Most people assume a Keys trip means a hotel in Key West. It doesn’t have to. The Keys are a chain of islands strung along one road, and each one has its own character. Basing further up shortens the drive, usually costs less, and puts you closer to the water.
I’ve made the drive from Miami close to a dozen times. Here’s how I’d choose.
Want a plan like this for your trip?
Key Largo: closest to Miami
Key Largo is the first big key you hit coming south, so it’s the easiest weekend from Miami. It’s a great jumping-off point for fishing trips and local boat tours.
Best for: a short weekend, or if you want to be on the water more than in a town.
Islamorada: fishing and Key lime pie
Islamorada is a great place to sleep and eat, and it sits roughly in the middle of the whole chain. If you only base in one place and want to explore both directions, this is it.
Marathon: halfway down
More fresh fish, more island-time vibes. Marathon puts you within easy day-trip range of Key West without paying Key West prices every night.
And Key West itself
If you do stay in Key West, Duval Street is where you stay and where you play. What surprises people is the scale: you’re never more than about fifteen minutes from anywhere else on the island, which is why the pace drops the moment you park.
Two things that make or break the trip
- Leave early, both ways. There’s only one road. Traffic heading north builds through the afternoon, and when it backs up there’s no alternative route.
- Book Dry Tortugas ahead. It’s about 70 miles west of Key West and reachable only by ferry or seaplane, and both need reservations. Plan to give it most of a day.
My full four-day version of this drive, with the stops in order, is here: Miami to Key West. Want it built around your dates? Book a free 20-minute call.
Dry Tortugas details: National Parks Traveler.