Turquoise Waters & Tiki Bar Sunsets
Turquoise Waters & Tiki Bar Sunsets
Homestead, FL 33034Key West, FL 33040
Trip overview
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.
Day-by-day itinerary
Day 1 — Homestead
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.
19200 SW 344th St, Homestead, FL 33034
John Pennekamp Coral Reef State Park
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.
102601 Overseas Hwy, Key Largo, FL 33037
Lazy Days Restaurant
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.
79867 Overseas Hwy, Islamorada, FL 33036
Cheeca Lodge & Spa
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.'
81801 Overseas Hwy, Islamorada, FL 33036
Day 2 — Marathon
The Turtle Hospital
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.
2396 Overseas Hwy, Marathon, FL 33050
Bahia Honda State Park
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.
36850 Overseas Hwy, Big Pine Key, FL 33043
Blue Heaven
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.
729 Thomas St, Key West, FL 33040
Opal Key Resort & Marina
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.
245 Front St, Key West, FL 33040
Day 3 — Key West
Fort Zachary Taylor Historic State Park
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.
601 Howard England Way, Key West, FL 33040
The Ernest Hemingway Home and Museum
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.
907 Whitehead St, Key West, FL 33040
Sloppy Joe's Bar
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.
201 Duval St, Key West, FL 33040
Day 4 — Key West
Key West Butterfly and Nature Conservatory
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.
1316 Duval St, Key West, FL 33040
Garbo's Grill at Hank's Hair of the Dog Saloon
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.
409 Caroline St, Key West, FL 33040
Smathers Beach
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.
2601 S Roosevelt Blvd, Key West, FL 33040
Green Parrot Bar
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.
601 Whitehead St, Key West, FL 33040
Day 5 — Key West
Southernmost Point Buoy
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.
Whitehead St & South St, Key West, FL 33040
Latitudes Restaurant
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.
245 Front St, Key West, FL 33040
Mallory Square Sunset Celebration
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.
400 Wall St, Key West, FL 33040
Experiences & guides
Bookable tours and stops worth a detour along this route.
Experiences
Guide content may not reflect current conditions. Always verify information before your trip.
Frequently asked questions
The Florida Keys Escape road trip covers about 156 mi and roughly 5h 24m of driving, comfortably spread across about 5 days.
This itinerary maps out 18 stops from Homestead, FL 33034 to Key West, FL 33040. Highlights include Robert Is Here Fruit Stand, John Pennekamp Coral Reef State Park, and Lazy Days Restaurant.
It begins in Homestead, FL 33034 and ends in Key West, FL 33040, following a mapped, road-following route the whole way.
The estimated cost is around $2,833, covering fuel, lodging, food, and activities. Your actual total varies with the season, your pace, and the choices you make along the way.
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