Welcome to the most-photographed butt plug in America! The Southernmost Point Buoy is a giant, striped concrete icon marking the southernmost point of the contiguous states and the “almost-Cuba” spot just 90 miles from Havana—and yes, everyone and their drag mother takes a photo here. It’s pure kitsch, but it’s Key West canon, so set that alarm and snap your pic at sunrise before the cruise ship crowd descends. Bonus: it’s walking distance from other faves like the Hemingway House and Fort Zach—so you can keep the gay history tour going.

Sunset in Key West isn’t just a vibe—it’s a full-on spectacle, and Mallory Square is ground zero for the daily drama. Think magicians, psychics, fire jugglers, and ukulele-strumming weirdos, all gathering to worship the big flaming ball in the sky as it dips into the Gulf. It’s part street party, part spiritual experience, and all about that golden-hour selfie. If you leave Key West without catching at least one sunset here, did you even go to Key West?

Ready to ditch your clothes and dive into the turquoise waters of Key West? The Blu Q catamaran offers clothing-optional adventures like snorkeling, kayaking, and sunset cruises, all set in the crystal-clear waters about 10 miles west of Key West. You’ll encounter sea turtles, sharks, and other marine life while soaking up the sun (or not, it’s up to you). Blu Q also hosts romantic sunset sails and fun day trips to sandbars, offering the perfect blend of relaxation and socializing. If you’re looking to explore Key West’s beauty au naturel, this is the only all-gay, clothing-optional charter in town—where the breeze is just as breezy as your vibe.

Key West Cemetery is a must for fans of the weird and wonderful. Wander among quirky epitaphs like “I told you I was sick” and “Devoted fan of Julio Iglesias,” or explore legends like the ghost of Elena Hoyos, whose body was famously stolen and preserved by a lovesick necrophile. With spooky statues, pet tombs, and restless spirits, this historic graveyard is equal parts haunting and hilarious.

President Truman spent 175 days at this tropical escape, turning Key West into his winter White House. He fished, met with world leaders, and ruled from a gay little island—while his administration sparked the Lavender Scare back home. History: it’s complicated.

Tour the lush, sun-dappled home where Hemingway lived, wrote, and brooded for a decade—surrounded by six-toed cats and complicated masculinity. You’ll see his typewriter, his garden, and maybe ponder his, ahem, layered relationship with queerness. It’s Key West canon, darling.

Manmade? Maybe. But Smathers Beach serves the real deal with half a mile of soft sand, palm trees, and every water sport your little sunburned heart desires. Come for the spring break energy, stay for the calm waves and glistening Instagrams.

Higgs Beach brings the drama—long pier, ocean views, and watersports galore. Take a break in the dreamy orchid-filled gardens next door, then refuel at Salute!, where the cocktails hit as hard as the sun.

Key West is one of the most haunted places in America—and not just because your ex is vacationing here. Join a ghost tour, meet Robert the Doll (he’s iconic), and explore haunted firehouses, bars, and cemeteries with locals who know the spirits by name. You’ll scream, you’ll laugh, you might even haunt a little yourself.

Nicknamed Fort Liz Taylor Beach by locals, this 54-acre state park is the most beloved stretch of gay-friendly shoreline in Key West. Sun, shade, Speedos—and yes, Elizabeth Taylor really did hang here with Richard Burton. It’s worth the small entry fee, if you don’t mind a few rocks with your queer paradise.