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Ultimate 5-Day Key West Relaxation and Adventure Itinerary
Last updated: 2024 Jun 14Sunset Sailing and Island Exploration
Morning
Start your day with a delicious breakfast at the iconic Blue Heaven, known for its unique atmosphere. After breakfast, head to Mallory Square to enjoy the vibrant street performers and browse the local shops.
Afternoon
For lunch, savor the flavors of the island at Latitudes on Sunset Key, a waterfront restaurant with stunning views. Afterward, embark on a Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour to get an overview of the island's history and culture.
Evening
In the evening, experience a magical sunset on a Key West 2-Hour Sunset Sail with Live Music. Enjoy the open bar and live music as you watch the sun dip below the horizon. For dinner, indulge in a seafood feast at Azur Restaurant, known for its Mediterranean-inspired dishes.
Bedtime
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4.72Mallory Square
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4.72Mallory Square
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4.45Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour
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4.45Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour
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Water Adventures and Marine Life
Morning
Enjoy a leisurely breakfast at Cafe Marquesa, a charming spot with a focus on local ingredients. After breakfast, head to the Key West Aquarium to explore the marine life of the Florida Keys.
Afternoon
For lunch, try the fresh seafood at Hogfish Bar & Grill, a local favorite. In the afternoon, set out on a Key West Dolphin Watching and Snorkeling Sunset Cruise to see dolphins in their natural habitat and snorkel in the crystal-clear waters.
Evening
End your day with a sunset dinner at Louie's Backyard, a waterfront restaurant with a laid-back atmosphere. After dinner, take a stroll down Duval Street and experience the vibrant nightlife of Key West.
Bedtime
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4.31Key West Aquarium
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4.31Key West Aquarium
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4.33Key West Dolphin Watching and Snorkeling Sunset Cruise
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4.33Key West Dolphin Watching and Snorkeling Sunset Cruise
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Historic Sites and Cultural Immersion
Morning
Start your day with a hearty breakfast at Blackfin Bistro, known for its creative cuisine. After breakfast, visit the Hemingway Home and Museum to learn about the famous writer's time in Key West.
Afternoon
For lunch, enjoy the Cuban flavors at El Siboney Restaurant, a local institution. In the afternoon, take a guided tour of the Truman Little White House, the former winter residence of President Harry S. Truman.
Evening
Relax and unwind with a spa treatment at your hotel or one of the local spas. For dinner, experience the unique dining concept at Better Than Sex - A Dessert Restaurant Key West, where every dish is a sweet delight.
Bedtime
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4.68Hemingway Home and Museum
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4.68Hemingway Home and Museum
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4.67Truman Little White House
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4.67Truman Little White House
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Outdoor Adventures and Beach Relaxation
Morning
Enjoy a leisurely breakfast at Nine One Five, a hidden gem in the heart of Key West. After breakfast, spend the morning at Smathers Beach, where you can relax on the sandy shores or try your hand at water sports.
Afternoon
For lunch, head to Garbo's Grill for some gourmet street food. In the afternoon, embark on a Key West Jet Ski Island Tour for an adrenaline-pumping adventure around the island.
Evening
Watch the sunset from the water on a Key West Schooner Sunset Sail with Food & Drinks. Enjoy a delicious dinner at Firefly Key West, known for its Southern cuisine with a modern twist.
Bedtime
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4.76Smathers Beach
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4.76Smathers Beach
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4.68Key West Jet Ski Island Tour
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4.68Key West Jet Ski Island Tour
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Relaxation and Departure
Morning
On your last day, enjoy a leisurely breakfast at The Flaming Buoy Filet Co., a cozy restaurant with a focus on fresh seafood. Spend the morning exploring the Key West Butterfly and Nature Conservatory and the Key West Lighthouse and Keeper's Quarters Museum.
Afternoon
For lunch, savor the flavors of the Caribbean at Bien Caribbean Latino. After lunch, take a final stroll through the Key West Historic District and pick up any last-minute souvenirs.
Evening
Conclude your trip with a sunset cocktail at Santiago's Bodega, a popular spot for tapas and drinks. Transfer to the airport for your departure, relaxed and rejuvenated from your time in Key West.
Bedtime
Find amazing hotels in Key West.
4.94Key West Butterfly and Nature Conservatory
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4.94Key West Butterfly and Nature Conservatory
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4.74Key West Lighthouse and Keeper's Quarters Museum
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4.74Key West Lighthouse and Keeper's Quarters Museum
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