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Ultimate Key West Adventure: 8-Day Itinerary Itinerary
Last updated: 2024 Jun 14Arrival and Sunset Sail
Morning
Arrive in Key West and check into your hotel. Start your adventure with a delicious breakfast at Blue Heaven, known for its unique atmosphere and mouthwatering dishes. After breakfast, take a leisurely stroll through the historic Key West Historic District, admiring the charming architecture and learning about the city's rich history.
Afternoon
For lunch, head to Hogfish Bar & Grill, a local favorite known for its fresh seafood and laid-back vibe. After lunch, embark on the Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour to get an overview of the island's top attractions. Hop off at Mallory Square to experience the lively atmosphere and enjoy the stunning views of the sunset.
Evening
For dinner, make a reservation at Latitudes on Sunset Key, a waterfront restaurant offering a romantic and upscale dining experience. After dinner, set sail on the Key West Schooner Sunset Sail with Food & Drinks, where you can enjoy the breathtaking sunset while sipping on cocktails and savoring delicious hors d'oeuvres.
Bedtime
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Key West Historic District
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Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour
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Mallory Square
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Key West Schooner Sunset Sail with Food & Drinks
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Snorkeling and Island Exploration
Morning
Start your day with a hearty breakfast at Banana Cafe Key West, known for its delicious crepes and tropical ambiance. After breakfast, head out for a morning of adventure on the Key West Reef Snorkel Morning Tour with Breakfast & Mimosas. Explore the vibrant underwater world and enjoy a light breakfast and mimosas on board.
Afternoon
After your snorkeling adventure, grab a quick lunch at Garbo's Grill, a popular food truck serving up tasty and creative dishes. In the afternoon, visit the Key West Butterfly and Nature Conservatory to immerse yourself in the beauty of nature and observe hundreds of butterflies and exotic birds.
Evening
For dinner, indulge in a fine dining experience at Nine One Five, known for its innovative cuisine and stylish ambiance. After dinner, take a leisurely stroll along Duval Street, where you can explore eclectic shops, art galleries, and vibrant nightlife.
Bedtime
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Key West Reef Snorkel Morning Tour with Breakfast & Mimosas
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Key West Butterfly and Nature Conservatory
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Duval Street
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Historic Tours and Sunset Celebration
Morning
Enjoy a leisurely breakfast at Cafe Marquesa, a charming restaurant offering a sophisticated and delicious menu. After breakfast, embark on the Key West Conch Train Tour to learn about the island's history and culture. The narrated tour will take you to the city's top landmarks and attractions.
Afternoon
For lunch, head to Blackfin Bistro, a contemporary eatery known for its fresh seafood and creative dishes. After lunch, visit the Ernest Hemingway Home and Museum to explore the iconic author's former residence and see the famous six-toed cats.
Evening
Experience the world-famous Mallory Square Sunset Celebration, where you can enjoy live entertainment, local artisans, and breathtaking sunset views. For dinner, dine at Louie's Backyard, a waterfront restaurant offering a diverse menu and stunning ocean views.
Bedtime
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Key West Conch Train Tour
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Ernest Hemingway Home and Museum
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Mallory Square
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Dolphin Watching and Island Flavors
Morning
Start your day with a delicious breakfast at The Flaming Buoy Filet Co., a hidden gem known for its creative cuisine and welcoming atmosphere. After breakfast, embark on the Key West Dolphin Watching and Snorkeling Eco Cruise Tour to observe dolphins in their natural habitat and explore the beautiful waters of Key West.
Afternoon
For lunch, head to Santiago's Bodega, a popular tapas restaurant offering a wide variety of small plates and a vibrant atmosphere. After lunch, take a guided Key West Bicycle Tour with Key Lime Pie to explore the island's hidden gems and enjoy a slice of the famous Key Lime Pie.
Evening
Enjoy a casual dinner at Mangia Mangia Pasta Cafe, known for its authentic Italian cuisine and cozy ambiance. After dinner, take a relaxing Key West Windjammer Champagne Sunset Sail to enjoy the beautiful sunset and toast to another day in paradise.
Bedtime
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Key West Dolphin Watching and Snorkeling Eco Cruise Tour
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Key West Guided Bicycle Tour with Key Lime Pie
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Key West Windjammer Champagne Sunset Sail
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Beach Day and Southernmost Point
Morning
Start your day with a leisurely breakfast at La Creperie French Cafe, where you can enjoy a variety of sweet and savory crepes. After breakfast, spend the morning relaxing at Smathers Beach, one of the island's most popular beaches. Take a dip in the crystal-clear waters or simply soak up the sun.
Afternoon
For lunch, head to Azur Restaurant, a Mediterranean-inspired eatery offering fresh and flavorful dishes. After lunch, visit the Southernmost Point of the Continental USA to take a photo at the iconic landmark and enjoy the stunning ocean views.
Evening
Enjoy a casual dinner at Bien Caribbean Latino, a vibrant restaurant serving up Caribbean and Latin-inspired cuisine. After dinner, take a leisurely stroll to Mallory Square to experience the lively atmosphere and catch the nightly sunset celebration.
Bedtime
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Smathers Beach
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Southernmost Point of the Continental USA
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Mallory Square
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Cultural Exploration and Sunset Cruise
Morning
Start your day with a delicious breakfast at Firefly Key West, known for its Southern-inspired dishes and charming ambiance. After breakfast, visit the Key West Lighthouse and Keeper's Quarters Museum to learn about the island's maritime history and enjoy panoramic views from the top of the lighthouse.
Afternoon
For lunch, head to Martin's Restaurant & Lounge, a local favorite known for its classic American fare and welcoming atmosphere. After lunch, take a guided tour of the Harry S. Truman Little White House, where you can learn about the history of the house and its significance.
Evening
Enjoy a memorable dinner at El Siboney Restaurant, a family-owned restaurant serving up authentic Cuban cuisine. After dinner, set sail on the Key West Sunset Cruise with Buffet Dinner and Open Bar, where you can enjoy a delicious meal, open bar, and live entertainment as you cruise along the waters of Key West.
Bedtime
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Key West Lighthouse and Keeper's Quarters Museum
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Harry S. Truman Little White House
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Key West Sunset Dinner Cruise with Open Bar & Live Music
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Adventure and Pub Crawl
Morning
Start your day with a hearty breakfast at Pepe's Cafe and Steakhouse, a Key West institution known for its classic breakfast dishes and friendly service. After breakfast, embark on the Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks for a day of adventure and fun in the sun.
Afternoon
For lunch, enjoy a picnic-style meal provided on the sandbar excursion. After your adventure, take a break and relax at your hotel or explore the local shops and galleries in the area.
Evening
For a unique and memorable experience, join the Key West 2.5-Hour Duval Street Pub Crawl to explore the vibrant nightlife of Key West. Sample local drinks and enjoy the lively atmosphere as you visit some of the island's best bars and pubs.
Bedtime
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Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks
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Key West 2.5-Hour Duval Street Pub Crawl
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Farewell Key West
Morning
Enjoy a leisurely breakfast at Better Than Sex - A Dessert Restaurant Key West, a one-of-a-kind dessert restaurant offering decadent treats and a romantic ambiance. After breakfast, take a guided tour of the Key West Shipwreck Treasure Museum to learn about the island's maritime history and see artifacts from shipwrecks.
Afternoon
For lunch, head to The Flaming Buoy Filet Co., a hidden gem known for its creative cuisine and welcoming atmosphere. After lunch, take a leisurely stroll through the Key West Cemetery to learn about the island's unique burial traditions and see the historic gravestones.
Evening
Enjoy a farewell dinner at Mangia Mangia Pasta Cafe, where you can savor delicious Italian dishes and toast to the wonderful memories you've made in Key West. After dinner, take a relaxing Key West 2-Hour Sunset Sail with Live Music to enjoy the beautiful sunset and reflect on your amazing time in Key West.
Bedtime
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Key West Shipwreck Treasure Museum
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Key West Cemetery
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Key West 2-Hour Sunset Sail with Live Music
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