There’s exactly one road to Key West, and that’s the whole point.
Highway 1 — the Overseas Highway — runs 113 miles from Miami to Mile Marker 0, bridge after bridge, the Atlantic on one side and the Gulf on the other for the last hundred miles. No detours, no alternate routes, no one to negotiate the pace with but yourself. It’s the single most iconic drive in Florida, and it might be the one destination in this state that’s genuinely better alone — no passenger to keep entertained, no compromise on when to stop, and a soundtrack entirely your own for the length of a very long bridge.
This is the itinerary from Florida: The Complete Solo Traveler’s Guide, on sale October 5 — the exact six-day version built specifically for a driver traveling by themselves.
Day 1: Miami to Islamorada
Rent a car in Miami and head south on US-1. On day one, the temptation is to push straight through to Key West, but the drive has a stop worth making: Robbie’s Marina in Islamorada, at Mile Marker 77.5. Pay a small fee to walk the dock, another for a bucket of bait, and hand-feed tarpon that can run six feet long as they lunge out of the clear water beside the pilings. It’s strange, it’s memorable, and it’s over in under an hour — exactly the kind of stop a solo traveler can make on a whim without checking with anyone.
Day 2: Marathon and the Lower Keys
Most Highway 1 road-trippers treat the stretch between Key Largo and Key West as something to get through. That’s exactly why it rewards someone willing to slow down. The Turtle Hospital in Marathon runs guided tours of a genuine working veterinary hospital for injured sea turtles — educational rather than a roadside gimmick, and one of the better rainy-day options in the entire Keys. In the afternoon, Bahia Honda State Park, just north of the Seven Mile Bridge, has three real beaches on clear, shallow water — rare in the Keys, where most “beaches” are narrow and people-made. Continue to Key West by evening.
A note on the drive itself: the Seven Mile Bridge, roughly at the route’s midpoint, deserves a deliberate stop rather than a drive-through. Pull off at either end for the view, then continue on.
Days 3-5: Key West
This is where the car gets to sit still for three days. Old Town is barely four miles long and two wide — flat, walkable, and small enough that the same handful of faces start showing up at the same handful of bars until strangers start to feel like regulars. That’s not an accident of the itinerary; it’s the actual mechanism by which Key West works for someone traveling alone.
- Day 3: Mallory Square at sunset, then a bike rental to cover the island the way it’s meant to be covered.
- Day 4: the Hemingway House, the Key West Cemetery, and a sunset sail out of the historic seaport.
- Day 5: a slower close — the Southernmost Point at sunrise, the Key West Butterfly Conservatory, and dinner at B.O.’s Fish Wagon.
Duval Street gets the crowds and the bachelorette parties. The real Key West — the quiet lanes of Conch-style shotgun houses, the chickens that legally own the sidewalks, the paddleboard rental shack that’s really just a guy named Skip and a cooler — is one block off in any direction. Go find it.
Day 6: The Return Drive
Drive back north more slowly than the way down. Miami International or Fort Lauderdale-Hollywood both work well for a next-morning departure, which means the final night in Key West doesn’t have to end early.
Why This Drive Works Alone
Solo road trips live or die on flexibility. Highway 1 hands you more of it than almost anywhere else in Florida. There’s no group pace to match on the bridges. No vote required on whether to stop at the Turtle Hospital or skip it. And the destination at the end — Old Town’s bar-stool culture — is genuinely built for a party of one. Few 150-mile stretches in the country pack in this much range along a single, unbroken line of pavement.
The full write-up is in Florida: The Complete Solo Traveler’s Guide, on sale October 5. It includes walkability and night-safety ratings for every stop. A “Table for One” recommendation in each town. And the complete Skip-or-Spend verdicts on Robbie’s, the Turtle Hospital, and everything in between. Want the deeper dive on Key West itself? See the full Key West guide — it covers the Conch Republic’s strange history and where to eat solo without a second thought.
Pre-order the book now on the GoingSolo.Life bookstore page — available everywhere books are sold October 5.
read alone, travel alone —
Ready to Go? Grab Your Guide.
Hour-by-hour itineraries built for independent travelers.
Free 48-hour guides, safety guides, and interactive maps — every city.
