Gay Key West – Your Complete LGBTQ+ Travel Guide
One of the best things you can do when visiting Key West is to see Randy Roberts perform his cabaret show at La Te Da. Randy's dazzling show and hilarious comedic bits are wildly entertaining. The venue itself is gorgeous and perfectly located near the gay nightlife on lively Duval Street.
Overview – As one of the most laid back and accepting towns in America, Key West formally adopted "One Human Family" as its motto back in 2000. Recognizing that all people are created equal, the move sought to formalize its status as a safe, diverse, inclusive, and welcoming destination for all.
Although it's not as wild, bohemian, and inexpensive as in years past (Trai used to have annual family road trips here in the 90's and 00's!), Key West remains a must visit destination for the LGBTQ+ traveler.
History – Why is Key West so gay? Like many popular gay travel destinations—think Fire Island, Provincetown, or Zipolite—the remoteness of Key West attracted artists, writers, and other creatives as a place they could come to be themselves. Playwright Tennessee Williams and his buddy Leonard Bernstein were two of the first in the 1940s. Then, in 1967, one of the gay natives built the very first resort on the island at 1 Duval Street called Pier House. Throughout the 1970's, things really kicked off with more and more creatives from the Northeast coming to Key West to escape the cold. In the 1980's, people started coming down for a different reason with the AIDS crisis. As outcasts in their own communities, many came to Key West for its welcoming, come as you are vibe. From there, Key West just blossomed into the LGBTQ+ mecca that it is today. There is also so much incredible history to explore in Key West from the birthplace of Pan American World Airways to The Little White House used by American Presidents like Harry S. Truman, Dwight Eisenhower, John F. Kennedy, Jimmy Carter, and Bill Clinton.
Top 10 Things To Do in Key West
Hop on the Conch Train -For that classic overview of Old Town Key West, buy a ticket for this 75-minute sightseeing tour. A must for first time visitors.
Snap that required tourist photo -Join the line to take your picture in front of the southernmost point in the continental United States—just 90 miles from Cuba!
Visit Hemingway's House -Open everyday from 9am-5pm, explore the Ernest Hemingway Home & Museum. It's the most popular tourist attraction in Key West and also home to the first swimming pool on the island.
Hit the gay beach -Join the gays at Higgs Beach were you will also find the Key West Aids Memorial. We find this beach too rocky for us and prefer sunning by the pool at one of the many gay guesthouses.
Make a splash at a gay pool party -Meet other gay locals and visitors at Island House's weekly gay pool parties on Wednesdays and Sundays! Day passes are available.
Sail with gay-owned Blu Q -Swim naked on the all male day trip or join the LGBTQ+ sunset sail with BYO alcoholic beverages. We've done this trip many times, and it's alway spectacular!
Try the famous Conch Fritters -There are two things you have to try when you’re in Key West: one is Conch Fritters and the other is Key Lime Pie. See where to eat below for more deets.
Paddle a kayak through mangroves -Join a kayak tour through this unique coastal environment while spotting Florida wildlife in their natural habitat. Reserve through Viator. Dog-friendly too!
Watch sunset from Mallory Square -Head to the nightly sunset celebration at the most famous place in Key West to watch sunset. You'll find magicians, jugglers, clowns, psychics, local musicians, artists, and food vendors.
Go see Cabaret at La Te Da -As mentioned in our destination highlight above, don't miss Randy Roberts in his incredibly entertaining cabaret!
When to go - From mid-November to mid-April as snowbirds and travelers from colder climates flock to warm and sunny South Florida. In the summer and early fall (roughly June through November), it's the Atlantic hurricane season so definitely keep on top of any weather developments before traveling to South Florida during this time. In summer, popular gay events like Gay Pride, Bone Island Bare It All, and Tropical Heat bring many gay men to Key West. Around Halloween, Fantasy Fest, while not exclusively gay, is also a big draw as is New Year. For huge island events like these, book early—sometimes a year in advance—to find availability at the best places to stay.
Getting here – Located just 90 miles from Cuba, Key West is closer to the island nation than Miami. If you are ready for an epic roadtrip to the southernmost point in the continental U.S., rent a car in Fort Lauderdale or Miami and take the Overseas Highway (aka US 1) to its end point at mile marker zero in Key West. From Miami International Airport (airport code: MIA), the trip takes just under 4-hours to cover the approximate 159-miles. It's one of the best scenic drives in the country. We've also taken the one way bus from Miami to Key West as an add-on to a Miami gaycation.
Where to stay - In terms of the best gay hotels in Key West, we recommend either Alexander's Gay & Lesbian Guesthouse or men-only Island House. Thankfully, they are across the street from each other at the end of "Gay Guesthouse Row" on Fleming Street. Both are fabulous with luxury amenities and sell-out well in advance for popular island events.
We have enjoyed staying at or visiting Island House with a day pass many times. They are currently undergoing renovations which are modernizing the men-only, clothing optional resort. The sundeck and spa area are two of the most dramatic improvements as you can see from our photos. In terms of facilities, you can relax any time of day or night in the heated pool. We love pools and jacuzzis that are open 24-hours a day. The poolside cafe and bar also serve drinks, meals, and snacks 24-7. For accommodations, rooms need about a week of vacancy to renovate, so that is happening slowly over time. We previewed poolside Room 108 which is now bright, modern, and clean compared to the older rooms.
For our complete gay hotel review of Island House, check out our most recent Youtube video above!
For breakfast, our long-time 'go to' in Key West is Pepe's Cafe. You'll have to wait as it's a popular place, but it's worth it for the down home comfort food and friendly service. Across the street is the Cuban Coffee Queen's Waterfront location where you'll find excellent coffee to go and the vintage postcard Key West Mural.
Where to find gay nightlife – Most if not all of the gay nightlife is found on lively Duval Street. We recommend starting your night at the Cabaret at La Te Da (1125 Duval), and then moving to Bourbon St. Pub (724 Duval) for live music and/or male dancers or upstairs at 801 Bourbon Bar (801 Duval) for the nightly drag shows.
If you are looking for a gay bar during the day, we like the poolside bar at Bourbon St. Pub within the New Orleans House hotel and entertainment complex. The bar is located by the large pool and 15-man clothing optional jacuzzi. It's open until late and clearly the place to be day or night.
Where to find gay beachgoers – At the end of Duval Street on the opposite end as Pier House, you will find South Beach where famed gay playwright Tennessee Williams swam every morning. He said, “I work everywhere, but I work best here.” Although not the main gay beach today, it's clean, sandy, and has services like a cafe.
Where to find gay male massage – When you need a break from the sun, Island House offers poolside massages in a private cabana.
Where to find gay shops – Located at 721 Duval Street, we found Trai's iconic "EYW" Pan AM T-shirt (see dinner pic at Thirsty Mermaid above) at Graffitti, hands down the best gay men's boutique in Key West. During the Bone Island Bare It All gay event, you can even shop here in the nude!
Gay Key West Visitor Center – To learn more about gay Key West, stop at 808 Duval Street for one of the only gay visitor centers we have ever been to!
Wine/Liquor store – Conveniently located wine and liquor store at 705 Duval Street.
Travel Credit Card – For the best travel credit card, we recommend the Chase Sapphire Reserve. We use it to book free stays with reward points, trip cancellation and interruption insurance, primary car rental insurance, lounge access through Priority Pass, and to avoid foreign transaction fees just to name a few of this card's incredible perks. To learn more, click here. Even though there is a hefty $550 annual fee, you get a credit of $300 for travel (i.e. airfare, uber, etc). For the remaining $250, the card easily pays for itself with free food and drinks at the complimentary airport lounges we frequent. Also, if you don't have global entry yet, another card benefit covers that application fee! Trai has had the card since 2017, and it's his only credit card.
Travel Experiences – Discover authentic, unforgettable experiences and explore the world with Get Your Guide. They offer top-rated tours and activities in Key West. We have used Get Your Guide for numerous adventures around the world.
Shop Our Travel Essentials – To keep all of your electronics charged around the world, we recommend this universal international travel power adapter. It's also the one airline crew receive! For more of our favorite travel essentials, check out our Amazon Storefront.
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Hi! We're Two Gay Expats
Hola amigos and welcome to our gay travel blog! We are Andy and Trai, a gay couple traveling the world with PRIDE 🌈 …and our rescue dog, Pattie!
After meeting in San Francisco in 2018 and later moving to Chicago, we decided to quit our jobs in 2021, sell everything, and become Two Gay Expats!
If you’d like to follow our adventures, be sure to subscribe to our YouTube channel and add us on social media using the links below. We’d also love to hear from you and meet up if we’re in your city!
❤️ Andy + Trai