Florida Keys Road Trip: 10 Essential Stops on the Overseas Highway

March 19, 2025

The Florida Keys are an archipelago off the southern Florida coast, extending into the Gulf of Mexico for 120 scenic miles. The Overseas Highway cuts through azure-blue waters to connect the Keys with the mainland. Embark on an epic Florida Keys road trip with these 10 essential stops from Key Largo to Key West.

#1- Mrs. Mac’s Kitchen, Key Largo

Mrs. Mac’s Kitchen offers a first slice of paradise upon entering the Upper Keys. The colorful restaurant is a staple in the Florida Keys, and so is their World Famous Key Lime Pie. This citrusy sweet treat is the Keys’ favorite dessert, but pairs just as well with a morning cup of coffee.

#2- Lazy Days, Islamorada

Islamorada’s Lazy Days restaurant channels island vibes like no other. With tables right on the beach, great seafood and a long menu of tropical cocktails, the tone is set for lazy days on the Keys. Walk out to the pier to feed huge tarpon fish and pelicans.

#3- Sunset Grille & Raw Bar, Marathon

There is serious sunset competition in the Florida Keys, but the Sunset Grille & Raw Bar in Marathon manages to stand out. The outdoor patio on the water offers front row seats to sunset over one of the Keys’ landmarks, the Seven Mile Bridge. On the menu are island staples like conch fritters and stone crab claws, in addition to an extensive sushi selection.

#4- Seven Mile Bridge, Marathon

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. One of the best ways to take in the bridge’s magnitude is from the Sunset Grille’s patio. Alternatively, you can walk or bike parallel with the Seven Mile Bridge on a section of the Old Seven Mile Bridge.

#5- Bahia Honda State Park, Big Pine Key

Bahia Honda State Park is named after another iconic bridge in the Keys. The Bahia Honda Rail Bridge was constructed as part of Henry Flagler’s groundbreaking Overseas Railroad, just like the Old Seven Mile Bridge. The bridge was put out of use in the seventies and is now offering stunning views to pedestrians. The state park is home to some of the best beaches in the Keys, as well as a gorgeous oceanfront campground.

#6- Hemingway Home, Key West

Ernest Hemingway lived on 907 Whitehead Street in Key West for close to a decade in the 1930s. His beautiful home was turned into a museum, open to the public daily. Back in the day, Hemingway was held company by more than 100 cats, half of them with six toes on each foot. The descendants of Hemingway’s original six-toed cat still roam the grounds up to date.

#7- Fort Zachary State Park, Key West

Beaches in Key West are limited, but Fort Zachary State Park has everything in store for a perfect beach day. Beach equipment and snorkeling gear are for rent at the state park’s idyllic beach. Follow in Hemingway’s footsteps with a daiquiri from oceanfront Cayo Hueso Café.

#8- Mallory Square Sunset Celebration, Key West

The sunset celebration at Mallory Square is quintessential Key West. Every night, the island comes together to watch the sun sink into the Gulf of Mexico, accompanied by street artists, music and food vendors. The Sunset Pier offer the best seats to Key West’s sunset spectacle, with island-proof cocktails and snacks.

#9- The streets of Key West

The colorful streets of Key West are made for wandering island-style. Go for brunch with the roosters at Rams Head Southernmost or Blue Heaven, admire beautiful summer homes, pick a happy hour deal and dine alfresco on inviting outdoor patios. Once the sun goes down, Duval Street’s legendary bars come to live. The Green Parrot claims to be the oldest bar on U.S. Route 1, while Sloppy Joe’s was Hemingway’s favorite watering hole.

#10- Southernmost Point Buoy, Key West

The start of the Overseas Highway is marked by an iconic buoy, indicating the southernmost point of continental USA. Depending on the time of day, the line for a picture can extend well around the block. Plan your visit in late afternoon for the shortest wait.

Bonus: Dry Tortugas National Park

Key West is the gateway to Dry Tortugas National Park, an island group located 70 miles west of the Keys. Dry Tortugas is only accessible by boat or seaplane, making it one of the least visited national parks. Board the Dry Tortugas Ferry from Key West Harbor in the morning for an unforgettable day trip to this remote tropical paradise.