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Key West, Florida

5-day Trip to Key West Itinerary

Published: 2023 Oct 24
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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 burgers and tacos. Afterward, join the Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks for a unique experience exploring the sandbars and kayaking in the crystal-clear waters.
Evening
Enjoy a sunset sailing trip with the Key West Sunset Sailing Trip with Open Bar, Food and Music. Indulge in delicious food, drinks, and live music while admiring the breathtaking sunset views.
Bedtime
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Snorkeling and Cultural Exploration

Morning
Start your day with a refreshing breakfast at Santiago's Bodega, known for its eclectic menu and vibrant atmosphere. After breakfast, embark on a Key West 3-Hour Coral Reef Snorkeling adventure to explore the vibrant underwater world of Key West.
Afternoon
For lunch, visit Bien Caribbean Latino, a cozy restaurant offering a fusion of Caribbean and Latin flavors. Afterward, take a guided tour of the Ernest Hemingway Home and Museum to learn about the famous writer's life and see the iconic six-toed cats.
Evening
Experience the lively atmosphere of Duval Street and join the Key West 2.5-Hour Duval Street Pub Crawl to discover the best bars and nightlife spots in Key West.
Bedtime
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Wildlife and History

Morning
Enjoy a delicious breakfast at Nine One Five, a trendy restaurant known for its innovative dishes. After breakfast, visit the Key West Butterfly and Nature Conservatory to admire the colorful butterflies and tropical plants.
Afternoon
For lunch, savor authentic Cuban cuisine at El Siboney Restaurant. Afterward, explore the Harry S. Truman Little White House, a historic landmark that served as a winter White House for President Truman.
Evening
Join the Key West Ghosts & Gravestones Guided Trolley Tour for a spooky and entertaining tour of Key West's haunted sites. Afterward, enjoy dinner at The Flaming Buoy Filet Co., a cozy restaurant known for its delicious seafood and steaks.
Bedtime
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Adventure and Relaxation

Morning
Start your day with a delightful breakfast at Firefly Key West, a charming restaurant offering Southern-inspired dishes. After breakfast, embark on a thrilling Key West Jet Ski Island Tour to explore the beautiful coastline and enjoy the adrenaline rush.
Afternoon
For lunch, visit La Trattoria Oceanside, a waterfront restaurant serving authentic Italian cuisine. Afterward, unwind at Smathers Beach, one of Key West's most beautiful beaches, and soak up the sun.
Evening
Indulge in a sunset cruise with the Key West Sunset Cruise with Buffet Dinner and Open Bar. Enjoy a delicious dinner buffet and drinks while watching the stunning sunset over the ocean.
Bedtime
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Marine Life and Farewell

Morning
Enjoy a delightful breakfast at Louie's Backyard, a waterfront restaurant known for its stunning views and fresh seafood. After breakfast, visit the Key West Aquarium to get up close with various marine species.
Afternoon
For lunch, experience a food tasting tour with the Key West Southernmost Food and Cultural Walking Tour. Explore the local food scene and sample delicious dishes from different cuisines.
Evening
End your trip with a Key West Sunset Party Cruise by Catamaran, where you can dance, enjoy drinks, and celebrate the beautiful sunset views of Key West.
Bedtime
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