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Key West, Florida

Ultimate Key West Adventure Itinerary

Published: 2023 Oct 23
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Exploring Key West

Morning
Start your day with a delicious breakfast at Blue Heaven, known for its Caribbean-inspired cuisine and vibrant atmosphere. After breakfast, embark on the Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour to get an overview of the city's main attractions.
Afternoon
For lunch, head to Garbo's Grill, a popular food truck serving mouthwatering gourmet burgers and tacos. Afterward, take a Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks to experience the stunning turquoise waters and enjoy kayaking in the Key West sandbar.
Evening
Enjoy a relaxing sunset sailing trip with the Key West Sunset Sailing Trip with Open Bar, Food and Music. Indulge in delicious food, sip on refreshing drinks, and listen to live music as you witness the breathtaking Key West sunset.
Bedtime
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Underwater Adventures

Morning
Start your day with a coral reef snorkeling adventure. Join the Key West 3-Hour Coral Reef Snorkeling tour, which includes all necessary equipment and offers a chance to explore the vibrant marine life of the Florida Keys. After snorkeling, enjoy a delicious breakfast and mimosas on the Key West Reef Snorkel Morning Tour with Breakfast & Mimosas.
Afternoon
Head to Nine One Five for a delightful lunch. This restaurant offers a fusion of American and Mediterranean flavors in a charming setting. Afterward, embark on a Key West Dolphin Watching and Snorkeling Eco Cruise Tour to spot dolphins in their natural habitat and snorkel in the crystal-clear waters.
Evening
For dinner, experience the culinary delights of Key West at Firefly Key West. This restaurant offers a unique blend of Southern and Caribbean flavors. After dinner, take a leisurely stroll along Duval Street and explore the vibrant nightlife of Key West.
Bedtime
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Historical Key West

Morning
Start your day by visiting the Ernest Hemingway Home and Museum, where you can explore the former residence of the famous writer and admire the beautiful gardens. Afterward, enjoy a guided tour of the Key West Conch Train Tour, which takes you through the historic district and provides fascinating insights into Key West's history.
Afternoon
For lunch, savor authentic Cuban cuisine at El Siboney Restaurant. Indulge in flavorful dishes like ropa vieja and Cuban sandwiches. After lunch, visit the Key West Shipwreck Treasure Museum to learn about the maritime history of Key West and see artifacts from shipwrecks.
Evening
Enjoy a sunset cruise with a buffet dinner and open bar on the Key West Sunset Cruise with Buffet Dinner and Open Bar. Relax, dine, and dance as you take in the breathtaking views of the sunset over the Gulf of Mexico.
Bedtime
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Outdoor Adventures

Morning
Start your day with a thrilling Key West Jet Ski Island Tour. Explore the waters surrounding Key West on a jet ski and enjoy the adrenaline rush. Afterward, grab a quick snack at Bien Caribbean Latino, known for its delicious empanadas and tropical flavors.
Afternoon
Head to Fort Zachary Taylor, a beautiful state park with a sandy beach and historic fort. Spend the afternoon swimming, sunbathing, and exploring the fort's history. For a late lunch, visit Santiago's Bodega, a tapas-style restaurant offering a variety of small plates and refreshing cocktails.
Evening
Experience the vibrant atmosphere of Mallory Square, known for its nightly Sunset Celebration. Enjoy street performers, local artisans, and stunning sunset views. For dinner, dine at Louie's Backyard, a waterfront restaurant known for its fresh seafood and stunning ocean views.
Bedtime
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Cultural Delights

Morning
Start your day with a guided bicycle tour of Key West, including a stop at La Trattoria Oceanside for a slice of their famous Key lime pie. Explore the charming streets and learn about the island's culture and history.
Afternoon
For lunch, join the Key West Southernmost Food and Cultural Walking Tour, where you can taste a variety of local dishes and learn about Key West's culinary scene. Afterward, visit the Key West Aquarium to discover the diverse marine life of the Florida Keys.
Evening
Enjoy a sunset party cruise by catamaran with the Key West Sunset Party Cruise by Catamaran. Dance, mingle, and enjoy the lively atmosphere while sipping on tropical cocktails and watching the sunset over the water.
Bedtime
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Nature and Relaxation

Morning
Spend the morning exploring the beautiful Dry Tortugas National Park. Take a ferry or seaplane to this remote island paradise and enjoy snorkeling, birdwatching, and exploring the historic Fort Jefferson. Pack a picnic lunch to enjoy in this pristine natural setting.
Afternoon
Return to Key West and relax at Smathers Beach, one of the island's most popular beaches. Soak up the sun, swim in the clear waters, or simply unwind on the sandy shore. For a late afternoon snack, visit The Flaming Buoy Filet Co., a cozy restaurant known for its creative small plates and craft cocktails.
Evening
Indulge in a seafood dinner at Louie's Backyard, where you can enjoy fresh seafood dishes while overlooking the ocean. After dinner, visit the Mallory Square for the famous Sunset Celebration, where you can watch street performers, browse local vendors, and bid farewell to Key West in style.
Bedtime
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