Key West LGBTQ+ Travel Guide: Drag, Sunsets & Gay Poolside Shenanigans at the End of the Road 🏳️‍🌈🌴

Welcome to the end of the road—literally. U.S. Route 1 finishes its 2,369-mile journey here, in Key West, Florida. But for LGBTQ+ travelers? This is where the adventure really begins.

Key West, the southernmost point in the continental U.S., isn’t just a tropical escape. It’s a sun-drenched, queer-as-hell paradise that’s been welcoming LGBTQ+ visitors for decades with its laid-back charm, historic flair, and anything-goes energy.

Pastel cottages, wandering chickens, drag queens high-kicking on Duval Street, and sunsets so breathtaking they get their own nightly celebration (with mojitos, obviously).

You can spend your days snorkeling coral reefs or biking through Old Town’s rainbow-flag-lined streets, and your nights sipping mojitos at Aqua or catching a drag show at 801 Bourbon Bar.

This island has long been a haven for queer artists and eccentrics—from Tennessee Williams to Elizabeth Bishop—and today, it’s just as vibrant. Gay bars? Check. Gay guesthouses? Plentiful. Pool parties? Let’s just say we stayed hydrated.

Getting to Key West:

You can fly directly into Key West International Airport (EYW), but many travelers opt for the scenic 3.5-hour drive from Miami—over 40+ bridges and turquoise waters. It’s one of the most iconic road trips in America, and yes, the drive is worth it… especially the last leg.

Best Time to Visit:

High season runs from December to April, with perfect weather and big events like Fantasy Fest and New Year’s Eve. For Pride, come in early June. For a steamier scene, Tropical Heat (August) and Womenfest (September) turn up the heat.

Key West Pride lands in late June and is refreshingly unpretentious—think pool parties, dance cruises, and a big ol’ parade down Duval. Also worth planning for: Tropical Heat in August and Womenfest in September, both turning the island into one big, sweaty, sexy queer lovefest.

What to See & Do:

Duval Street – The beating heart of gay Key West. Bar-hop from 801 Bourbon Bar (drag shows nightly) to Aqua (more drag, more glitter) to 22&Co. (even more glitter) to Bourbon St. Pub (men in barely-there/not-actually-there swimsuits and a pool in the back).

Fort Zachary Taylor State Park – Locals love this beach for its chill vibe and crystal-clear water. Pack a picnic, bring a towel, and prepare to make some new friends under the palms. There is a fee to get in though.

Island House – Even if you're not staying here, get a day pass for $50. This legendary all-male, clothing-optional resort has a pool, hot tub, sauna, and a vibe that’s equal parts steamy and social. Pool parties Sundays and Wednesdays.

Graffiti Key West - Need a last-minute swimsuit, something sexy for the pool party, or just ran out of lube? Head to Graffiti, Key West’s go-to gay store for all the essentials—and then some. Bonus: you can snag a free copy of Q Magazine while you’re there to get the scoop on what’s happening around town.

Sunset Celebration at Mallory Square – Head here any evening before dusk. Street performers, food carts, live music, and one of the most iconic sunsets in the U.S.

Drag Shows – This town punches way above its weight when it comes to drag. Don’t miss the hilarious cabaret at Aqua or the raunchy realness at 801 Bourbon.

Snorkeling or a Gay Sunset Cruise – Explore coral reefs or just sip champagne with shirtless strangers as the sun goes down. Try Blu Q or FURY for LGBTQ-friendly options.

Key West AIDS Memorial – A poignant, beautifully designed tribute at the White Street Pier honoring those lost to HIV/AIDS in the Keys. Worth a quiet moment of reflection.

Gallery Strolling – The island’s art scene is low-key fabulous. Check out galleries along White Street and in Old Town for queer and local artists making colorful, beachy magic.

Where to Eat & Drink:

Blue Heaven – Iconic Key West brunch spot with roosters roaming the patio, live music, and mile-high Key lime pie that will ruin all others for you. A lot of people go for brunch (get the pancakes) but dinner is fabulous (get the yellowtail snapper).

Lola’s Bistro - One of Key West’s most intimate and buzzed-about dining spots—and for good reason. There are only a handful of tables, a menu that changes nightly, it’s BYOB, cash only, and reservations are an absolute must. But it’s worth the effort. Thank you to the guys at Fagabond for this A+ recommendation.

Garbo’s Grill – A food truck featured on Diners, Drive-Ins, and Dives. Tucked behind a bar (hello, divey magic) serving up killer Korean BBQ tacos, poke bowls, and burgers. Casual, queer-friendly, and consistently delicious.

Latitudes – Want romance? Book a sunset dinner on a private island just offshore (via boat ride from the Opal Key Resort). Upscale seafood, ocean views, major proposal energy.

Little Pearl – A hidden gem with a daily-changing menu of fresh, elegant seafood in an intimate setting. Perfect for a quieter date night.

Moondog Café – Cute, artsy vibes with strong coffee, great pastries, and a solid breakfast if you find yourself in need of post-party recovery.

Where to Stay:

Island House – The gold standard for gay male travel. Clothing-optional, 24-hour pool and bar, steam room, and a famously welcoming vibe. Day passes available if you're not overnighting. Wild pool parties Sundays and Wednesdays.

Alexander’s Guesthouse – LGBTQ+ owned and operated boutique hotel that’s mixed gender, beautifully styled, and full of charm. Gorgeous pool, fab breakfasts, and located on a quiet block just off the action.

The Mermaid & The Alligator – A stunning gay-owned B&B with lush gardens, luxurious rooms, and a name that sounds like a fairytale. Ideal for couples looking for something a bit more tranquil.

New Orleans House – Smack-dab on Duval above Bourbon St. Pub. Loud, cruisey, central, and perfect if you want to stumble home after the bars.

Kimpton Fitch Lodge or Ella’s Cottages – For something low-key, chic, and LGBTQ+-friendly but not explicitly gay. Great value, stylish interiors, and a little more of a “staycation” vibe.

Some upcoming events:

Conch Republic Independence Celebration
📅 April 18-27, 2025
A whimsical week-long festival commemorating Key West's "secession" from the U.S., featuring parades, parties, and the famous "World's Longest Parade."

Key West Pride
📅 June 22–29, 2025
This week-long celebration features a variety of events, including pool parties, drag shows, and a vibrant parade down Duval Street.

Tropical Heat
📅 August 13–17, 2025
Tropical Heat is a 5-day event tailored for gay men, featuring themed parties, pool gatherings, and adult-oriented entertainment. ​

Womenfest
📅 September 3–7, 2025
Womenfest is one of the largest lesbian gatherings in North America, offering a range of activities from pool parties to art exhibitions, all celebrating women.

Fantasy Fest & the Headdress Ball
📅 October 17–26, 2025
A world-famous 10-day costume and masking festival with parades, street fairs, and themed parties. As part of the Fantasy Fest, the Headdress Ball is a premier LGBTQ+ event featuring extravagant costumes and performances.

New Year's Eve Celebrations
📅 December 31, 2025
Ring in the New Year with unique island-style celebrations, including the famous "Red Shoe Drop" at Bourbon Street Pub.

Whether you’re chasing sunsets, dancing under the stars, or just soaking up that anything-goes island energy, Key West is the kind of place that leaves a mark—salty, sweaty, and soul-nourishing in the best possible way. Ready to plan your queer escape to the end of the road? Pack your shortest shorts, your sassiest shades, and get down there. The mojitos are waiting.