Overseas Highway
Miami to Key West
Miami, FLKey West, FL
Trip overview
Embark on a sun-drenched journey down the legendary Overseas Highway, island-hopping from the vibrant nightlife of Miami to the laid-back paradise of Key West. This leisurely 6-day trip is filled with stunning beaches, iconic scenic drives, and unforgettable nights celebrating the unique culture of the Florida Keys.
Day-by-day itinerary
Day 1 — Miami Beach
South Beach
Kick off your trip on one of the world's most famous beaches. Soak up the sun on the white sands, admire the iconic Art Deco architecture along Ocean Drive, and dive into the vibrant atmosphere that defines Miami.
Ocean Drive, Miami Beach, FL 33139
The Clevelander South Beach
Experience the quintessential South Beach party scene at this iconic hotel's outdoor pool and patio. Known for its lively DJs, dancers, and tropical cocktails, it's the perfect place to start the nightlife portion of your adventure.
1020 Ocean Dr, Miami Beach, FL 33139
Mango's Tropical Cafe
A legendary Ocean Drive institution, Mango's offers non-stop entertainment with live bands, salsa dancing, and vibrant performances. It's a colorful, high-energy immersion into Miami's Latin-inspired nightlife.
900 Ocean Dr, Miami Beach, FL 33139
The Goodtime Hotel
Stay at this highly stylized, Art Deco-inspired hotel from Pharrell Williams and David Grutman. Its whimsical design and lively pool scene at 'Strawberry Moon' provide a perfectly immersive South Beach lodging experience.
601 Washington Ave, Miami Beach, FL 33139
Day 2 — Key Largo
John Pennekamp Coral Reef State Park
Discover the incredible underwater world of the Florida Keys at the first undersea park in the U.S. Take a glass-bottom boat tour to see the coral reefs, rent a kayak to explore mangrove trails, or snorkel around the famous Christ of the Abyss statue.
102601 Overseas Hwy, Key Largo, FL 33037
Robbie's of Islamorada
A must-do stop in the Keys for a unique local experience: hand-feeding massive wild tarpon from the dock. It's a thrilling and unforgettable encounter with marine wildlife.
77522 Overseas Hwy, Islamorada, FL 33036
Florida Keys Brewing Co
Unwind in a vibrant, artsy beer garden at this local brewery. Sample a flight of tropical-inspired craft beers, play some bar games, and enjoy the laid-back island atmosphere.
81611 Old Hwy, Islamorada, FL 33036
Cheeca Lodge & Spa
Check into this upscale beachfront resort known for its lush grounds, beautiful private beach, and classic Keys elegance. It’s the perfect luxurious base for exploring the middle Keys.
81801 Overseas Hwy, Islamorada, FL 33036
Day 3 — Islamorada
Anne's Beach
Stroll along a scenic boardwalk that winds through mangroves to various secluded beach spots. This shallow, calm water beach is perfect for wading, relaxing, and enjoying picturesque views of the Atlantic.
73500 Overseas Hwy, Islamorada, FL 33036
Sombrero Beach
A beautiful, deep sandy beach that's a favorite among locals in Marathon. It's an ideal spot for swimming in the clear turquoise water and a key nesting ground for loggerhead turtles between April and October.
Sombrero Beach Rd, Marathon, FL 33050
Sunset Grille & Raw Bar
Located at the foot of the Seven Mile Bridge, this spot offers spectacular sunset views. Enjoy sushi, seafood, and tropical drinks from their poolside bar as you watch the sun dip below the horizon.
7 Knights Key Blvd, Marathon, FL 33050
Day 4 — Marathon
Seven Mile Bridge
Drive across the most famous section of the Overseas Highway, an iconic bridge offering breathtaking panoramic views of the turquoise water. Pull over at the designated pedestrian section on the old bridge for incredible photo opportunities.
Overseas Highway (US-1), Marathon, FL 33050
Bahia Honda State Park
Home to what many consider the best natural beaches in the Florida Keys. Walk the trail to the old Bahia Honda Bridge for a stunning elevated view of the entire island and its surrounding clear waters.
36850 Overseas Hwy, Big Pine Key, FL 33043
Sloppy Joe's Bar
Dive into Key West's legendary nightlife at this historic bar, a favorite haunt of Ernest Hemingway. Known for its strong drinks, live music all day long, and a boisterous, fun-loving crowd.
201 Duval St, Key West, FL 33040
Ocean Key Resort & Spa
Settle into your Key West home at this luxurious resort located at the very end of Duval Street, overlooking the Gulf of Mexico. Its prime location offers easy access to Mallory Square and the island's best nightlife.
0 Duval St, Key West, FL 33040
Day 5 — Key West
Fort Zachary Taylor Historic State Park
Explore a Civil War-era fort and then relax on Key West's best beach, known for its clear water and excellent snorkeling just offshore. It's a perfect blend of history and natural beauty.
601 Howard England Way, Key West, FL 33040
The Green Parrot Bar
An iconic Key West dive bar that's a true local institution. Famous for its 'no sniveling' policy, incredible live music, and laid-back, anything-goes vibe. It's an essential stop for an authentic nightlife experience.
601 Whitehead St, Key West, FL 33040
Sunset Celebration at Mallory Square
Join the nightly festival at Mallory Square Dock to watch the spectacular sunset over the Gulf of Mexico. The celebration features street performers, musicians, and food vendors, creating an unforgettable Key West tradition.
400 Wall St, Key West, FL 33040
Day 6 — Key West
Smathers Beach
Spend your final morning relaxing on the largest public beach in Key West. Its long stretch of soft sand and calm, shallow waters make it a great spot for sunbathing, swimming, and people-watching.
2601 S Roosevelt Blvd, Key West, FL 33040
Southernmost Point of the Continental U.S.A.
Snap an obligatory photo at the iconic anchored buoy marking the southernmost point in the continental United States, just 90 miles from Cuba. It's a classic Key West landmark and a perfect final stop.
Whitehead St & South Street, Key West, FL 33040
Blue Heaven
Enjoy a final, iconic Key West meal in a whimsical outdoor courtyard where chickens and cats roam freely. Famous for its Caribbean-inspired cuisine, brunch, and heavenly Key Lime Pie with a mountain of meringue.
729 Thomas 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 Overseas Highway road trip covers about 199 mi and roughly 6h 54m of driving, comfortably spread across about 6 days.
This itinerary maps out 21 stops from Miami, FL to Key West, FL. Highlights include South Beach, The Clevelander South Beach, and Mango's Tropical Cafe.
It begins in Miami, FL and ends in Key West, FL, following a mapped, road-following route the whole way.
The estimated cost is around $2,849, 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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