Key West is out there, way out there

Before there were countless destinations where LGBTQ+ travelers could feel free and celebrated, there was Key West. Known as the U.S.’s original gay paradise, Key West was one of the first cities to officially court gay and lesbian tourists—and boy, did it succeed. Today, gay Key West remains a haven for LGBTQ+ travelers, offering a mix of tropical charm, unmatched inclusivity, and endless fun.

What’s not to love? Think beautiful beaches, perfect weather, a vibrant nightlife, and an “anything goes” attitude. It’s a place to relax, unwind, and unapologetically be yourself. Pack light because clothes here? Totally optional—literally, in some places.

The residents of Key West hold dear the island’s two biggest assets: nature and history. Before you even see the water, you’ll stand in awe of the lush greens surrounding the restored old wooden homes and the tropical trees and flowers flourishing in every possible corner. When you see chickens running free in the street and the polydactyl cats (with extra toes) lounging at the famous Ernest Hemingway House, you’ll start to get to the notion that things are different here. The locals live by the motto “One Human Family,” and that sense of acceptance is felt the moment you step onto the island. Everybody fits in.

Three main events highlight the carefree, clothing-optional spirit of Key West. For the gays, the Bone Island Bare It All Weekends take place in July and December. (Cayo Hueso, or Bone Key, was Key West’s original name, but now it just lends itself to not-so-vague puns.) You don’t have to be naked, but you probably should trim the hedges ahead of time in case the mood catches you. Speaking of bushes, the ladies head to Womenfest in September, which ups the class a little with film, live music, and comedy. But still, the ho-ha’s and ta-ta’s come out to play—this is Key West, after all. In October, be prepared for a kaleidoscope of color and creativity at Fantasy Fest. A 10-day, no-holds-barred fête filled with costumes, body paint, drinking, dancing, life loving and skin aplenty leading up to Halloween.

These vibrant celebrations epitomize the essence of Key West—free-spirited, inclusive, and unforgettable. Also, many guesthouses have year-round policies encouraging you to put nothing between you and the sun. You don’t have to, but if you do, remember to apply sunscreen everywhere. Yes, everywhere.

While the vibes on land will keep you fully entertained, the water is where Key West really shines. After all, the island is surrounded by the only living coral reef in the continental U.S. As you can imagine, Key West boasts tons of options for watersports (not that kind). Popular activities include snorkeling, kayaking, paddleboarding, and sunset cruises. For a laid-back beach day, check out Higgs Beach or Fort Zachary Taylor State Park, where you can picnic, snorkel, or simply soak up the sun.

On land, walking or biking make perfect daytime activities, and the stunning Key West sunset is a must-see, especially from Mallory Square. The street performers there keep the crowd entertained with or without the glorious sun. From antique shopping to theater to cafes to bars and clubs, Duval Street earns the reputation for the everything-gay place. You’ll eat, drink, and dance yourself into giddy fervor. Savor local favorites like Cuban sandwiches, fresh seafood, and (of course) authentic key lime pie. Then watch the sunrise, sleep a bit, and do it all over again.

Key West brings its A-game when it comes to gay-friendly accommodations. From charming guesthouses to all-male nude resorts, there’s something to match every vibe. Highlights include Island House (an iconic all-male resort), New Orleans House (for a clothing-optional escape), and Alexander’s Guesthouse (a chic LGBTQ+ property equipped with inclusive hospitality). For those seeking luxury, resorts around Duval Street or near the Harbor Walk offer prime sunset views and upscale perks.

Whether you’re partying until sunrise, sipping cocktails by the pool, or snorkeling along the coral reef, Key West never dies down; even the off-season is likely to be wilder than you’ll see at home. This tropical paradise is more than just a getaway—it’s a place where freedom, acceptance, and joy reign supreme.

No matter how wild (or chill) you want your trip, you’ll find it all in gay Key West. PACK. LIGHT. And get ready to leave your worries—and maybe your clothes—behind.

Photos by JoeSwickFoto and Jim Werner and courtesy of the Florida Keys News Bureau