Miami to Key West Road Trip: 9 Great Stops on the Overseas Highway

Looking for the ultimate land-meets-sea adventure? Jump in the car for a Florida Keys road trip down the Overseas Highway. The 120-mile road runs from the Florida mainland down to Key West.

Take the iconic Overseas Highway and travel from Miami to Key West.

There’s one main road into and out of Key West, and that’s the Overseas Highway. The 100-plus-miles stretch features plenty of great stops for any Miami to Key West drive, but you have to know where to look.

Here are nine activities worth checking out along the four-hour drive:

Shake Things Up at the Robert is Here Fruit Stand in Homestead

Stock up on tropical snacks at the Robert is Here fruit stand.

Before you even leave the mainland, you’ll want to fuel up at Robert is Here in Homestead. The beloved fruit stand sells tropical fare like papayas, watermelons and mangoes, all of which are great snacks for your Miami to Key West road trip. Locals know this place also is home to the best shakes in town — pick a fruit or two and have them turned into a delicious beverage. You won’t regret it.

Choice Hotels near Homestead, FL: 5

Get Up-close With Aquatic Life at John Pennekamp Park in Key Largo

Try to spy a sea turtle at John Pennekamp Park in Key Largo.

A must-do on any Miami to Key West road trip, John Pennekamp Park in Key Largo offers a variety of aquatic activities to help you stay cool in the Florida sun, such as kayaking, snorkeling and scuba diving. Those who prefer to stay dry should take advantage of the famous glass-bottom boat tours, which offer an up-close look at shallow reefs filled with wildlife.

Choice Hotels near Key Largo, FL: 1

Find Unique Arts and Crafts at Rain Barrel Artisan Village in Islamorada

Grab a selfie with Betsy, the larger-than-life lobster that greets visitors to the Rain Barrel Artisan Village.

Islamorada’s The Rain Barrel Artisan Village is hard to miss — you’ll know you’re there when you see the giant lobster sculpture on the side of the road. Once you’ve gotten your photos with the giant crustacean (affectionately named “Betsy”), pop into the actual village and enjoy the crafts and other wares from local vendors. You can find everything from jewelry and ceramics to photographs and paintings for sale. If you’re lucky, you might even spot one of the artists hard at work.

Choice Hotels near Islamorada, FL: 2

Refuel With Turtle Chowder at the Green Turtle Inn

A favorite of locals and visiting celebrities alike, the Green Turtle Inn is a favorite for authentic Keys cooking.

If you get hungry during your Miami to Key West road trip, look for the neon sign of the famous Green Turtle Inn. Since opening in 1947, the restaurant has served iconic Keys dishes to locals and celebrities alike—from Joe Namath to Jack Parr to John Belushi. Be sure to sample their signature dish, a bowl of turtle chowder (which is made from snapping turtle today, instead of the original green sea turtle).

Choice Hotels near Islamorada, FL: 2

Feed the Tarpon at Robbie’s of Islamorada

Turn yourself into a fishing lure and hand feed the tarpon at Robbie’s of Islamorada.

At Robbie’s of Islamorada, there’s no shortage of things to do. You can parasail, take a sunset cruise or go offshore fishing. But what Robbie’s is especially known for is its tarpon feeding. Adventurous visitors can brave the docks and lay low to feed the famous fish, which jumps out of the water suddenly to catch its meal. The mini heart-attack is worth the photo op.

Choice Hotels near Islamorada, FL: 2

Drive Over Seven Mile Bridge

The newer portion of the Seven Mile Bridge is for traffic, while the older portion is for pedestrians and cyclists.

Unlike the other possible stops on the miles from Miami to Key West, you have no choice but to experience this historic bridge — you literally have to drive over it to get to Key West. The longest bridge in the Florida Keys, Seven Mile Bridge is technically two bridges; the original was a railroad bridge that was eventually redone to allow for car traffic (the one you drive over today). You can still see the old bridge if you pull over — and you definitely should. Take in the breathtaking view of the waters and strike a pose for the camera.

Choice Hotels in Marathon, FL: 1

Take in a Show and More at the Dolphin Research Center in Marathon

Get up close and personal with an adorable swimming buddy at the Dolphin Research Center.

Have you ever wanted to swim with dolphins? Book a hotel in Marathon and visit the Dolphin Research Center in Marathon to check it off your bucket list. Whether you’re on your own or with family and friends on this Miami to Key West road trip, just about anyone will enjoy some time in the water with these amazing mammals. You can even paint with them here! Or, take part in a theater session, research activities and more.

Choice Hotels in Marathon, FL: 1

Hang With Sea Turtles at the Turtle Hospital in Marathon

Help a sea turtle get back on its feet—err, flippers—at the Turtle Hospital.

Since 1986, the Turtle Hospital in Marathon has been helping to rescue and rehabilitate injured sea turtles. Here, you can take a guided educational tour of the facility that gives you a chance to meet its residents. You may even consider “adopting” one of the turtles; a $35 contribution provides a turtle with food and medicine (plus, you’ll get a cute adoption certificate).

Choice Hotels in Marathon, FL: 1

Relive History at Ernest Hemingway Home and Museum in Key West

Walk where the great writer, Ernest Hemingway, once walked—and his cats’ descendants still do.

No Miami to Key West road trip is complete without a trip to the Ernest Hemingway Home and Museum. For more than a decade, the renowned author wrote on these famous grounds, which continue to be home to his iconic cats. Over 40 cats roam the property, and more than half of them have six toes; have fun identifying them throughout your individual or guided tour. Don’t forget to swing by the pool — a feature that cost the homeowner $20,000 back in 1938.

Choice Hotels near Key West, FL: 1


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