Best Ever Drive From Fort Lauderdale to Key West — Ultimate Road Trip

October 2, 2023 Zak

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Key West makes the perfect getaway for anyone in Southeast Florida. The drive isn’t too long, there are plenty of interesting stops along the way, and the scenery is fantastic. And hopping your way down the Overseas Highway provides a great respite from the monotony of driving endless interstates everywhere you go.

Key West feels like a tropical paradise; in many ways, it is closer to the Caribbean than other parts of the US. But the islands of the Florida Keys are connected for easy travel thanks to the glorious Overseas Highway. The highway opened in the 1930s, but, believe it or not, it followed the route of the even more famous Overseas Railroad.

The railroad was the dream of Henry Flagler, the man who connected Florida to the world via rail and the mastermind behind the OG Florida resorts like The Breakers in Palm Beach and Hotel Ponce de Leon in St. Augustine (now Flagler College). Flager kept migrating south like a true snowbird, and he didn’t stop until he got to Key West.

For history buffs, the drive to Key West is a fascinating one. If you want to learn more as you drive along, check out the GuideAlong app audio tour of the Florida Keys.

Stop 1 — Miami and Homestead

There’s no reason not to begin your touring before getting to the Keys. A little early lunch break in Miami is just what the doctor ordered. For a little taste of all the influences that make Miami great, head to Versailles on Calle Ocho for a Cuban coffee.

You could hop on the Turnpike and drive to Florida City, but if you’ve got the time and the traffic isn’t too bad, a side trip down to Coconut Grove is worth the effort. This underrated bayfront community is home to many eclectic bars and restaurants.

From Coconut Grove, you can take scenic backroads that connect along the bayfront. Start on Main Highway, then connect to Ingram Highway via Douglas Road. From there, Old Cutler Road winds through old South Miami down to Homestead. Along the way, you’ll see some of Miami’s nicest areas along the Bay. It’s a nice change from the sprawl you get accustomed to along the Turdpike and Useless 1.

In Florida City, you can head straight down US 1 for the Keys or take some more detours. If you turn right on Palm Drive, one mile will take you to Robert Is Here, a Homestead staple. It’s a fruit stand with some of the most delectable smoothies and milkshakes you’ve ever tasted.

You’ve probably heard that there are two roads to get to Key West. There are two roads you can take in Florida City through the Everglades, but they connect again once you get to the Keys. If you turn left onto Card Sound Road, you can stop at the famous Alabama Jacks bar. It’s right before the Card Sound toll bridge, with a waterfront seat. It’s nothing special, but it’s an iconic Florida Keys stop and a little way off the typical tourist trail.

Stop 2 — Key Largo and Islamorada

Your first stops in the Florida Keys are Key Largo and Islamorada, the Diving Capital and Sportsfishing Capitals of the World, or so they say. Key Largo is known for its snorkeling and diving since the reefs are closer to shore, and it is the site of the first underwater park in the United States, now John Pennekamp Coral Reef State Park. It’s a great place to hop on a glass-bottom boat tour and learn more in their visitor center.

Making your way south, consider popping into the Island Grill for their original tuna nachos. The nachos are good, but the view and atmosphere are even better. If you’re feeling thirsty, the Postcard Inn’s Tiki Bar is legendary in the area.

Farther into Isla, you’ll find more dining choices and places to stay if the sun is sinking low. If you’re in the mood for a fantastic date-night quality meal, don’t miss the sunset at Morada Bay. If you’d like to hang with the tourists and devour some fried fish, check out the crazy-popular Islamorada Fish Company next to the Bass Pro Shop.

The final stop in Isla should be Robbies, a marina that lets you feed their massive tarpon. Even if you just step out of the car for a moment to watch, these massive fish are worth seeing. They’re always swimming under the docks there—I wonder why? If you opt to feed them, watch your fingers.

Leaving Lower Matecumbe Key, the scenery opens up, and the views improve. You’ll cross over more bridges and see much more of the water. Don’t hesitate to stop and take some pictures. Now you know what the “Overseas” Highway is all about!

Stop 3 —Marathon

You’re really getting there now, halfway to Key West! Marathon is the Keys’ second biggest town, with groceries, hotels, resorts, and restaurants a plenty. Top picks for your first trip include Keys Fisheries or Lazy Days South, both of which have lovely waterfront vistas.

As you near Marathon, you’ll pass the Dolphin Research Center on Grassy Key. Stop in and take the tour. You can meet some new finned friends; either swim with them during a structured program with a trainer or just tour the facility and watch the show.

The Sea Turtle Hospital is a great place to stop and take a quick tour. You’ll get an up-close look at these awesome sea creatures that are normally pretty shy in the wild. The turtle hospital works to help stranded animals and returns them to the wild when they’re all better.

Sombrero Beach in Marathon is a great place for a swim and beach day if you want to get out of the car for a few.

Leaving Marathon, you’ll drive over the famous Seven Mile Bridge. It’s, um, seven miles long. It was a major engineering feat when it opened for Flagler’s Railroad in 1912. It’s still pretty cool today, and you can see the old bridge paralleling the new one the whole way.

Stop 4 — Bahia Honda State Park

Bahia Honda is one of the few places in the Keys where you can enjoy a great beach day. The state park takes up the entire island and charges a modest entry fee. You can camp on the beach there in your tent or RV, but sites book up well in advance during the busy season.

One of the neatest things about Bahia Honda is the old railroad bridge, which you can walk up a little ways for photos. The park operates a snorkel boat that takes you to Looe Key Reef if you want to get your feet wet.

Stop 5 — Big Pine and No Name Keys

The Lower Keys are a little different than the upper. The Upper Keys are narrow, and the bayside is the Everglades National Park’s shallow and protected Florida Bay area. In the Lower Keys, the islands are wider and open to the Gulf of Mexico. Since they’re bigger, there are a few opportunities to explore.

In Big Pine Key, take a right off the highway and start looking for the adorable and highly endangered Key Deer. These little guys are about the size of large dogs and live only on a few islands around here. Unfortunately, they don’t cohabitate with cars and traffic very well, which is partly why they’re critically endangered. The entire island is part of the National Key Deer Refuge.

Head to the No Name Pub to taste backwater Florida Keys life. The Pub is a staple that’s been in business since 1936 and is far enough off the typical tourist trail to boast signs that say, “You found it!” They’re known for their pizzas.

Stop 6 — Old Town, Key West

You’ve made it to the end of the road and the end of civilization. Bar hopping, walking, or biking are the preferred modes of transportation, but once you’re here, you might just want to rent a golf cart and explore. Don’t miss the famous sights, like the cute, colorful houses, the southernmost point buoy, the Ernest Hemingway home, and famous bars like Sloopy Joes, Green Parrot, and Capt. Tony’s Saloon.

End your day at Mallory Square with everyone else on the island. Everyone heads down there for the sunset celebration. You’ll see everything from street performers to classic schooners sailing into the sunset.

Stop 7 — Casual Monday Charters, Key West

Shameless self-promotion time—you have to stop by and see me while you’re here! The best way to wrap up any trip to the Keys is by spending time on a boat. Not leaving the highway and ignoring the water activities here would be a great shame!

Casual Monday is a private boat charter in the Key West area specializing in sandbar tours, snorkeling, or sunset cruises. I take six people or less, so you get a private tour with just you and your group when you book the Casual Monday. Book your charter today, and let me know what you’d like to do and where you’d like to go. The sandbars are incredible, and the snorkeling in Key West can’t be beat.

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