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![Ultimate 5-Day Key West Adventure with Sailing, Snorkeling, and Culinary Delights](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018d1f41-37a1-73ea-8b10-2ee38f6f8431/location978.jpg)
Ultimate 5-Day Key West Adventure with Sailing, Snorkeling, and Culinary Delights Itinerary
Last updated: 2024 Jun 14Island Welcome and Sunset Sailing
Morning
Kick off your Key West adventure with a delightful breakfast at Blue Heaven, known for its unique ambiance and delicious cuisine. After breakfast, take a leisurely stroll through the historic Key West Historic District, immersing yourself in the island's rich history and architecture.
Afternoon
For lunch, head to Hogfish Bar & Grill and savor their famous hogfish sandwich. Post-lunch, enjoy a guided bicycle tour of the island, including a stop at the iconic Southernmost Point of the Continental USA for a classic photo op.
Evening
Witness the stunning Key West sunset on a 2-hour Sunset Sail on the Schooner America 2.0, complete with live music and complimentary drinks. After the sail, indulge in a sumptuous dinner at Latitudes on Sunset Key, where you can enjoy fine dining with a view.
Bedtime
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![Visit Key West Historic District in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0f/64/93/42.jpg)
4.57Key West Historic District
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![Visit Key West Historic District in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0f/64/93/42.jpg)
Key West Historic District
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![Visit Southernmost Point of the Continental USA in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/df/d2/e8.jpg)
4.72Southernmost Point of the Continental USA
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![Visit Southernmost Point of the Continental USA in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/df/d2/e8.jpg)
Southernmost Point of the Continental USA
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![Visit Key West Schooner Sunset Sail with Food & Drinks in Key West](https://cdn.getyourguide.com/img/tour/0f7bb192050325b21c9f7cf7d29625c0f239d92f6bbceb251987543ccf81bf77.jpeg/21.jpg)
4.93Sunset Sail on the Schooner America 2.0
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![Visit Key West Schooner Sunset Sail with Food & Drinks in Key West](https://cdn.getyourguide.com/img/tour/0f7bb192050325b21c9f7cf7d29625c0f239d92f6bbceb251987543ccf81bf77.jpeg/21.jpg)
Sunset Sail on the Schooner America 2.0
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Snorkeling and Sandbar Excursion
Morning
Start your day with a delicious breakfast at Mangia Mangia Pasta Cafe, known for its fresh pasta and Italian flavors. After breakfast, gear up for an exciting Key West Dolphin Watching and Snorkeling Eco Cruise Tour. Spend the morning spotting dolphins and exploring the vibrant marine life.
Afternoon
The cruise includes a visit to a sandbar where you can enjoy a delightful lunch and drinks. After the cruise, take a relaxing Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks, soaking in the sun and the crystal-clear waters.
Evening
For dinner, experience the laid-back atmosphere and Caribbean-inspired cuisine at Bien Caribbean Latino. After dinner, take a leisurely walk through Mallory Square, where you can enjoy street performances and the lively Key West vibe.
Bedtime
Find amazing hotels in Key West.
![Visit Key West Dolphin Watching and Snorkeling Eco Cruise Tour in Key West](https://cdn.getyourguide.com/img/tour/8ae64e580d9afa7810da1d3e179bca027895c0d30e5b85f7aaaac3ee08607077.jpg/21.jpg)
4.55Key West Dolphin Watching and Snorkeling Eco Cruise Tour
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![Visit Key West Dolphin Watching and Snorkeling Eco Cruise Tour in Key West](https://cdn.getyourguide.com/img/tour/8ae64e580d9afa7810da1d3e179bca027895c0d30e5b85f7aaaac3ee08607077.jpg/21.jpg)
Key West Dolphin Watching and Snorkeling Eco Cruise Tour
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![Visit Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks in Key West](https://cdn.getyourguide.com/img/tour/885ae87156e598695aa199873847d76a0d72fcbf32cfc33d6057d81538225ba0.jpg/21.jpg)
4.84Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks
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![Visit Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks in Key West](https://cdn.getyourguide.com/img/tour/885ae87156e598695aa199873847d76a0d72fcbf32cfc33d6057d81538225ba0.jpg/21.jpg)
Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks
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![Visit Mallory Square in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/6d/da.jpg)
4.72Mallory Square
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![Visit Mallory Square in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/6d/da.jpg)
Mallory Square
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Historic Tours and Culinary Delights
Morning
Enjoy a breakfast at Cafe Marquesa, a hidden gem known for its elegant setting and delectable dishes. Post-breakfast, embark on the Key West Conch Train Tour, a classic way to explore the island's key landmarks and attractions.
Afternoon
After the train tour, visit the famous Ernest Hemingway Home and Museum to learn about the legendary writer's life. For lunch, head to La Creperie French Cafe and indulge in their savory and sweet crepes.
Evening
Cap off the day with a guided Key West Food Tasting and Cultural Walking Tour. Sample a variety of local flavors and learn about the island's culinary history. For a fine dining experience, make a reservation at Nine One Five, known for its creative cuisine and intimate setting.
Bedtime
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![Visit Key West Conch Train Tour in Key West](https://cdn.getyourguide.com/img/tour/622bcf5db4010.jpeg/21.jpg)
4.59Key West Conch Train Tour
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![Visit Key West Conch Train Tour in Key West](https://cdn.getyourguide.com/img/tour/622bcf5db4010.jpeg/21.jpg)
Key West Conch Train Tour
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![Visit Ernest Hemingway Home and Museum in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/65/64.jpg)
4.68Ernest Hemingway Home and Museum
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![Visit Ernest Hemingway Home and Museum in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/65/64.jpg)
Ernest Hemingway Home and Museum
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![Visit Key West Food Tasting and Cultural Walking Tour in Key West](https://cdn.getyourguide.com/img/tour/5d812cb3cb3b0.jpeg/21.jpg)
4.86Key West Food Tasting and Cultural Walking Tour
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![Visit Key West Food Tasting and Cultural Walking Tour in Key West](https://cdn.getyourguide.com/img/tour/5d812cb3cb3b0.jpeg/21.jpg)
Key West Food Tasting and Cultural Walking Tour
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Duval Street Pub Crawl and Sunset Party
Morning
Start your day with a hearty breakfast at The Flaming Buoy Filet Co., a top spot for seafood lovers. After breakfast, explore the vibrant Duval Street at your own pace, visiting the unique shops and galleries.
Afternoon
For lunch, head to Garbo's Grill for their famous gourmet food truck offerings. After lunch, enjoy a leisurely afternoon at Smathers Beach, one of the best spots on the island to relax and soak up the sun.
Evening
Join the fun on a 2.5-hour Duval Street Pub Crawl, experiencing the lively bar scene and enjoying drinks at multiple popular establishments. As the night progresses, hop on a Key West Sunset Party Cruise by Catamaran, complete with music, drinks, and a festive atmosphere. Dinner will be served onboard as you witness a breathtaking Key West sunset.
Bedtime
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![Visit Duval Street in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/67/13.jpg)
4.83Duval Street
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![Visit Duval Street in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/67/13.jpg)
Duval Street
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![Visit Smathers Beach in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/67/56.jpg)
4.76Smathers Beach
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![Visit Smathers Beach in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/67/56.jpg)
Smathers Beach
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![Visit Key West 2.5-Hour Duval Street Pub Crawl in Key West](https://cdn.getyourguide.com/img/tour/5e0a14e672d2c.jpeg/21.jpg)
4.64Duval Street Pub Crawl
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![Visit Key West 2.5-Hour Duval Street Pub Crawl in Key West](https://cdn.getyourguide.com/img/tour/5e0a14e672d2c.jpeg/21.jpg)
Duval Street Pub Crawl
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![Visit Key West Sunset Party Cruise by Catamaran in Key West](https://cdn.getyourguide.com/img/tour/57f3c739b06b5.jpeg/21.jpg)
4.70Key West Sunset Party Cruise by Catamaran
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![Visit Key West Sunset Party Cruise by Catamaran in Key West](https://cdn.getyourguide.com/img/tour/57f3c739b06b5.jpeg/21.jpg)
Key West Sunset Party Cruise by Catamaran
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Island Farewell and Culinary Exploration
Morning
Enjoy a delightful breakfast at Firefly Key West, known for its fresh and innovative dishes. After breakfast, take a walk through the serene Key West Butterfly and Nature Conservatory, surrounded by beautiful butterflies and tropical plants.
Afternoon
For lunch, visit Blackfin Bistro and indulge in their diverse menu with a focus on local seafood. After lunch, spend your afternoon at the Key West Shipwreck Treasure Museum, where you can learn about the island's maritime history and the era of shipwrecks.
Evening
Conclude your Key West journey with a memorable dinner at Better Than Sex - A Dessert Restaurant Key West, where you can enjoy a unique dining experience with decadent desserts. After dinner, take a leisurely walk along the Edward B. Knight Pier and reflect on your amazing time in Key West.
Bedtime
Find amazing hotels in Key West.
![Visit Key West Butterfly and Nature Conservatory in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/2c/f5/31.jpg)
4.94Key West Butterfly and Nature Conservatory
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![Visit Key West Butterfly and Nature Conservatory in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/2c/f5/31.jpg)
Key West Butterfly and Nature Conservatory
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![Visit Key West Shipwreck Treasure Museum in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/7d/be.jpg)
4.58Key West Shipwreck Treasure Museum
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![Visit Key West Shipwreck Treasure Museum in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/7d/be.jpg)
Key West Shipwreck Treasure Museum
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![Visit Edward B. Knight Pier in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/2d/13/bc.jpg)
4.77Edward B. Knight Pier
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![Visit Edward B. Knight Pier in Key West](https://media.tacdn.com/media/attractions-content--1x-1/0b/2d/13/bc.jpg)
Edward B. Knight Pier
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