Your Guide to Driving to Key West

A great road trip to Key West is all about what you do before you even get behind the wheel. A little bit of prep work turns what could be a stressful drive into the kick-off of an amazing vacation.

We're going to cover the best times to make the trip, helping you sidestep gnarly weather and packed crowds. You'll also get my best advice on picking the right rental car—and how to avoid getting dinged on insurance or tolls. Finally, I'll share a quick packing list tailored for the Keys, so you remember everything from sunblock to the right road trip snacks.

Your Essential Pre-Trip Planning

The drive from Miami down to the Southernmost Point isn't just a way to get there; it's a huge part of the experience itself. Getting the logistics sorted out ahead of time means you can actually enjoy the ride instead of worrying about the details.

A bit of planning helps you dodge common headaches, like getting stuck in weekend traffic jams, picking a car that's too small for your luggage, or having to buy something you forgot at an expensive tourist shop.

When to Make the Drive

Picking the right time of year is a game of balancing weather against crowds. The Florida Keys are beautiful year-round, but each season has its own vibe.

• Winter (December-February): This is prime time. The weather is perfect—dry, with highs in the mid-70s. But it’s also high season, so you'll be sharing the road with more people and paying top dollar for hotels.

• Spring (March-May): This is the sweet spot for many. The weather is still gorgeous, the humidity hasn't kicked in yet, and the winter crowds start to head home after Spring Break.

• Summer & Fall (June-November): Welcome to hurricane season. August and September are the riskiest months. You can score some incredible deals, but you have to be ready for sticky humidity, daily thunderstorms, and the possibility of a tropical storm changing your plans.

Here's a pro tip for driving to Key West: If you can, avoid leaving Miami on a Friday afternoon or Saturday morning. The traffic heading down the single-lane Overseas Highway can be an absolute parking lot. A weekday morning start is your best bet for a clear run.

Choosing and Renting the Right Car

Your car is more than just transportation; it’s your key to adventure on this trip. If you're renting, think about how many people and how much stuff you have. A convertible is the classic choice for a reason, but an SUV might be a lot more comfortable for a family hauling beach gear.

You can browse different car types to see what fits your group best.

When you book, look closely at the insurance coverage and ask about their toll pass program. Florida's Turnpike is full of cashless tolls, and using the rental company's pass is way cheaper than getting hit with their administrative fees later.

Flying into Miami a day or two early? It's a good idea to look into parking options near Miami Airport hotels to make your first night hassle-free.

Driving the Legendary Overseas Highway

The drive to Key West isn't just a way to get there—it is the main event. Once you leave the Florida mainland, you’re officially on the Overseas Highway, a stunning 113-mile ribbon of road that seems to float over the turquoise water. This isn't just asphalt; it's a true engineering marvel that links dozens of islands together with 42 bridges, making your drive one of the most scenic in the world.

Believe it or not, this route was once the path of the Overseas Railroad, which was tragically destroyed by the 1935 Labor Day Hurricane. The highway you'll be driving was built in its place, opening up the Keys to the world. You can actually find some fascinating details about its history in the Monroe County historical archives.

Just know this isn't your typical highway cruise. Much of the route is a single lane in each direction. You're on "island time" whether you like it or not.

How Long It Really Takes

Your GPS might optimistically tell you the drive from Miami to Key West is about three and a half hours. Let's be real—that's a best-case scenario with zero traffic. A more realistic estimate, without any stops, is closer to four or even five hours.

If you’re heading down on a Friday afternoon or a Saturday morning, expect that time to stretch even longer. Traffic can get seriously backed up around Key Largo and Islamorada, and there’s often nowhere to go. My advice? Relax. Put on a good playlist and just embrace the slower pace as part of the whole experience.

Don’t even think about trying to rush this drive. Overtaking is tricky and often dangerous. The real magic of the Overseas Highway is in the journey itself, not in shaving a few minutes off your arrival time.

Learning to Speak "Mile Marker"

The little green mile marker (MM) signs on the side of the road are your new best friend. They start at MM 113 in Florida City and count all the way down to the famous MM 0 sign in Key West. Everything in the Keys—from restaurants to dive shops—is located by its mile marker.

Learning how to use them will make your trip a breeze:

• Finding Your Stops: An address for a great lunch spot in Islamorada might just say "MM 82." Now you know exactly where to look.

• Tracking Your Progress: Watching those numbers drop is a fun way to see how much of this incredible drive you have left.

• Easy Navigation: Honestly, it’s often easier to navigate by mile marker than by a specific street address.

For a great visual overview of what’s where, check out this map review of the Florida Keys. It’s a huge help for planning.

Knowing When to Stop (and When to Keep Driving)

You’re going to be tempted by countless scenic pull-offs, quirky shops, and waterfront restaurants. While a little spontaneity is part of the fun, it helps to have a loose plan. The Seven Mile Bridge, for example, is an absolute must-see. But the best photo ops aren't from the driver's seat; they're from the old pedestrian bridge at the Marathon end or from Bahia Honda State Park just south of it.

Try to pick one or two key stops you absolutely want to make beforehand. If you pull over for every pretty view, a five-hour drive can quickly turn into a ten-hour marathon. You’ll want to save some energy—and daylight—for exploring Key West once you finally get there.

The Best Stops on Your Florida Keys Road Trip

The drive to Key West is so much more than just a route from point A to B; the journey is the main event. One of the biggest mistakes people make is blasting straight through to Duval Street without soaking in what the other islands have to offer. The real magic is found in the quirky, beautiful, and unforgettable stops dotted along the Overseas Highway.

Your road trip isn't just about the final destination. The drive itself is packed with incredible sights, and you'll want to plan for a few scenic breaks along the way. To get a better feel for your options, check out some of the top places to visit in the Florida Keys and start building your personal itinerary.

I've put together a few of my absolute can't-miss experiences that truly capture the unique spirit of the Keys.

Key Largo: Exploring the Underwater World

Your first major stop after leaving the mainland is Key Largo, and for good reason—it’s the self-proclaimed "Dive Capital of the World." This is your chance to see the only living coral barrier reef in the continental United States, and you don't even need to be scuba certified to do it.

Head straight to John Pennekamp Coral Reef State Park. It’s the perfect place to get your feet wet, literally.

• Glass-Bottom Boat Tours: If you want to stay dry, hop on the Spirit of Pennekamp. It's a fantastic, low-effort way to witness the vibrant underwater world without ever putting on a snorkel.

• Snorkeling Trips: The park runs multiple boat trips out to the shallow reef areas every day. It's an easy and incredible experience, perfect for beginners and families looking to see stunning coral and tropical fish.

My advice? Budget at least three hours for any boat tour here. Make sure you get there early, as the parking lot can fill up surprisingly fast, especially on weekends.

Islamorada: Laid-Back Vibes and Giant Fish

As you cruise south into Islamorada, the vibe shifts to a relaxed, sport-fishing town. It’s the perfect spot to grab a bite and experience some authentic Keys culture.

You have to go to Robbie's of Islamorada. It’s a classic for a reason. Where else can you hand-feed massive tarpon that swarm the docks? It’s a thrilling (and slightly nerve-wracking) experience you won't forget. After the adrenaline rush, kick back at the nearby Florida Keys Brewing Co., known for its funky beer garden and creative brews using local ingredients like key lime and hibiscus.

Don’t just feed the fish and run. Grab a drink at the Thirsty Tarpon bar right on the dock at Robbie’s. Watching other people's reactions to those giant fish is some of the best people-watching you'll find anywhere in the Keys.

Marathon: Conservation and an Iconic Bridge

Marathon, sitting right in the Middle Keys, is the heart of the island chain and a real hub for conservation. If you care at all about marine life, this is a must-stop.

The Turtle Hospital offers an inspiring and educational look into sea turtle rescue. The 90-minute guided tour lets you meet the current turtle "patients" and learn about the dangers they face from things like boat strikes and pollution. It’s a powerful reminder of our impact on this fragile ecosystem.

Just south of Marathon, you'll hit the world-famous Seven Mile Bridge. But here's a tip: the best views aren't from your car. Park at the north end and take a walk or bike ride along a restored section of the old bridge. The photo opportunities are incredible.

Before leaving the area, make time for Bahia Honda State Park. It's often said to have the most beautiful beaches in the Keys, and its sandy shores are perfect for a quick swim or a picnic lunch. The view of the old, broken railroad bridge from Calusa Beach is absolutely iconic.

To help you visualize your trip, I've mapped out these stops and a few others in a simple planner.

Florida Keys Road Trip Stop Planner

Here's a quick reference guide to help you plan your time. You can't do it all in one day, so pick what sounds best to you and save the rest for next time!

Stop	Location (Key & Mile Marker)	Recommended Visit Time	Main Attraction
John Pennekamp Park	Key Largo (MM 102.5)	3-4 Hours	Snorkeling & glass-bottom boat
Robbie's of Islamorada	Islamorada (MM 77.5)	1-2 Hours	Feeding giant tarpon
The Turtle Hospital	Marathon (MM 48.5)	1.5-2 Hours	Guided tour of the hospital
Seven Mile Bridge	Marathon (MM 47-40)	30-60 Minutes	Walk the old bridge for photos
Bahia Honda State Park	Big Pine Key (MM 37)	2-3 Hours	Beaches & historic bridge views
National Key Deer Refuge	Big Pine Key (MM 30.5)	30-60 Minutes	Spotting tiny Key deer

This planner should give you a solid starting point. Remember, the best part of a road trip is the freedom to explore, so don't be afraid to pull over whenever something catches your eye. That's the real spirit of the Keys.

Driving Safely in the Florida Keys

The drive down the Overseas Highway is one of the most stunning road trips you can take, but it demands your full attention. For much of the journey, you're on a two-lane road where speed limits change often.

You’ll be sharing the asphalt with a wild mix of people—locals heading to work, wide-eyed tourists in rental cars, massive RVs, and cyclists pedaling along the shoulder. Patience isn’t just a good idea here; it’s a requirement.

Think of defensive driving as your co-pilot for this trip. Tourists are known to slam on their brakes for a surprise photo op, and people slow down out of nowhere to read a sign. Always leave plenty of room between you and the car ahead, and keep your eyes scanning down the road for brake lights or anything that looks out of place.

Navigating Tourist Traffic and Two-Wheeled Hazards

As you roll into Key West, the driving dynamics shift completely. The historic Old Town features narrow streets packed with pedestrians, zippy electric golf carts, and a ton of scooters and mopeds. These are a huge hit with visitors, many of whom have never ridden one before.

This chaotic mix creates a very specific kind of risk. In fact, local police data showed moped and scooter crashes jumped from 338 in 2014 to 382 in 2015. It’s a real and present hazard you need to be aware of. You can dig deeper into the local traffic safety trends in the Keys Weekly if you want to see the full statistics.

To keep everyone safe, your best bet is to assume a scooter or cyclist could do something completely unpredictable at any moment.

Here are a few tips from experience for sharing the road:

• Double-Check Your Blind Spots: Seriously, look twice before you turn or change lanes. Scooters are masters of hiding just out of view of your mirrors.

• Give Them Space: When you pass a cyclist or a scooter, swing wide and give them as much room as you’d give a car. A strong gust of wind can easily push them into your lane.

• Expect Sudden Stops: Tourists on two wheels are usually looking at the sights or a map on their phone—not the road. Be ready for them to brake for no apparent reason.

Understanding Congestion and Parking Challenges

Don't assume the traffic jams are only on the main highway. A few spots are famous for backups, especially on weekends or during peak season. The stretches around Key Largo, Islamorada, and the approach to the Seven Mile Bridge can slow to an absolute crawl.

If you take away one safety tip, let it be this: never be in a hurry when driving to Key West. That laid-back "island time" vibe needs to start the second you get behind the wheel. Aggressive driving and risky passing are the quickest ways to turn a dream vacation into a nightmare.

Once you finally make it to Key West, the problem changes from driving to parking. On-street parking in Old Town is a unicorn—extremely rare and heavily regulated. Your best move is to secure a spot at your hotel or find a public garage and just leave the car.

Honestly, Key West is meant to be explored on foot, by bike, or with a ride-share. It’s not only more fun, but it’s a whole lot safer than trying to pilot a car through those tight, crowded streets.

Arriving and Getting Around Key West

You made it! That legendary drive is behind you, and the island paradise of Key West is at your feet. Before you dive headfirst into the Duval Street scene, let's talk about the car. Driving to Key West is a blast; driving in Key West is a totally different story.

The historic streets of Old Town are charmingly narrow, which also means they're packed with pedestrians, scooters, and cyclists. It can get chaotic fast, and navigating the tight quarters is more stressful than it's worth. Just to give you an idea, Monroe County saw nearly 2,000 vehicle crashes in 2024 alone. It’s a real-world reminder to be extra careful in this bustling environment. For a deeper dive into the numbers, you can review recent local traffic safety data.

To Drive or To Park? That is the Question

Here’s my best advice, honed over many trips to the island: find a place to park your car and leave it there. Seriously. Old Town Key West is incredibly compact—most of what you’ll want to see is packed into a walkable one-square-mile area.

If you try to drive from Mallory Square to the Southernmost Point, you'll spend far more time circling for a mythical parking spot than you will actually enjoying the sights. On-street parking is a unicorn, and where it does exist, it comes with strict time limits. Public lots and garages are your most reliable option if your hotel doesn't have parking.

Our Top Tip: Find a secure spot for your car—whether it’s at your hotel or a long-term public lot—and don't touch it again until you leave. Letting go of the car is the first step to truly slipping into that famous laid-back Key West vibe.

Smart Ways to Explore the Island

Once the car is parked, it's time to get around like a local. Ditching your vehicle isn't a downgrade; it's a huge upgrade to your vacation.

• Bicycles: This is the absolute best way to experience Key West. You’ll cover ground faster than walking, zip down tiny lanes you'd otherwise miss, and can park literally anywhere. Check with your hotel, as many offer bike rentals.

• Golf Carts: A super fun choice, especially for families or small groups. Zipping around in an open-air electric cart is a blast, but be warned, they can get expensive for multi-day rentals.

• Ride-Sharing & Taxis: Good old Uber and Lyft are always around. They're perfect for getting across the island or for that late-night ride back to your hotel after a few too many mojitos.

• Walking: Never underestimate the joy of just wandering. You'll stumble upon hidden gardens, quirky architecture, and funky little shops you’d completely miss from inside a car.

By embracing these options, you'll save yourself from traffic headaches and steep parking fees. Some savvy travelers even look up different car rental locations to drop off their car upon arrival and simply rent a new one for the drive back north. It's a smart strategy that lets you focus on what really matters: soaking up every last bit of sun and scenery.

Your Key West Driving Questions, Answered

As you get ready for this classic American road trip, a few questions always come up. Here are the straight-up answers to the most common things people ask before hitting the Overseas Highway.

Think of this as your final checklist before you turn the key and head south.

How Long Does the Drive Really Take?

Your GPS might tell you it's a 3.5-hour drive from Miami, but I can tell you from experience, that's almost never the case. A more realistic time for just driving, without any stops, is closer to 4.5 or even 5 hours.

Traffic can be a real wildcard, especially on weekends or during the busy season from December to May. Much of the Overseas Highway is just one lane each way, so a single fender-bender or slow R.V. can back things up for miles.

If you plan on actually enjoying the drive—stopping for photos, grabbing some Key lime pie, or dipping your toes in the water—you should budget a full 6 to 8 hours. This isn't a trip to be rushed; the slow pace is part of the charm.

Should I Drive or Fly to Key West?

This really boils down to what you value more: the journey itself or simply getting to the destination as fast as possible.

• Driving: This is for you if the road trip is a major part of the vacation. It’s an iconic drive for a reason. It's also usually cheaper, especially for families, and gives you total freedom to explore all the other Keys along the way.

• Flying: If you're on a tight schedule and want to spend every possible minute in Key West, flying directly into Key West International Airport (EYW) is the way to go. It’s much faster, but it almost always costs a lot more.

Do I Need a Car in Key West?

Honestly, no. Once you get to Key West, a car often becomes more of a burden than a benefit.

Old Town, where you’ll likely spend most of your time, is super compact and made for walking. Renting a bike or just using your own two feet is the absolute best way to explore its charming streets.

The best game plan is to drive down, park your car at your hotel or in a garage when you arrive, and then completely forget about it until you leave. Parking is notoriously difficult to find and expensive, and you’ll have a much more relaxing time without circling the block looking for a spot.

What's the Best Time of Day to Start the Drive?

To miss the worst of Miami's morning commute and the conga line of tourists heading south, an early start is your secret weapon. Try to be on the road by 7:00 or 8:00 AM.

Getting going this early gets you ahead of the big rush and gives you all day to enjoy the spectacular views and make a few spontaneous stops. I’d strongly recommend not starting your drive on a Friday afternoon or Saturday morning unless you absolutely have to—the traffic can be truly epic.

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