Honestly, usually when I hear “road trip,” my mind thinks hours stuck in a car, gross fast food, and “I’d rather just fly”.
BUT, there is a 113-mile stretch of highway down south that I would road trip on every year if I could!
Driving the Overseas Highway all the way down to Key West is a classic American bucket-list trip, and it’s one of the prettiest and most unique drives in the entire country. You’re literally driving over the open ocean, surrounded by turquoise waters on both sides, crossing 42 different bridges.
The biggest mistake you can make is treating this highway just like another road to drive from one end to the other without stops.
The magic is in pulling over and exploring the islands at your own pace.
If you are ready for the ultimate U.S. road trip, here are the essential stops you need to make as you hop from key to key.
1. Key Largo: The Laid-Back Dive Capital
The first time we did this road trip (which you can read about here if you like), we decided to fly into Miami, rent a Camaro, and drive to Key West in style. 10/10 recommend (100/10 if you can get a convertible!).
Key Largo is the first major stop after leaving the mainland acts as the gateway to the Keys, and it is one of the best ones, so you start your trip off on a great note!
It’s a great spot to go diving (or learn how if you’ve never tried), and it definitely lives up to the hype.
- The Underwater Scene: I spend a lot of my travel time scuba diving, from deep Caribbean walls to shallow reef dives. I was eager to get in the water here when we decided to do the trip. I was blown away by the conditions. The diving in Key Largo is some of the most laid-back I have ever done. Because the offshore reefs are so shallow, you get tons of natural sunlight illuminating the coral, and you can stay underwater much longer without worrying about aggressive depths or strong currents. It’s just EASY, and probably one of the best places in the world to learn to dive if you are a newbie.
- State Park Access: This is where you will find John Pennekamp Coral Reef State Park, the first undersea park in the country, which is definitely worth seeing whether you are diving, snorkeling, or just taking a glass-bottom boat tour.
Tip From The Editor (me): If you are diving or snorkeling in Key Largo, request a boat charter that visits the Christ of the Abyss statue. It is a nine-foot-tall bronze statue resting in about 25 feet of water. It gets crowded, so book an early morning departure to beat the main rush of day-trippers.
2. Islamorada: Craft Beer and Roadside Seafood
Islamorada is known as the Sport Fishing Capital of the World, but for us, it was the perfect place to stretch our legs and dive straight into the local food and drink scene. And you won’t be disappointed, trust me!
- The Local Pours: We made a deliberate stop at the Florida Keys Brewing Company, and it SUCH a vibe. Imagine you let an extremely skilled toddler go bananas with all the colors of the rainbow, and that is the decor that awaits when you walk in. It is the Upper Keys’ first microbrewery, featuring a colorful outdoor beer garden hidden in the back where you can kick back with a flight of locally inspired ales surrounded by tropical plants.
- Roadside Eats: We stopped for different food options constantly along this stretch. You cannot drive through Islamorada without pulling into a casual, open-air seafood shack to grab fresh conch fritters, smoked fish dip, and a massive blackened mahi-mahi sandwich. In this case, we went right across the street to Morada Bay restaurant (tasty American eats) and ate great dinner with our toes in the sand while we watched the sunset.
Tip From The Editor (me): While you are in Islamorada, take a quick detour to Robbie’s Marina. For a couple of bucks you can buy some bait and hand-feed hundred-pound tarpon right off the dock. Its a classic Keys attraction that breaks up the drive.
Note From The Editor
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3. The Middle & Lower Keys: Hidden Beaches & State Parks
This is where the Overseas Highway truly shines. As you push further south over the iconic Seven Mile Bridge, the turquoise waters seem like they stretch to infinity. We made a few stops at random points along the way to take things in. There are plenty of points where you’ll see people parked off the side to fish, and if you follow their lead you can get some pretty amazing views!
- The State Parks: There are tons of State Parks dotting the highway on the way down, and they are definitely worth the entrance fees. Most people assume the Keys are packed with massive sandy shores, but natural beaches are actually quite hidden and rare down here.
- The Best Stretch of Sand: The absolute best beach we found was inside Bahia Honda State Park. It has one of the few truly natural white-sand beaches along the highway. The water is crystal clear and offers a great view of the historic, abandoned railway bridge in the distance.
Tip From The Editor (me): Don’t just pull into Bahia Honda for a quick photo. Pack a cooler, grab a spot on Calusa Beach inside the park, and spend a few hours wading in the warm water before tackling the final stretch of the drive down to Mile Marker Zero.
4. Key West: The Grand Finale
Key West is a special place, for sure. You finally reach the end of the road, and the atmosphere completely shifts into this quirky, historic, bohemian island paradise. It’s one of the most unique places in the U.S. in my mind. And weirdly my favorite thing here has nothing to do with beaches, florida weather, or water… it’s saying hi to all the six toed kittys at the Hemingway House!
- The Culture: You trade the open ocean highway for narrow, shaded streets lined with wild roaming roosters, massive banyan trees, and beautifully restored pastel conch houses.
- The Celebration: After 113 miles of driving, nothing feels better than parking the car for good, walking down to Mallory Square, and joining the massive nightly crowd to watch the sun drop directly into the Gulf of Mexico.
Tip From The Editor (me): You don’t need a rental car once you reach Key West—in fact, parking is a massive headache. Park your car at your hotel for the weekend and rent a cruiser bike instead. The island is totally flat, and biking is hands-down the best way to navigate the historic seaport and hidden side streets.
So much more than just a drive!
The Overseas Highway is so much more than just a road to get you from point A to point B. It is a multi-day adventure suspended right over the ocean, and one that I would love the chance to do every single year. If you still haven’t scratched it off your bucket list (or added it in the first place) it is worth it!
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