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Ultimate 5-Day Key West Adventure

Ultimate 5-Day Key West Adventure Itinerary

Published: 2024 Mar 01

Discovering Key West's Charm

Morning
Start your Key West adventure with a delicious breakfast at the iconic Blue Heaven. Afterward, embark on the Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour to get an overview of the island's main attractions. Hop off at Mallory Square to witness the vibrant street performers and enjoy the stunning views of the Gulf of Mexico.
Afternoon
For lunch, head to Latitudes on Sunset Key for a delightful meal on the waterfront. Afterward, take a guided tour of the Ernest Hemingway Home and Museum, where you can learn about the famous author's life and see the descendants of his beloved six-toed cats.
Evening
As the sun begins to set, board the Key West Schooner Sunset Sail with Food & Drinks for a magical experience. Enjoy a selection of hors d'oeuvres and drinks as you sail along the coast, witnessing the breathtaking sunset. End your evening with a sumptuous dinner at Firefly Key West.
Bedtime
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Snorkeling and Island Exploration

Morning
Fuel up with a hearty breakfast at Banana Cafe Key West before embarking on the Key West Reef Snorkel Morning Tour with Breakfast & Mimosas. Explore the vibrant underwater world of the Florida Keys and enjoy a delicious breakfast and mimosas on board.
Afternoon
After the snorkeling tour, grab a quick lunch at Garbo's Grill, known for its gourmet food truck offerings. Spend the afternoon at Fort Zachary Taylor, where you can relax on the beach, explore the historic fort, and take a nature walk.
Evening
In the evening, experience the lively atmosphere of Duval Street. Enjoy a diverse range of dining options and vibrant nightlife. For dinner, head to Nine One Five, a local favorite known for its contemporary cuisine. Afterward, take a leisurely stroll along the bustling street.
Bedtime
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Historical and Cultural Immersion

Morning
Start your day with a delightful breakfast at Mangia Mangia Pasta Cafe. Then, embark on the Key West Conch Train Tour to learn about the island's history and culture. Hop off at the Key West Lighthouse and Keeper's Quarters Museum for a panoramic view of the island.
Afternoon
For lunch, savor the flavors of the Caribbean at Bien Caribbean Latino. Afterward, visit the Key West Shipwreck Treasure Museum to discover the maritime history of Key West and enjoy the entertaining reenactments.
Evening
In the evening, indulge in a unique dining experience at Better Than Sex - A Dessert Restaurant Key West. Afterward, join the Key West Ghosts & Gravestones Guided Trolley Tour for a spine-tingling journey through the island's haunted past.
Bedtime
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Adventure on the Water

Morning
Enjoy a leisurely breakfast at Cafe Marquesa before embarking on the Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks. Explore the crystal-clear waters, kayak through mangroves, and enjoy a delicious lunch on a sandbar.
Afternoon
After the kayak tour, head to Smathers Beach for some relaxation and water activities. You can also grab a quick snack at the beachside concession stand. In the afternoon, take a guided tour of the Key West Aquarium to learn about the diverse marine life of the region.
Evening
As the day winds down, experience the Key West Sunset Party Cruise by Catamaran. Enjoy music, drinks, and the lively atmosphere as you sail into the sunset. Conclude your day with a delightful dinner at La Creperie French Cafe.
Bedtime
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Exploring Key West's Culinary Scene

Morning
Start your day with a delicious breakfast at The Flaming Buoy Filet Co.. Then, embark on the Key West Southernmost Food and Cultural Walking Tour to discover the island's culinary delights and learn about its cultural heritage.
Afternoon
For lunch, head to El Siboney Restaurant for authentic Cuban cuisine. Afterward, visit the Key West Butterfly and Nature Conservatory to admire the beautiful butterflies and tropical plants.
Evening
Conclude your Key West adventure with a memorable dinner at Louie's Backyard, known for its Caribbean-inspired dishes and oceanfront setting. Afterward, take a leisurely stroll to the Southernmost Point of the Continental USA to capture the iconic landmark at sunset.
Bedtime
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