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Ultimate 5-Day Key West Adventure

Ultimate 5-Day Key West Adventure Itinerary

Published: 2024 Feb 28

Island Discovery and Sunset Sail

Morning
Start your Key West adventure with a delicious breakfast at Blue Heaven, known for its unique ambiance and mouthwatering dishes. After breakfast, head to Mallory Square to witness the vibrant street performers and enjoy the stunning views of the ocean. Take a stroll through the historic Key West Historic District and visit the iconic Southernmost Point of the Continental USA. Don't miss the chance to explore the beautiful Key West Butterfly and Nature Conservatory.
Afternoon
For lunch, indulge in the flavors of the Caribbean at Bien Caribbean Latino. After lunch, embark on the Key West Conch Train Tour to learn about the island's rich history and culture. Continue your exploration with a visit to the Ernest Hemingway Home and Museum, where you can admire the famous six-toed cats and learn about the life of the renowned author.
Evening
As the sun begins to set, set sail on the Key West Schooner Sunset Sail with Food & Drinks. Enjoy a relaxing cruise, savor delicious appetizers, and sip on refreshing drinks as you witness the breathtaking sunset. After the sail, treat yourself to a delightful dinner at Latitudes on Sunset Key, a waterfront restaurant offering a fine dining experience.
Bedtime
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Snorkeling and Watersports

Morning
Start your day with a hearty breakfast at Mangia Mangia Pasta Cafe, known for its authentic Italian cuisine. After breakfast, head to the marina for an exciting Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks. Spend the morning kayaking through the crystal-clear waters and enjoying the serene surroundings.
Afternoon
For lunch, visit Garbo's Grill, a popular food truck serving delicious Caribbean-inspired dishes. After lunch, continue your aquatic adventure with the Do It All Watersports With Parasailing. Experience the thrill of parasailing and engage in various watersports activities.
Evening
After an action-packed day, unwind with a relaxing dinner at Firefly Key West, known for its charming ambiance and delectable dishes. Enjoy the rest of the evening at leisure, perhaps taking a leisurely walk along the beach or exploring the vibrant nightlife of Key West.
Bedtime
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Dolphin Encounters and Sunset Cruise

Morning
Enjoy a delightful breakfast at Cafe Marquesa, a hidden gem known for its elegant setting and gourmet cuisine. After breakfast, embark on the Key West Dolphin Watching and Snorkeling Eco Cruise Tour. Spend the morning observing dolphins in their natural habitat and snorkeling in the pristine waters.
Afternoon
For lunch, head to The Flaming Buoy Filet Co., a cozy restaurant offering a unique dining experience. After lunch, take a leisurely bike ride with the Key West Guided Bicycle Tour with Key Lime Pie. Explore the charming streets of Key West and savor a delicious slice of the iconic key lime pie.
Evening
As the sun sets, embark on the Key West 2-Hour Sunset Sail with Live Music. Enjoy live music, delectable appetizers, and refreshing drinks as you cruise along the coast. After the sail, savor a delightful dinner at Nine One Five, a stylish restaurant known for its creative cuisine and extensive wine list.
Bedtime
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Historical Exploration and Nightlife

Morning
Start your day with a delicious breakfast at La Creperie French Cafe, known for its mouthwatering crepes and charming atmosphere. After breakfast, visit the Harry S. Truman Little White House, where you can learn about the history of the house and its significance. Continue your historical exploration with a visit to the Key West Lighthouse and Keeper's Quarters Museum.
Afternoon
For lunch, head to El Siboney Restaurant, a local favorite serving authentic Cuban cuisine. After lunch, take a guided tour of the Mel Fisher Maritime Museum to learn about the fascinating world of maritime archaeology.
Evening
In the evening, experience the vibrant nightlife of Key West with the Key West 2.5-Hour Duval Street Pub Crawl. Visit some of the best bars and pubs on Duval Street and enjoy a fun-filled evening. For dinner, indulge in a delicious meal at Blackfin Bistro, known for its innovative dishes and welcoming ambiance.
Bedtime
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Coral Reefs and Farewell Sunset

Morning
Enjoy a leisurely breakfast at Hogfish Bar & Grill, a casual waterfront restaurant known for its fresh seafood. After breakfast, embark on the Key West Reef Snorkel Morning Tour with Breakfast & Mimosas. Explore the vibrant coral reefs and encounter a variety of marine life.
Afternoon
For lunch, visit Banana Cafe Key West, a charming French bistro offering a delightful menu. After lunch, take a guided tour of the Key West Shipwreck Treasure Museum to learn about the maritime history of Key West.
Evening
Conclude your Key West adventure with the Key West Sunset Cruise with Buffet Dinner and Open Bar. Enjoy a delicious dinner, open bar, and live entertainment as you cruise along the coast and witness the stunning sunset. After the cruise, savor a farewell dinner at Louie's Backyard, a waterfront restaurant offering a memorable dining experience.
Bedtime
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