Driving from Key Largo to Key West along the Overseas Highway is one of those road trips where the journey really is part of the adventure. The farther you go, the more the scenery changes, with turquoise water, palm trees, little beaches, historic sites, colorful shops, and plenty of quirky stops along the way.
There are so many places you could stop that it can be hard to decide what is actually worth your time. These are some of my favorite stops along the way, from Key Largo through Islamorada and Marathon and finally into Key West.
Whether you have a full day or want to take your time over a couple of days, this Florida Keys road trip gives you plenty of opportunities to get out of the car, stretch your legs, take some pictures, and enjoy the island atmosphere.
1. Gilberts Resort (Key Largo)
A stop at Gilberts is a fun way to begin your Florida Keys adventure. Located right on the water, it has that laid-back Keys atmosphere that makes you feel like you've officially left the mainland behind.
It's a nice place to grab a drink or something to eat, enjoy the view, and take a few minutes to relax before continuing down the highway. Even if you're not staying here, it's worth stopping to take in the waterfront setting and get your road trip started at a slower pace.
Key Largo is much more than a place to pass through on your way to Key West. The island is lined with beautiful waterfront resorts, restaurants, marinas, and plenty of places to enjoy the water.
If you have extra time, consider spending a night or two here. One of the best parts of staying in the Keys is being able to slow down and enjoy the sunsets over the water instead of trying to fit everything into one long drive.
3. Harry Harris Park (Islamorada)
As you make your way into Islamorada, Harry Harris Park is a nice place to take a break from the road. The park has calm water, a small beach area, picnic tables, and plenty of room to simply sit and enjoy the scenery.
It's especially nice if you're traveling with kids and want somewhere they can get out, stretch their legs, and enjoy a little time by the water. Pack a picnic or just stop for a short break before continuing your drive.
4. Island Home Garden (Islamorada)
If you love plants and gardens, Island Home Garden is a fun little stop to add to your itinerary. Tucked away in Islamorada, this nursery is filled with tropical plants and garden inspiration.
And while you're there, don't overlook Gardenia's Bistro. It's a convenient place to grab a bite and makes this stop an easy combination of shopping, sightseeing, and lunch.
5. Rain Barrel Ship (Islamorada)
You can't take a Florida Keys road trip without stopping for at least one quirky photo opportunity, and Rain Barrel Village definitely fits the bill.
The giant lobster sculpture outside makes it hard to miss, and the colorful village has plenty of local character. It's a quick and easy stop, but sometimes those unexpected roadside attractions are the ones you remember most after a trip.
Robbie's Marina is one of the most well-known stops in the Florida Keys, and it's easy to see why. There's plenty going on here, so plan to spend a little time exploring rather than simply pulling over for a quick picture.
One of the biggest attractions is the enormous tarpon that gather around the docks. You can feed them, watch them jumping out of the water, browse the shops, and grab something to eat while enjoying the waterfront views.
It's a lively stop with plenty of that unmistakable Keys personality.
If you're ready for some time by the water, Anne's Beach is a beautiful place to slow down for a while. The shallow, calm water makes it especially inviting for wading, while the boardwalks provide an easy way to explore the shoreline.
There are also shaded areas and places to sit, making this a great stop for a picnic or a quiet break. After spending time on the highway, getting out and walking along the water feels like a perfect way to enjoy the natural beauty of the Keys.
By the time you reach Marathon, the scenery becomes even more spectacular. Sombrero Beach is a beautiful place to stop for a swim, walk along the shore, or simply enjoy the tropical surroundings.
Then there's the famous Seven Mile Bridge, one of the most recognizable sights in the Florida Keys. Driving across the bridge is an experience all by itself, with water stretching out in both directions.
Take your time through this part of the drive and keep an eye out for places where you can safely pull over and enjoy the views. This is one stretch of the Overseas Highway where you'll want your camera ready.
By the time you reach Marathon, the scenery becomes even more spectacular. Sombrero Beach is a beautiful place to stop for a swim, walk along the shore, or simply enjoy the tropical surroundings.
Then there's the famous Seven Mile Bridge, one of the most recognizable sights in the Florida Keys. Driving across the bridge is an experience all by itself, with water stretching out in both directions.
Take your time through this part of the drive and keep an eye out for places where you can safely pull over and enjoy the views. This is one stretch of the Overseas Highway where you'll want your camera ready.
10. Bahia Honda State Park
Bahia Honda State Park is one of the stops you won't want to rush through. The combination of soft sand, clear turquoise water, and swaying palm trees makes it one of the most beautiful places along the Overseas Highway.
11. Smathers Beach (Key West)
Once you arrive in Key West, Smathers Beach is a great place to get your toes in the sand and relax after the drive.
As Key West's largest public beach, there's plenty of room to spread out, take a walk, enjoy the water, or simply sit in the sun. The beach is also a popular spot for water activities, so it's a good place to spend some time before heading into the heart of Key West.
12. Fort Zachary Taylor (Key West)
For a little history mixed in with your beach time, head to Fort Zachary Taylor Historic State Park.
The Civil War-era fort gives you a chance to explore a piece of Key West history while also enjoying the beautiful beach and surrounding scenery. It's a nice change of pace from the busy streets of downtown Key West and a great place to spend part of an afternoon.
13. Key West Town / Duval Street & Landmarks
Finally, it's time to explore Key West.
Once you arrive in town, give yourself plenty of time to wander. Duval Street is filled with colorful buildings, restaurants, shops, bars, and plenty of the quirky personality that makes Key West so much fun.
Take time to explore the side streets, check out the local landmarks, and enjoy the atmosphere instead of trying to rush from one attraction to another. And, of course, no Key West visit would be complete without experiencing the famous sunset at Mallory Square.
By this point, you'll probably realize that Key West isn't just the destination at the end of the Overseas Highway. It's the perfect place to slow down and enjoy everything you've experienced along the way.
The Florida Keys Road Trip Is About the Journey
Driving from Key Largo to Key West is about much more than simply getting from one island to the next. The Overseas Highway takes you through a string of unique communities and beautiful landscapes, and every stop offers something a little different.
You might spend the morning walking along a quiet beach, stop to feed tarpon in the afternoon, cross the Seven Mile Bridge with turquoise water stretching out beside you, and end the day watching the sunset in Key West.
You don't have to see everything in one trip. In fact, I think part of the fun is leaving yourself enough time to pull over when something catches your eye.
So take your time, enjoy the scenery, stop often, and let yourself experience the Florida Keys at a slower pace. By the time you reach Key West, you'll probably find that some of your favorite memories came from the stops you made along the way—not just from the final destination.
Planning your own Florida Keys road trip? Be sure to check out my individual posts for the stops along the way, where I share more photos, tips, things to see, places to eat, and ideas for making the most of your time in the Florida Keys.
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