Curator’s statement
I have a deep and abiding love for the Florida Keys, a sentiment that blossomed during my many childhood visits as a Florida native. The Keys have always felt like a magical escape, where the turquoise waters, vibrant coral reefs, and swaying palm trees create a paradise unlike any other. The laid-back lifestyle and rich, colorful history captivated my young imagination, and the countless hours spent snorkeling, fishing, and exploring the unique island chain left an indelible mark on my heart. Each trip was a new adventure, filled with the warmth of the sun and the salty sea breeze, fostering a connection that continues to draw me back to this day.
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Day 1: Settling In
Welcome to your long weekend in the Florida Keys! Check into your chosen resort and take some time to relax and freshen up. For dinner, head to Sunset Grille and Raw Bar in Marathon, where you can enjoy a delicious meal while watching the sun set over the water, providing a perfect end to your first day in the Florida Keys. After dinner, if you’re in the mood for some nightlife, head back to Key West and visit Sloppy Joe’s Bar or The Green Parrot Bar for live music and a taste of the local scene.
Day 2: Exploring the Water and Sunset Sights
Begin your journey in Key West with a hearty breakfast at Blue Heaven, known for its laid-back vibe and delicious pancakes. After breakfast, take a stroll along Duval Street, exploring its eclectic mix of shops, art galleries, and historic sites. Don't miss a visit to the Ernest Hemingway Home and Museum to delve into the life of the legendary author. Next, head to the Southernmost Point Buoy for a classic photo op at this iconic landmark. Spend a serene morning at the Key West Butterfly and Nature Conservatory, surrounded by vibrant butterflies and exotic birds. For lunch, make your way to Hogfish Bar and Grill on Stock Island to enjoy fresh seafood with a waterfront view. In the afternoon, drive to Bahia Honda State Park on Big Pine Key for some relaxation and adventure. Swim, snorkel, or explore the nature trails in this pristine park. For dinner, dine like a local and visit The Flaming Buoy Filet Company.
Day 3: Exploring the Lower Keys and Enjoying Key West
Start today with breakfast at your resort, then head to Marathon to visit the Dolphin Research Center. Spend the morning interacting with dolphins and learning about marine conservation. Continue your adventure with a visit to the Turtle Hospital, where you can take a guided tour and see the rehabilitation work being done for injured sea turtles. For lunch, enjoy a meal at Island Fish Company, a waterfront restaurant known for its fresh seafood and relaxed atmosphere. In the afternoon, head to Sombrero Beach, one of the best beaches in the Middle Keys, for swimming and sunbathing. Later, explore Crane Point Hammock and Nature Trail, where you can hike through native tropical hardwood hammocks and visit the small museum and historic sites. Return to your resort to freshen up, then have dinner at Barracuda Grill, a local favorite offering a diverse menu and cozy atmosphere.
Day 4: Discovering Hidden Gems and Scenic Farewells
Begin your final day with a leisurely breakfast at a local café, then drive to the Lower Keys for a day of natural beauty and tranquility. Start with a visit to the National Key Deer Refuge on Big Pine Key, where you can spot the endangered Key deer and explore the scenic nature trails. For lunch, head to No Name Pub, a quirky, off-the-beaten-path eatery known for its pizza and unique decor. In the afternoon, visit Bahia Honda State Park again for more beach time, snorkeling, or simply enjoying the park’s breathtaking scenery. As your long weekend in the Florida Keys comes to an end, make your way back towards Miami, taking in the scenic views along the Overseas Highway one last time.
Travel Advisor
Shasta Reeves
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This itinerary is part of our ongoing series on travel to Key West.
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