Robert Is Here Fruit Stand
The perfect first stop leaving the Miami metro area for the Keys. Grab a famous, fresh tropical fruit milkshake (like key lime passion fruit) and stock up on exotic fruits for the drive south.
Turquoise Waters & Tiki Bar Sunsets
Homestead, FL 33034Key West, FL 33040
Homestead, FL 33034Key West, FL 33040
Embark on the ultimate tropical road trip, cruising down the legendary Overseas Highway from Miami to America's Caribbean. This journey is a sun-drenched adventure across turquoise waters, featuring island-hopping, fresh seafood, and the vibrant, laid-back culture of the Florida Keys, culminating in a spectacular Key West sunset.
The perfect first stop leaving the Miami metro area for the Keys. Grab a famous, fresh tropical fruit milkshake (like key lime passion fruit) and stock up on exotic fruits for the drive south.
Discover the underwater world at the first undersea park in the U.S. Take a glass-bottom boat tour to see the coral reefs and the iconic Christ of the Deep statue without getting wet, or rent a kayak to explore the mangrove trails.
Enjoy an incredible oceanfront dinner with your feet in the sand. Famous for its fresh, locally caught seafood, especially the Lazy Days style fish prepared with breadcrumbs, scallions, and parmesan.
A classic Florida Keys resort offering upscale rooms, a private beach, a 525-foot fishing pier, and multiple pools. It's a luxurious home base for your first night in the 'Sportfishing Capital of the World.'
Take a guided educational tour of this working hospital for injured sea turtles. You'll get to see the rehabilitation process up close and 'meet' the permanent residents who couldn't be returned to the wild.
Home to what are consistently rated the best beaches in the Florida Keys. Relax on the white sand of Calusa Beach, take in the iconic view of the old disused bridge, and swim in the clear, shallow water.
A quintessential Key West dining experience in a lush outdoor courtyard where chickens and cats roam free. Famous for its Caribbean-inspired cuisine, towering Key Lime pie, and live music.

Perfectly located waterfront resort at the heart of the action, steps from Mallory Square and Duval Street. Offers beautiful rooms, a vibrant pool area, and stunning sunset views over the marina.
Photo by Amaury GB
Arguably the best beach in Key West, this spot offers a mix of sand and coral rock, making it great for snorkeling right from the shore. Explore the historic fort before finding a shady spot under the pines to relax.
Tour the beautiful Spanish Colonial home where the famous author lived and wrote in the 1930s. Learn about his life in Key West and meet the famous six-toed cats, descendants of Hemingway's own pet.
An iconic Key West institution and a favorite haunt of Ernest Hemingway himself. It's a must-visit for its lively atmosphere, live music all day and night, and classic bar energy.
Walk through a magical glass-enclosed habitat filled with hundreds of live butterflies from around the world, colorful birds, and lush tropical plants. It's a peaceful and beautiful escape from the bustle of Duval Street.
A legendary food truck tucked inside a funky outdoor bar. Serve's up some of the best food on the island, with creative and delicious Korean BBQ tacos, burritos, and burgers that have a massive local following.
The largest public beach in Key West. It's the perfect spot for a long walk, sunbathing, or renting a paddleboard or kayak to enjoy the calm, shallow waters of the Atlantic.
A legendary dive bar that's a true local's favorite, known for its eclectic character, killer live music, and 'No Sniveling' motto. It's the antithesis of the tourist traps, offering an authentic slice of old Key West.
Snap the obligatory photo at the iconic anchored concrete buoy marking the southernmost point in the continental United States. It's a classic Key West landmark, just 90 miles from Cuba.
Take a short ferry ride to Sunset Key for an upscale beachfront dining experience. Perfect for a final farewell brunch or lunch with your toes in the sand and breathtaking views of the turquoise water.
The grand finale to your trip. Join the nightly festival of street performers, musicians, and food vendors as you watch the sun dip spectacularly into the Gulf of Mexico. It's a cherished Key West tradition that can't be missed.
Take this route with you — navigation, live weather, and gas tracking inside Road Trip.