Gay Holidays to Key West
Gay Holidays to Key West
A little slice of rainbow paradise at the southernmost tip of the USA, gay holidays to Key West are about freedom, fun and fabulousness. With turquoise waters, quirky charm and an LGBT+ spirit that runs deep, this island is a proud haven for queer travellers.
Laid-back and loud, sun-kissed and subversive—Key West doesn’t just welcome LGBT+ visitors, it was built by them. If you’re seeking a destination that’s as camp as it is cool, look no further.
Island Living With a Queer Twist
Key West combines Caribbean vibes with Floridian flair, wrapped up in a town that feels more like a community than a city. Colourful clapboard houses, chickens roaming the streets, drag queens on bicycles—this isn’t a dream, it’s just another day in paradise.
It’s also been an LGBT+ safe haven for decades, attracting artists, activists and adventurers. Today, it proudly wears its reputation as one of the most queer-positive places in America.
Top Things to Do on a Gay Holiday to Key West
Yes, you can party. But Key West also feeds your soul—with sunshine, sea, and stories worth telling.
- Sunbathe at Higgs Beach or Fort Zachary Taylor Beach, both known for LGBT+ crowds
- Catch the sunset celebration at Mallory Square – street performers, cocktails and community
- Tour the Ernest Hemingway House, home to six-toed cats and queer literary energy
- Wander colourful Duval Street, lined with rainbow flags and palm trees
- Join a drag brunch, ghost tour, or eco-sailing trip – this island has layers
Everything is close by. Everything is walkable. And nothing is too serious—unless you want it to be.
Key West LGBT+ Nightlife: Campy, Casual and Iconic
The scene in Key West is vintage queer with a tropical twist. Most of the action happens around Duval Street, and you won’t need taxis—just your flip-flops and a sense of humour.
Top picks:
- Aqua Bar & Nightclub – home of the Aquanettes drag show (expect feathers and fierce lip-syncs)
- Bourbon Street Pub – part bar, part gay guesthouse, all attitude
- 801 Bourbon Bar – a camp cabaret vibe with top-tier drag talent
- Saloon 1 – a leather and Levi’s dive bar with regular events and a loyal local crowd
- La Te Da – cocktails, cabaret, and Sunday tea dances in an elegant setting
In Key West, the line between nightlife and day life blurs beautifully.
Key West Pride and Annual Queer Events
Key West has more pride than it knows what to do with. And that’s a good thing.
Key West Pride is held each June and includes:
- Parades and pool parties
- Drag races down Duval Street (literally, in heels)
- Sunset sails and street fairs
- The Rainbow 5K and Mr/Miss Pride competitions
Other events include:
- Womenfest (September) – a huge celebration for queer women and non-binary folk
- Key West Bear Weekend
- Fantasy Fest (October) – outrageous costumes, body paint, and anything-goes energy
Every month is Pride month here—just with different accessories.
LGBT+ Rights and Safety in Key West
While wider Florida politics may feel uncertain, Key West is its own world—and proudly so. Local government, businesses, and residents fiercely support LGBT+ rights and visibility.
Same-sex marriage is legal, gender expression is respected, and public affection is completely normal. You’ll see rainbow crossings, inclusive signage, and drag queens leading community events.
As always, be aware of your surroundings, but know this: Key West is one of the safest, most accepting places you can visit as an LGBT+ traveller.
Why Book With Wide Awake Holidays?
At Wide Awake Holidays, we believe that “sometimes gay-friendly isn’t friendly enough.” In Key West, it’s not about blending in—it’s about standing out with pride.
Here’s what you get when you book with us:
- Full ATOL protection and Protected Trust Services
- Tailor-made itineraries that include boutique gay guesthouses, eco-adventures, nightlife and more
- Access to unique local tours with queer hosts and performers
- Always included: Supplier Failure Insurance and Scheduled Airline Failure Insurance
- Friendly, inclusive service from people who understand what queer travel really means
From snorkelling to sequins—we’ll help you do Key West your way.
Ready for Palm Trees and Pride?
Gay holidays to Key West are the antidote to ordinary. Whether you’re sunbathing in rainbow swimwear, sipping mojitos with drag royalty, or soaking up queer history on a tropical breeze—this island has you.
Tell us your vibe, and we’ll turn it into the queer island holiday of your dreams.