You’re probably thinking it’s just one long road. I mean, technically, it is. But if you just punch "Key West" into your GPS and mindlessly follow the blue line, you are going to miss the entire point of the trip. Driving the 113 miles from mainland Florida to the Southernmost Point is less of a commute and more of a psychological transition. You're leaving the frantic energy of Miami behind and entering a world where "island time" isn't just a tacky phrase on a souvenir t-shirt—it’s the law.
Honestly, the directions to Key West are deceptively simple: find US-1 and head south until you literally cannot go any further without driving into the Caribbean Sea. But there are nuances. There are drawbridges that can ruin your afternoon, speed traps that will empty your wallet in Big Pine Key, and specific lanes you need to be in before you even leave Florida City.
If you're starting from Miami International Airport (MIA), don't just take the surface streets. You want the Florida Turnpike South. It's a toll road, yeah, but it saves you from the nightmare of stop-and-go traffic on the northern end of US-1. Follow the signs for Homestead and Key Largo. Eventually, the Turnpike just... ends. It merges directly into US-1 in Florida City. This is your last chance for "normal" prices on gas and groceries. Once you hit the 18-mile stretch, prices jump.
The Choice: Card Sound Road vs. The Stretch
Right around Florida City, you have a choice to make. Most people stay on US-1, often called "The Stretch." It’s eighteen miles of paved road with a concrete barrier. It’s fast. It’s efficient. It’s also kinda boring.
If you want the "local" experience, look for the turn-off for Card Sound Road (County Road 905A). It’ll cost you a small toll at the bridge, but it takes you through the mangroves and past Alabama Jack’s. That place is a dive bar legend. Get the conch fritters. It adds about 15 to 20 minutes to your trip, but it feels like the Keys are supposed to feel—wilder, saltier, and a bit more neglected in the best way possible.
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Eventually, both roads converge in Key Largo at Mile Marker 106. In the Keys, nobody uses street addresses. Everything is Mile Markers (MM). The numbers go down as you get closer to Key West. If someone tells you a restaurant is at MM 82, you just look at the green signs on the side of the road. It’s foolproof.
Navigating the Middle Keys and the Seven Mile Bridge
Once you’re through Key Largo and Tavernier, the islands start to get narrower. You’ll see water on both sides. This is where the directions to Key West get spectacular. You'll pass through Islamorada, the "Sport Fishing Capital of the World." Watch your speed here. The local cops do not care that you’re on vacation; they will pull you over for doing 50 in a 45.
The real centerpiece of the drive is the Seven Mile Bridge. It starts around MM 47, just south of Marathon.
Driving this bridge is a surreal experience. It’s just you, a thin ribbon of concrete, and the transition from the turquoise Gulf of Mexico on your right to the deep blue Atlantic on your left. To your right, you’ll see the Old Seven Mile Bridge. It’s a rusted, beautiful relic of Henry Flagler’s Over-Sea Railroad. Parts of it are open to pedestrians and cyclists, leading to Pigeon Key. If you have the time, stop at the 64-acre island under the bridge. It’s a time capsule of 1900s Florida history.
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Why Big Pine Key is the Danger Zone
After the bridge, you hit the Lower Keys. It feels different here. It’s more rural, more residential, and significantly more protected. This is the National Key Deer Refuge.
The speed limit drops to 45 mph during the day and 35 mph at night. Follow this exactly. The Key Deer are tiny—about the size of a large dog—and they have zero road sense. They will walk right out in front of your rental car. Because they are an endangered species, hitting one is a legal nightmare, and the fines for speeding in this zone are astronomical. Just set your cruise control and breathe. You're almost there.
Entering Key West: The Final Approach
As you approach MM 5, the road widens. You’ll cross the Cow Key Channel Bridge, and suddenly, the wilderness is gone. You’re in Key West.
Now, this is where the directions to Key West get tricky for first-timers. Most people naturally stay on US-1, which becomes Roosevelt Boulevard. It loops around the island. If you stay on North Roosevelt, you’ll pass all the big "big box" stores and chain hotels. It’s the commercial side of the island.
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If you want the scenic entrance, stay in the left lane as you enter the island and take South Roosevelt Boulevard. This takes you past Smathers Beach. You’ll see the palm trees, the ocean, and the paragliders. It’s a much more "vacation-y" way to arrive. Both roads eventually lead to the Historic District (Old Town), which is where the famous bars like Sloppy Joe’s and the Ernest Hemingway Home are located.
Parking is the Final Boss
You’ve made it. You followed the directions, saw the water, and didn't hit a deer. Now you have a problem: where do you put the car?
Key West was built before cars existed. The streets are narrow, and parking is a genuine nightmare. If your hotel or Airbnb doesn't offer a dedicated spot, don't try to "find" one on the street in Old Town. Most of those spots are marked "Residential" in white paint on the asphalt. If you park there without a local permit, you will get a ticket or a tow.
Your best bet is the Park-and-Ride at the Old Town Garage on Caroline Street. It’s affordable, and once you park, you can take the Duval Loop bus for free. Honestly, the best way to see Key West is on a bicycle anyway. Rent one and leave the car keys in your room.
Real-World Advice for the Drive
Traffic can be a beast. There is only one way in and one way out. If there’s an accident on the Seven Mile Bridge, you aren't going anywhere for hours. Check the "Monroe County Sheriffs Office" social media pages or use a live traffic app before you leave the mainland. Friday afternoons heading south and Sunday afternoons heading north are the worst times to travel.
Also, don't sleep on the "Fill up in Homestead" rule. Gas in Key West is often 50 cents to a dollar more expensive per gallon than it is on the mainland. It adds up.
Actionable Next Steps for Your Trip
- Download Offline Maps: Cell service can be spotty in the middle of the long bridges. Download the Florida Keys map on Google Maps for offline use so you don't lose your way if the signal drops.
- Check the Drawbridge Schedule: The Snake Creek Bridge at MM 85.5 is the only remaining drawbridge on the main road. It opens on the hour for boat traffic. If you're hitting it at 1:55 PM, be prepared for a 10-minute standstill.
- Locate the "Green Marker" for Stops: If you want to break up the drive, stop at Robbie’s of Islamorada (MM 77) to feed the tarpon. It’s chaotic and touristy, but it’s a staple for a reason.
- Verify Your Parking Situation: Call your accommodation now and ask specifically, "Is there on-site parking, or is it street parking?" If it's street parking, ask for the nearest public garage address.
- Monitor the Weather: High winds can sometimes cause spray or debris on the lower bridges. If a tropical system is in the area, the Overseas Highway can become dangerous quickly due to crosswinds.