttle offer transport between Key West and Miami International Airport or Fort Lauderdale-Hollywood International Airport. You can also book an organized transfer from Miami or Fort Lauderdale.

In Key West, you can use convenient public transportation, taxis, rideshares, pedi-cabs, tour trains, the Duval Loop bus, trolleys, bicycles, or even your own two feet to see the sights. The Duval Loop buses go around the most important parts of the city and run every day, year-round. This free bus visits each stop every 30 minutes from 6 a.m. to 10 a.m., and every 15 minutes from 10 a.m. to midnight.

Gay Hotels & Resorts in Key West

Beachside Resort Keywest – The Key West Beachside Hotel is one of the highest-rated hotels in the Florida Keys, featuring a marina and water-sports rentals. This Marriott resort hotel is set on seven lush acres with a beach and waterfront pool for hotel guests. The property is gay-friendly and has long welcomed the LGBTQ+ community.

Silver Palms Inn – A gay-friendly, contemporary boutique hotel in the heart of Old Town. With its island-inspired charm and chic, contemporary spaces, the Silver Palms Inn is a green boutique hotel where you can relax as well as discover new adventures.

Parrot Key Resort – A gay-friendly hotel with glimmering pools, hammocks, and cocktails. Get a real taste of the tropics at The Grove Kitchen & Bar. Enjoy lush foliage right outside your room, with downtown Key West and the famous Smathers Beach just a quick shuttle ride away, and watersports available right onsite.

Island House Key West – An award-winning, clothing-optional resort for gay men and one of the first of its kind in the world. The property has a large poolside café and bar, and they regularly host social events onsite. The hotel offers a gym with a sauna, steam room, and multiple Jacuzzis.

Photo credit: Island House

Alexander’s Guest House – Beautiful grounds located in a quiet neighborhood, just a minute from Duval Street. Alexander’s Guest House is proudly gay-owned and operated.

New Orleans House – The only gay, all-male guesthouse on Duval Street, right in the heart of all the Old Town action.

Apartments - misterb&b

We’ve partnered with misterb&b to help curate the most LGBT+ friendly homestays. misterb&b is not a hotel or chain, but rather a booking platform for rooms, apartments and homes and it allows you to book from gay and gay-friendly hosts around the world. They have hosts in more than 200 countries and territories with more than 1 million total listings. Understanding the gay scene is much more easily done with the help of a local and home-sharing is one of the best ways to meet someone living in the city who knows how things work, where and when are the best nights to go out, and what places to eat at and which to avoid. misterb&b is our top choice if your priority is exploring the local gay scene.

Special Offer! Sign up with misterb&b and you will receive a free $10 credit to use on your first booking!

Sightseeing & Activities in Key West

Butterfly and Nature Conservatory – Take a stroll through a tropical paradise… walk through an exotic and inviting environment filled with hundreds of the most beautiful winged creatures in nature: butterflies.

Tropical Forest and Botanical Garden – Outdoor living museum with rental facilities for events, ceremonies, and parties. The only “frost-free” botanical garden in the continental United States.

Ernest Hemmingway House and Museum – Ernest Hemingway lived and wrote here for more than ten years. Calling Key West home, he found solace and great physical challenge in the turquoise waters surrounding this tiny island. Step back in time and visit the rooms and gardens that witnessed the most prolific period of this Nobel Prize winner’s writing career.

The Tennessee Williams Museum – This house-sized museum pays tribute to the legendary gay playwright. Williams lived in Key West from the 1940s to 1983, and the museum is filled with memorabilia of his work.

Key West Shipwreck Museum – Learn more about Key West's history of pirates and conquest through a literal treasure trove of historical artifacts.

BluQ – Voted the #1 all-gay watersports activity in Key West. Enjoy sailing, snorkeling, kayaking, and sunset adventures.

Harry S Truman Little White House – Florida’s only presidential museum, the Harry S. Truman Little White House has hosted presidents, prime ministers, and kings. As President of the United States, Truman spent 11 of his working vacations at the house.

Key West Food Tours – Discover the best of the local fare. Your guide is wildly passionate about the fresh, local, and historic cuisine found in Key West. They will be delighted to share their love of local food and culture with you. Book tour →

Old Town Trolley Tours – Discover all of Key West aboard the 90-minute fully narrated tour. Your ticket is good for two days to hop on and off at any of the convenient 12 stops to enjoy shopping, dining, and attractions all over Key West. Book tour →

Restaurants and Cafes

Smokin’ Tuna – Key West's premier music venue. Great local seafood and world-class musicians perform on a courtyard stage. Currently closed but moving to a new location soon!

LaTeDa – A beautiful hotel, restaurant, piano bar, outdoor bar, and cabaret. Tropical open-air fine dining in a casual atmosphere. Open seven days a week for breakfast, lunch, and dinner.

Old Town Tavern & Beer Garden – International tavern offering breakfast, lunch, happy hour, and dinner. Bar and restaurant open from 9 a.m. to 2 a.m. daily.

Hog’s Breath Saloon – Good times, great entertainment, and fun. Not to mention, the drinks and food are outstanding.

Schooner Wharf – This funky, open-air bar offers great musicians, fresh seafood, and unique special events.

Tempt Restaurant –Chef Andrew Nguyen curates an eclectic menu that changes weekly, offering dishes like Caribbean-spiced game hen, Mediterranean sea bass with Taylor Bay Scallops, and American Black Angus beef tenderloin with roasted bone marrow. Found within the Saint Hotel.

El Siboney – If you fancy a little Cuba away from Cuba, you can't do better than this traditionally Cuban-feeling restaurant. Plus, they have homemade sangria!

Blue Heaven – A kitschy café known for its whimsical ambiance and delectable brunch offerings, set in a lush garden surrounded by palm trees.

Boat House at Turtle Kralls – This popular, nautically themed seafood restaurant serves some of the freshest fish in town. Be sure to try the mahi-mahi sandwich!

Key West Gay Bars and Clubs

For such a small island, Key West has an incredible number of bars, clubs, and venues catering to the LGBTQ+ community, so there’s no shortage of places to drink and party. In fact, if you party too hard, you can even visit the Hangover Hospital the morning after for a 45-minute hangover treatment. There are no gay saunas or bathhouses in Key West, but many of the gay resorts are clothing-optional, and things are known to happen at night.

801 Bourbon – The legendary 801 has been a part of the Key West landscape for over 30 years. Enjoy the downstairs bar where locals enjoy people-watching, or head upstairs to the nightly cabaret that features the largest drag house on the island.

Bourbon Street Pub – A New Orleans-themed video bar featuring the Men of Bourbon Nightly. Live VJs, live shows, and multiple bars, plus a men-only, clothing-optional garden with a pool and jacuzzi.

Aqua Night Club – A popular bar and nightclub with drag shows nightly.

Grand Vin Wine Bar – Premier wine shop on Duval Street. Great porch sitting and people-watching, with excellent wines by the glass or bottle.

The Roost – An elegant and quaint bar specializing in craft cocktails, fine wines, and small bites.

D’vine Gallery – A unique, state-of-the-art wine-tasting bar at the luxurious Gardens Hotel. The self-serve wine dispensing system enables you to sample over 32 intriguing varieties.

1 Saloon – The only gay leather bar in Key West. It’s a historic local bar with late hours, drink specials, live entertainment, and an outdoor patio.

Gay Beaches in Key West

Higg’s Beach –This is the gay beach in Key West where you’ll find locals and visitors. You can lay out, snorkel, and admire the sunset from this quaint little beach. This is also where you'll find the Key West AIDS Memorial.

Smathers Beach – The largest public beach in Key West, located on the south side of the island.

Key West Pride – Held in June each year, the entire island comes together to celebrate. Events include free play readings, talent shows, pool parties, a street fair, and the pride parade, which takes place downtown.

Tropical Heat – A series of all-male theme parties, pool parties, and adult-oriented entertainment takes place each August. Attend individual events or buy a wristband for all-access to events during the long weekend.

Women Fest – This event welcomes women from across the globe to an annual celebration that has become one of the largest gatherings of lesbians and friends in North America. Each year, thousands of ladies come together over Labor Day weekend for a wide range of activities and events during four days of revelry and fun.

Day Trips from Key West

Fort Jefferson & Dry Tortugas National Park – Take a boat to Fort Jefferson in Dry Tortugas National Park, 70 miles across open water from Key West. During your voyage, enjoy the beautiful scenery of the Marquesa Islands and Boca Grande, and you may spot turtles and dolphins. Book tour →

Islamorada – A collection of islands that includes Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key, and Plantation Key, located midway between Miami and Key West (a 90-minute drive to either location), making it the perfect stopping point if you want to break up your drive. Book tour →

Image Credits / Featured Image: The Florida Keys & Key West

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