You don’t need to book an airline ticket to experience an unforgettable tropical vacation. Key West, Florida’s most tropical travel destination, is easily accessible by one of the most stunning drives in the country–the Road to Paradise. As you drive down the famous seven-mile bridge along the route, taking in miles of marine wildlife and local color, you’ll feel the island vibes start to set in.
There are so many reasons to love Key West. While its gorgeous white sand beaches, crystal clear waters, historic architecture, and thriving LGBTQ community alone make it worth a visit, we love Key West for its endless supply of outdoor activities and nightlife.
Gay Night’s Stay
When looking for a place to stay in Key West, we recommend the Guesthouse District. This conveniently located cluster in Old Town hosts a fabulous array of accommodations that feel much more like a “home away from home” than an impersonal hotel brand.
Resorts such as the clothing-optional Island House are famed by gay travelers from across the globe. Others flock to the friendly, historic, wood-clad La Te Da Hotel, home to a lively Sunday Tea Dance. We also love the historic Alexander’s Guesthouse, Equator Resort, or New Orleans House. All are based in Old Town and offer a friendly, personalized welcome.
Fuel up and go
If you like your cup of coffee with a side of people-watching, check out Keys Coffee Co. on Duval Street. It takes its roasting very seriously, serving up a variety of classic coffee beverages, nitro cold brew, and iced coconut breve, a local favorite.
There’s also the iconic, waterfront Cuban Coffee Queen, famed just as much for its eye-catching ‘Key West’ mural that absolutely everyone uses as a background for selfies. It’s the perfect place to grab an iced café con leche and “Caliente Cuban Mix” sandwich.
Need something quick and easy? Head to Baby’s Coffee. Known for their in-house roasted coffee and amazing bagels, this quirky market is a great place to grab food, coffee, and wine (the essentials) before hitting the beach.
Suns out, buns out
An afternoon at the beach is a must-do when visiting Key West.
Key West is 4 miles by 2 miles in size, so you never have to go far to enjoy some sand and surf. Not far from Higgs, a popular gay beach, is Fort Zachary Taylor State Park, near the southernmost point of the key. Besides the beach, you’ll find nature trails and the ruins of a historic fort to explore.
If you want to take your fun offshore, book an all-male snorkeling trip with Blu Q. They also host clothing-optional day trips, for those who hate tan lines, and evening sunset cruises.
For adrenaline junkies
Want to take your appreciation for Key West to new heights? Get a great view of the island, and a serious kick of adrenaline, on a skydive. From this perspective, you’ll see crystal blue oceans and coral reefs teeming with life.
If you’re afraid to take the leap alone, try jumping into paradise on a tandem skydive. You’ll be strapped in with an expert, giving you some peace of mind. Focusing on safety first, Skydive Key West is consistently rated one of the top ten places in the world to experience skydiving.
When you come back to earth, your adrenaline’s bound to be high. Carry that energy into the evening partying on Duval Street.
Where to meet on Duval Street
Duval Street is easily the most happening part of Key West. lined with colorful shops, restaurants, galleries, bars, and nightclubs, you’ll find everything you need on this cozy thoroughfare. You’ll find a celebration of that in galleries along Duval Street, like Tucker’s Provisions, Effusion Gallery, and Mel Fisher’s Treasures.
At the heart of the gay nightlife scene, where Petronia Street meets Duval, Key West’s rainbow crosswalks beacon you to a wild night out. Long-running gay favorites include 801 Bourbon Bar, home to Sushi and the 801 Girls, and the local-friendly, dive-ish Bobby’s Monkey Bar.
Next door to 801 you’ll find cruisy fun at leather club One Saloon, while Aqua offers more drag cabaret and dance tunes in a club setting. The biggest late-night destination is probably Bourbon Street Pub, with its army of go-gos lighting up a men-only garden bar and outdoor pool area.
People fall in love with Key West because almost everyone who visits experiences the “one human family” spirit that glues the community together.
There’s also a certain, almost indescribable magic in the air. That magic can look like meeting a celebrity at a local bar and chatting with them until the last call, a simple stroll through Old Town and finding a residence of one of your favorite authors, or spotting a manatee while kayaking in the mangroves.
Almost everyone experiences something special when they come to Key West, and that’s why they come back.