Two Gay Expats - Key West, FL - Mile Marker Zero - Trai & Andy

Gay Key West – Your Complete LGBTQ+ Travel Guide

Written by Traivor Morrison
Published on
Known as one of the top international gay travel destinations in the country if not the world, Key West attracts over 250,000 LGBTQ+ visitors annually. With dozens of gay venues from clothing optional guesthouses to super fun bars and clubs, read on to see if visiting this island paradise is right for you!

DESTINATION HIGHLIGHT


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.

Two Gay Expats - Key West, FL - Motto - One Human Family
One Human Family

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.

Quotation Mark
Spanish settlers originally called Key West "Cayo Hueso," which translates to bone island, referring to the bones of the Indians who once lived in the Florida Keys. English speakers thought Cayo Hueso sounded like Key West and the name stuck.


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.

Two Gay Expats - Key West, FL - Pan Am Airways - First Office
Original Pan-Am Office
Two Gay Expats - Key West, FL - South Beach Key West
South Beach, the favorite of Tennessee Williams
Two Gay Expats - Key West, FL - The Little White House
The Little White House
Two Gay Expats - Key West, FL - Pier House Resort
Pier House Resort & Spa
Two Gay Expats - Key West, FL - Island House - History
History of Island House
Two Gay Expats - Key West, FL - Higgs Gay Beach - Aids Memorial
Key West Aids Memorial

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.

Two Gay Expats - Key West, FL - Conch Tour Train
Conch Tour Train
Two Gay Expats - Key West, FL - Southernmost Point Line
Line for Southernmost Point
Two Gay Expats - Key West, FL - Hemingway House - Entrance
Hemingway's House
Two Gay Expats - Key West, FL - Higgs Gay Beach - Pier
Higgs Gay Beach
Two Gay Expats - Key West, FL - Island House - Cafe - Happy Andy
Island House Pool Party
Two Gay Expats - Key West, FL - Blue Q Gay Cruises
Blu Q Gay Catamaran
Two Gay Expats - Key West, FL - Conch Fritters - Mallory Square
Key West Conch Fritters
Two Gay Expats - Key West, FL - Mallory Square - Sunset
Sunset from Mallory Square
Two Gay Expats - Key West, FL - Sunset
Key West Sunset
Two Gay Expats - Key West, FL - Gay Friendly Hotel Restaurant/Bar/Cabaret - La Te Da - Randy Roberts - Cher Impersonation
Randy Roberts Cabaret

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.

Two Gay Expats - Key West, FL - Southernmost Point
Southernmost Point in the Continental U.S.

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.

For those short on time, Key West International Airport (airport code: EYW) is served by Allegiant, American, Delta, JetBlue, Silver, and United Airlines.

Two Gay Expats - Key West, FL - Gay Hotel - Alexander's Guest House
Alexander's Gay & Lesbian Guesthouse

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.

Two Gay Expats - Key West, FL - Island House - Entrance
Island House Key West
Two Gay Expats - Key West, FL - Island House - Heated Pool - Cafe View
Heated Pool
Two Gay Expats - Key West, FL - Island House - Cafe - Bar Seating
24-Hour Bar
Two Gay Expats - Key West, FL - Gay Hotel - Island House Resort - Clothing Optional Sun Deck
Pre-renovated Sundeck
Two Gay Expats - Key West, FL - Island House - Sun Deck
Renovated Sundeck
Two Gay Expats - Key West, FL - Island House - Outdoor Jacuzzi
Outdoor Jacuzzi
Two Gay Expats - Key West, FL - Island House - Locker Room
Locker Room
Two Gay Expats - Key West, FL - Island House - Gym
Fitness Center
Two Gay Expats - Key West, FL - Island House - Gang Shower
Gang Shower
Two Gay Expats - Key West, FL - Gay Hotel - Island House Resort - Steam Sauna Jacuzzi
Pre-renovated Spa Area
Two Gay Expats - Key West, FL - Island House - Indoor Jacuzzi
Renovated Spa Area
Two Gay Expats - Key West, FL - Gay Hotel - Island House Resort - Un-renovated Room with Private Bath
Un-renovated Room 110
Two Gay Expats - Key West, FL - Island House - Renovated Room - Queen Beds
Renovated Room 108
Two Gay Expats - Key West, FL - Island House - Renovated Room - Bathroom
Renovated Bathroom
Two Gay Expats - Key West, FL - Island House - Trai with Alan at Reception
With Alan at Reception

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.

From a value perspective, we do want to highlight that all rooms come with no resort fees, free coffee and tea, free parking, free happy hour daily, free wifi, and access to all of the 24-hour amenities we discussed earlier. While it’s not inexpensive to stay at Island House, there are lots of included benefits and no hidden fees. We also want to point out that you have to have a human touch point to book directly by calling or emailing. You cannot book online like you can with our other recommended gay or gay-friendly hotels in Key West. While this caught us by surprise on our first stay, it does set the tone for the friendly service and inclusive atmosphere you’ll find at Island House.

For our complete gay hotel review of Island House, check out our most recent Youtube video above!

Two Gay Expats - Key West, FL - Pier House Resort
Pier House Resort & Spa
Two Gay Expats - Key West, FL - Gay Friendly Hotel/Restaurant/Bar/Cabaret - La Te Da
La Te Da Hotel Restaurant Bar Cabaret

Other LGBTQ+ friendly and popular hotels in Key West include Pier House and La Te Da. Trai has so many stories from staying at Pier House as a kid and young adult. Also, the the location cannot be beat at 1 Duval Street.

Also located on Duval Street, adults-only La Te Da is a a hotel, restaurant, bar and cabaret. And all are fabulous! Don't hesitate booking here to enjoy one of the best hotels in Key West. La Te Da boasts an exceptional 9.8 rating on Hotels.com!

Two Gay Expats - Key West, FL - Gay Friendly Hotel/Restaurant/Bar/Cabaret - La Te Da - Restaurant
La Te Da Restaurant

Where to eat and drink – Known as the Conch Republic, Key West is of course known for its fresh local seafood. If you try two things in Key West, you must try Conch as well as Key Lime Pie. The sweet and tart pie reportedly originated in Key West in the late 19th century. Read on for our favorite restaurants in Key West.

Two Gay Expats - Key West, FL - Pepes Breakfast Restaurant
Pepe's Cafe
Two Gay Expats - Key West, FL - Pepe's Breakfast Restaurant - BLT
Breakfast at Pepe's
Two Gay Expats - Key West, FL - Cuban Coffee Queen - Coffee Shop
Cuban Coffee Queen
Two Gay Expats - Key West, FL - Island House - Cafe - Table
Island House Cafe
Two Gay Expats - Key West, FL - Island House - Cafe - Classic Club
Classic Club at Island House
Two Gay Expats - Key West, FL - Conch Fritters - Mallory Square - Sign
Ready for his tasting
Two Gay Expats - Key West, FL - Conch Fritters - Mallory Square
Key West Conch Fritters
Two Gay Expats - Key West, FL - Mermaid Restaurant - Entrance
Thirsty Mermaid
Two Gay Expats - Key West, FL - Thirsty Mermaid Restaurant - Yellowfin Tuna
Yellowfin Tuna at Thirsty Mermaid
Two Gay Expats - Key West, FL - Thirsty Mermaid Restaurant - Dinner
Dinner at Thirsty Mermaid

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.

For lunch, we highly recommend the Island House Cafe. Seriously, all of the food and drinks are excellent here and the team could not be more welcoming and accommodating.

If you are looking for an afternoon snack while exploring Key West, stop at Key West Conch Fritters in Mallory Square. Conch Fritters here are made with tons of sweet conch meat, and also garlic, lime juice, salt and pepper, sweet and hot peppers, flour, and onions. They are then deep fried to a golden brown. Absolutely delicious.

For dinner, Thirsty Mermaid is a local favorite. We like this quaint, romantic spot with mouthwatering delights like Togarashi Spiced Yellowfin Tuna with jasmine rice, wok fried vegetables, and a coconut green chili sauce. Other specialties include fresh local seafood, a selection of Oysters from East & West Coasts, and a full raw bar. They also offer an extensive list of craft beers and wines.

If you are going for a show at La Te Da, we can also highly recommend the hotel's glamorous restaurant. We like to request a table poolside and enjoy their amazing martinis, wedge salads, and fresh homemade pastas. Reservations are highly suggested.

Two Gay Expats - Key West, FL - Gay Friendly Hotel Restaurant/Bar/Cabaret - La Te Da - Randy Roberts - Cher Impersonation
Randy Roberts Cabaret

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.

Two Gay Expats - Key West, FL - Gay Duval Street - Sign
Gay Duval Street
Two Gay Expats - Key West, FL - The 801 Bourbon Bar - Rainbow Crosswalk
Rainbow Crossing
Two Gay Expats - Key West, FL - Gay Hotel - New Orleans House and Bourbon Pub - Entrance - Day
New Orleans House
Two Gay Expats - Key West, FL - Gay Bar - Bourbon St. Pub
Bourbon St. Pub
Two Gay Expats - Key West, FL - Gay Bar - Bourbon St. Pub - Poolside Bar
Poolside Bar at Bourbon St. Pub
Two Gay Expats - Key West, FL - The 801 Bourbon Bar - 801 Girls
801 Girls
Two Gay Expats - Key West, FL - Gay Friendly Hotel/Restaurant/Bar/Cabaret - La Te Da Cabaret
Cabaret Table
Two Gay Expats - Key West, FL - Gay Friendly Hotel/Restaurant/Bar/Cabaret - La Te Da - Randy Roberts
Randy Roberts at La Te Da
Two Gay Expats - Key West, FL - Gay Hotel - New Orleans House and Bourbon Pub - Entrance - Night
Bourbon St. Pub at Night
Two Gay Expats - Key West, FL - Boubon Street Pub - Andy
Waiting for Live Music at The Pub
Two Gay Expats- Key West, FL - The 801 Bourbon Cabaret Drag Show
801 Drag Show Times
Two Gay Expats - Key West, FL - 801 Bourbon - Drag Show
Trai at 801

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.

Finally, Aqua Bar & Club (711 Duval) is a gay bar, club, and performance venue. Given how close all of the gay bars and clubs are on Duval, you can bar hop to find the best crowd for you!


Two Gay Expats - Key West, FL - South Beach Key West
South Beach, the favorite of Tennessee Williams
Two Gay Expats - Key West, FL - Higgs Gay Beach
The very rocky Higgs Gay Beach

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.

Higgs Beach is the main gay beach although we found it quite rocky and unpleasant to spend the day. Maybe its because we live near some of the best beaches in the world in Tulum (Mexico), but we much prefer the pool scene in Key West. It is worth a walk or bike ride to see the Key West Aids Memorial.

Two Gay Expats - Key West, FL - Island House - Massage Cabana
Massage Cabana at Island House

Where to find gay male massage – When you need a break from the sun, Island House offers poolside massages in a private cabana.

Two Gay Expats - Key West, FL - Graffitti - Gay Shopping
Graffitti Key West

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!

Other Services


Two Gay Expats - Key West, FL - Visitors Center - Duval Street
Gay Key West Visitor Center

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!

Two Gay Expats - Key West, FL - KWEST Liquors
KWEST Liquors

Wine/Liquor store – Conveniently located wine and liquor store at 705 Duval Street.

Travel Resources


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.

Two Gay Expats - Key West, FL - Conch Tour Train
Conch Tour Train

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.

Two Gay Expats - Travel Essentials - Universal International Travel Power Adapter
Our Favorite Universal International Travel Power Adapter

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.

Want to see more? For additional footage of our adventures in Key West, check out our Gay Key West and Island House YouTube videos linked above and be sure to smash that like button and subscribe! And, of course, follow us on social media @twogayexpats on your favorite socials for more gay travel inspiration!

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Hi! We're Two Gay Expats
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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