In the game
Let’s be straight: Rockstar hasn’t shown a Key West. The Leonida Keys in Trailer 2 and the Extended Look are bridges, water, canal homes and bars, and the road clearly goes somewhere, but nobody outside Rockstar knows what’s at the end of it. This page is a travel idea, not a fact about the game.
What we can say is that the Leonida Keys look like they draw on the whole real chain, and the real chain ends at a town that has more GTA energy per square foot than anywhere in Florida: a party street, a harbor of dubious boats, sunset rituals, roosters, a lighthouse and a hundred years of smugglers. If you’re driving the Keys because of the game, you’ll end up here, and you should.
The real place
Key West was Florida’s richest city in the 1800s on the back of shipwreck salvage, then cigars, then sponges, then the navy. The railroad arrived in 1912 and the highway in 1938, Hemingway lived here through the 1930s, and the town has spent the decades since being a slightly disreputable place people run away to.
Duval Street runs a mile and a bit from the Gulf side to the Atlantic side and is the spine of it all: open-front bars, drag shows, T-shirt shops, a Cuban coffee window every block. The detail a GTA fan will recognize is the mix of grand old wooden houses with wraparound porches, tin roofs and gingerbread trim on one block and total chaos on the next. It’s a real town of about 25,000 residents, chickens included, and it wears the tourism lightly.
Go there
The classic day: park once (a garage or your hotel, because street parking is a trap) and do everything on foot or by rented bike. Morning at the Ernest Hemingway Home and Museum on Whitehead Street, where the six-toed cats still run the place, then the Key West Lighthouse across the road for the view. Take the photo at the Southernmost Point buoy early, because the line grows all day. Afternoon at Fort Zachary Taylor, the best beach in town, or on a snorkel boat out to the reef.
Sunset is a ritual at Mallory Square, with street performers, a crowd and the schooners crossing the sun. Then Duval. Sloppy Joe’s has been there since 1933 and is exactly as loud as you’d hope; the smaller bars on the side streets are where the locals are.
One honest warning: Key West is expensive and it books up. Rooms in winter can run well over $300 a night and the decent ones go months ahead. If the budget is tight, stay in Marathon or Big Pine and drive in for the day; the last 45 minutes of the Overseas Highway are half the fun anyway.
Nearby
- Seven Mile Bridge: the big set piece of the drive, an hour back up the road.
- Bahia Honda State Park: 40 minutes up the road, the beach Key West doesn’t really have.
- The Overseas Highway: everything about Key West is better if you’ve driven the whole road to get there.
Updated September 12, 2026. Spotted an error? Tell us.