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Three days in Key West: Old Town and Duval Street, Higgs Beach, drag bars and the gay guesthouses, plus how to get to the end of the Overseas Highway.
Key West sits at the end of the Overseas Highway, about 160 kilometres southwest of Miami and closer to Cuba than to Florida's next big city. The island is small, and you can walk its historic core in a couple of days. Gay visitors have been part of island life here for decades, and you feel it in how relaxed people are with one another. For a first look at the neighbourhoods, addresses and dates, the Gay Key West Guide is a good place to start. Three days is enough to combine Old Town, the beach and the nightlife without cramming the trip.
Day 1: Arriving and Old Town
The heart of the island is Old Town, built around Duval Street, which runs straight across from one coast to the other. Bars, galleries, shops and restaurants line the street, many of them in the classic wooden Conch-style houses. A first walk helps you get your bearings and settle into the island's pace. The queer scene clusters at the eastern end of Duval Street, where many of the well-known addresses sit close together.
If you're coming from Europe, you've had a long day, since there are no direct flights to Key West. Take the first evening slow. Sunset at Mallory Square makes a good opener, where locals and visitors gather for the nightly mix of street performers and vendors. After that, one drink is enough to get a feel for the scene. For more ideas on settling into a new place without forcing it, the notes on finding the scene in a new city are worth a read before you go.
Day 2: Beach and Island Life
Key West isn't a classic beach island; much of the shore is rock and mangrove. The largest public beach, Smathers Beach, lies to the south and is long and well kept. Gay visitors tend to prefer Higgs Beach near the centre, though, because it's more central and the stretch in front of it has long been a community meeting spot. You can rent loungers and umbrellas there, and cafes and a pier are within walking distance.
If you'd rather not spend the whole day by the water, there's more of the island to see. The Ernest Hemingway House with its six-toed cats, the southernmost point marker in the continental US, and the old harbour are all easy to reach on foot or by bike. On such a flat island, a rental bike is the most practical way to get around. In the evening, dinner in Old Town is the obvious move, from seafood to a slice of classic Key Lime Pie for dessert.
Day 3: Going Out and Nightlife
Start the third day slowly and give it over to the nightlife. Almost all the gay bars sit at the lower end of Duval Street, within walking distance of each other. The mood ranges from an open-air bar to spots with drag shows to a dance floor. Since many of the buildings have several levels and courtyards, an evening can stretch on for hours inside a single block.
Drag has a long history in Key West, and several venues run shows every night. Weekdays are quieter, and the island fills up noticeably on weekends. Build in enough breaks during the day so you've got the reserves for the evening. The island also runs a busy events calendar, with Pride in June and the costume-heavy Fantasy Fest in late October drawing the biggest crowds; if your trip lines up with one of those, book well ahead.
Where to Stay
Key West has one quirk when it comes to where you stay: several guesthouses cater specifically to gay visitors, many in historic wooden houses with a pool and a courtyard. They tend to cluster in Old Town, close to the bars, and the supply is limited, so it goes fast in high season. Book early. If you want to weigh the signals that tell a genuinely welcoming place apart from marketing, the guide on spotting gay-friendly hotels and avoiding pinkwashing covers what to look for.
Practical Tips for Getting There
There are two ways to arrive. Key West International Airport is served through US hubs like Miami or Atlanta, with no direct flights from Europe. The alternative is the drive along the Overseas Highway, one of the best-known scenic roads in the country, which crosses dozens of bridges from island to island. From Miami that's a good three to four hours, depending on traffic. On the island itself you won't need a car; much of it is walkable, and the rest is a quick ride by bike or scooter.
The best time to travel is between December and April, when the weather is warm and dry. Late summer and autumn can get muggy, and that window also falls in the Atlantic hurricane season. If you're pairing Key West with the mainland, Gay Fort Lauderdale in 3 days works as a natural add-on before or after, and you can sketch out the wider trip with the city trips overview. Three days are enough to get to know Key West without running it like a schedule. With more time, you can stop on one of the other Keys on the way back, or fold in a few days in Miami or Fort Lauderdale.
