Overseas Highway

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Photo by Amaury GB

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.

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.

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.

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.

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.

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.