Turquoise Waters & Tiki Bar Sunsets
Coastal

Turquoise Waters & Tiki Bar Sunsets

Turquoise Waters & Tiki Bar Sunsets

Homestead, FL 33034Key West, FL 33040

5 days18 stops
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5
Days
18
Stops
active
Region

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.

Trip highlights

Robert Is Here Fruit Stand
Robert Is Here Fruit Stand
Blue Heaven
Blue Heaven
Garbo's Grill at Hank's Hair of the Dog Saloon
Garbo's Grill at Hank's Hair of the Dog Saloon
Mallory Square Sunset Celebration
Mallory Square Sunset Celebration

The route

  1. 1Homestead, FL 33034Start · 25.5492, -80.5226
  2. 2Robert Is Here Fruit StandStop · 25.4474, -80.5018
  3. 3John Pennekamp Coral Reef State ParkStop · 25.1271, -80.4087
  4. 4Lazy Days RestaurantStop · 24.8983, -80.6570
  5. 5Cheeca Lodge & SpaStop · 24.9175, -80.6334
  6. 6The Turtle HospitalStop · 24.7098, -81.1014
  7. 7Bahia Honda State ParkStop · 24.6583, -81.2536
  8. 8Blue HeavenStop · 24.5517, -81.8028
  9. 9Opal Key Resort & MarinaStop · 24.5586, -81.8077
  10. 10Fort Zachary Taylor Historic State ParkStop · 24.5458, -81.8087
  11. 11The Ernest Hemingway Home and MuseumStop · 24.5512, -81.8007
  12. 12Sloppy Joe's BarStop · 24.5591, -81.8050
  13. 13Key West Butterfly and Nature ConservatoryStop · 24.5476, -81.7968
  14. 14Garbo's Grill at Hank's Hair of the Dog SaloonStop · 24.5578, -81.8055
  15. 15Smathers BeachStop · 24.5520, -81.7687
  16. 16Green Parrot BarStop · 24.5541, -81.8030
  17. 17Southernmost Point BuoyStop · 24.5469, -81.7964
  18. 18Latitudes RestaurantStop · 24.5630, -81.8143
  19. 19Mallory Square Sunset CelebrationStop · 24.5600, -81.8078
  20. 20Key West, FL 33040End · 24.5599, -81.8070

Day 2

Robert Is Here Fruit Stand
Local Experience

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.

John Pennekamp Coral Reef State Park
Outdoor Adventure

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.

Lazy Days Restaurant
Dining

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.

Cheeca Lodge & Spa
Lodging

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.'

Day 3

The Turtle Hospital
Local Experience

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.

Bahia Honda State Park
Outdoor Adventure

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.

Blue Heaven
Dining

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.

Opal Key Resort & Marina
Lodging

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.

Photo by Amaury GB

Day 4

Fort Zachary Taylor Historic State Park
Outdoor Adventure

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.

The Ernest Hemingway Home and Museum
Historical Site

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.

Sloppy Joe's Bar
Nightlife

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.

Day 5

Key West Butterfly and Nature Conservatory
Local Experience

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.

Garbo's Grill at Hank's Hair of the Dog Saloon
Dining

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.

Smathers Beach
Outdoor Adventure

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.

Green Parrot Bar
Nightlife

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.

Day 6

Southernmost Point Buoy
Scenic Viewpoint

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.

Latitudes Restaurant
Dining

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.

Mallory Square Sunset Celebration
Entertainment

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.

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Robert Is Here Fruit Stand

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.

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Florida Keys Escape