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Ultimate 5-Day Key West Adventure: Beaches, History & Nightlife Itinerary
Last updated: 2024 Jun 14Beach Day & Historic Sites
Morning
Start your day with a delicious breakfast at Blue Heaven, known for its unique ambiance and mouthwatering dishes. After breakfast, head to Smathers Beach for a relaxing morning by the ocean, soaking up the sun and enjoying the clear waters.
Afternoon
For lunch, make your way to Mangia Mangia Pasta Cafe for a delightful Italian meal. Afterward, visit the Southernmost Point of the Continental USA for a photo op and then explore the Key West Butterfly and Nature Conservatory, a serene oasis with beautiful butterflies and tropical plants.
Evening
In the evening, enjoy a sumptuous dinner at Latitudes on Sunset Key, a restaurant with stunning views. Afterward, take a leisurely stroll along Mallory Square and catch the lively sunset celebration with street performers and local artisans.
Bedtime
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4.76Smathers Beach
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4.76Smathers Beach
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4.72Southernmost Point of the Continental USA
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4.72Southernmost Point of the Continental USA
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Snorkeling & Sunset Sail
Morning
Start your day with a hearty breakfast at Cafe Marquesa. Then, embark on an exciting Key West 3-Hour Coral Reef Snorkeling adventure to explore the vibrant underwater world of the Florida Keys National Marine Sanctuary.
Afternoon
After snorkeling, enjoy a relaxing lunch at Firefly Key West. In the afternoon, take a Key West Schooner Sunset Sail with Food & Drinks for a memorable experience on the water, complete with stunning views and delicious refreshments.
Evening
For dinner, savor the flavors of the Caribbean at Bien Caribbean Latino. Afterward, unwind with a drink at Garbo's Grill, known for its laid-back atmosphere and tasty cocktails.
Bedtime
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4.23Key West 3-Hour Coral Reef Snorkeling
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4.23Key West 3-Hour Coral Reef Snorkeling
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4.75Florida Keys National Marine Sanctuary
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4.75Florida Keys National Marine Sanctuary
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Historical Exploration & Ghost Tour
Morning
Enjoy a leisurely breakfast at La Creperie French Cafe. Then, delve into the history of Key West with a visit to the Harry S. Truman Little White House and the Mel Fisher Maritime Museum.
Afternoon
For lunch, head to Blackfin Bistro for a delightful meal. In the afternoon, take a Key West Ghosts & Gravestones Guided Trolley Tour to discover the city's spooky past and haunted locations.
Evening
Enjoy a unique dining experience at Better Than Sex - A Dessert Restaurant Key West, known for its decadent desserts. Afterward, explore the vibrant nightlife of Duval Street and visit some of the iconic bars and pubs in the area.
Bedtime
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4.67Harry S. Truman Little White House
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4.67Harry S. Truman Little White House
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4.45Mel Fisher Maritime Museum
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4.45Mel Fisher Maritime Museum
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Adventure & Sunset Party Cruise
Morning
Start your day with a delicious breakfast at Nine One Five. Then, get ready for an exciting Key West Jet Ski Island Tour to explore the waters around the island and enjoy some adrenaline-pumping fun.
Afternoon
After jet skiing, have a leisurely lunch at The Flaming Buoy Filet Co.. In the afternoon, take a Key West Sunset Party Cruise by Catamaran for a festive experience on the water with music, drinks, and a beautiful sunset backdrop.
Evening
For dinner, indulge in a meal at Azur Restaurant, known for its Mediterranean-inspired cuisine. Afterward, continue the evening with a visit to Mallory Square for the nightly sunset celebration.
Bedtime
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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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4.70Key West Sunset Party Cruise by Catamaran
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4.70Key West Sunset Party Cruise by Catamaran
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Bicycle Tour, Key Lime Pie & Departure
Morning
Start your final day with a guided Key West Guided Bicycle Tour with Key Lime Pie to explore the charming streets and hidden gems of Key West. Enjoy a slice of the famous key lime pie at Blue Heaven as a mid-morning treat.
Afternoon
After the bike tour, have a farewell lunch at Hogfish Bar & Grill, a local favorite for seafood. Spend your last afternoon strolling through the Key West Historic District and visiting any sites you may have missed.
Evening
Conclude your Key West adventure with a memorable dinner at Louie's Backyard, known for its waterfront dining experience. Reflect on your incredible trip as you enjoy the evening breeze and the sounds of the ocean.
Bedtime
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4.88Key West Guided Bicycle Tour with Key Lime Pie
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4.88Key West Guided Bicycle Tour with Key Lime Pie
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4.57Key West Historic District
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4.57Key West Historic District
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