Florida Keys Road Trip: 10 Stops On The Overseas Highway

No need to deviate from the epic Overseas Highway on the way from Key Largo to Key West. The road cuts right through the island towns, offering many great pit stops along the way. We spent three days driving the Florida Keys, gaining one pound per mile.

Key Largo

Mrs. Mac’s Kitchen

No visit to the Keys would be complete without indulging in its most famous dish. It was only ten in the morning but who could resist a slice of World Famous Key Lime Pie? Mrs. Mac’s Kitchen offers a first taste of paradise upon entering the Upper Keys.

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Lazy Days

Half an hour later and we found ourselves sitting in another restaurant. Not just any restaurant however: Lazy Days’ tables are right on the beach. Add a beer and huge crab salad to that and you’re officially in paradise.

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Marathon

Sunset Grille

For the best sunset in the Keys, head to Sunset Grille in Marathon. Its outdoor patio offers front row seats to sunset over the Seven Mile Bridge. The vibe is so laid back that it attracts spring breakers from all over the country – and all ages.

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Seven Mile Bridge

The most spectacular part of the Overseas Highway is the Seven Mile Bridge, which connects the Middle Keys with the Lower Keys over a span of seven miles. Truth is we were slightly underwhelmed when driving over the bridge. It wasn’t until we saw the sunset from the water that we realized the bridge’s magnitude.

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Key West

Mile Marker Zero

The end of the Overseas Highway is marked by a much photographed sign. To our big surprise, there was a crazy long line when we first got to the marker. We opted for the beach instead and came back in the much calmer afternoon.

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Hemingway House

Ernest Hemingway had some very productive writing years while he was living in the house at 907 Whitehead Street. He was held company by more than 100 cats, half of them with six toes on each foot. Up to date, the house is inhabited by many descendants of Hemingway’s first six-toed cat.

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Fort Zachary State Park

There is not much beach in Key West, but Fort Zachary State Park has all you need for a relaxing beach day. That is if you love crystal clear waters, a beach bar with frozen mango margaritas and modest crowds.

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Mallory Square Sunset

Every night, there is a sunset celebration at Mallory Square. Half the island comes together to watch the sun set over the Gulf of Mexico, accompanied by street artists and food vendors. Prime seats and margaritas are available at Sunset Pier.

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Bar Hopping on Duval Street

Duval Street counts numerous legendary bars. The Green Parrot claims to be the oldest bar on US 1, while Sloppy Joe’s was Hemingway’s favorite watering hole. Other bars to stop by are Blue Heaven, with a heavenly rooftop terrace, and Turtle Kraals, to watch the sunset over Key West harbor. It is the home of the sunset after all.

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Key West Houses

The streets of Key West breathe summer, with beautiful town houses everywhere. Our B&B The Artist on Fleming is housed in one of those. Wander or bike the streets of Key West in search of your future vacation home, with a hydrating stop now and then.

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Bonus: Dry Tortugas Escape

While not located in the Keys, Key West does serve as the gateway to Dry Tortugas National Park. The group of islands is located 70 miles of the coast of Key West, and only accessible by ferry or seaplane. Take the ferry from Key West harbor in the morning for a tropical day trip. More on our amazing escape to Dry Tortugas can be found here.

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