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Ultimate Key West Adventure and Relaxation Itinerary
Last updated: 2024 Jun 14Arrival and Island Introduction
Morning
Welcome to Key West! Start your day with a delightful breakfast at Blue Heaven, known for its unique atmosphere and delicious cuisine. After breakfast, take a leisurely stroll through the historic Key West Historic District, immersing yourself in the charming architecture and rich history of the area.
Afternoon
For lunch, head to Banana Cafe Key West for a taste of Caribbean-inspired dishes. Afterward, hop on the Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour to get an overview of the island's top attractions, including Mallory Square, Duval Street, and the Southernmost Point of the Continental USA.
Evening
Enjoy a relaxing evening at Latitudes on Sunset Key, where you can savor a gourmet dinner while watching the sunset over the water. After dinner, take a leisurely walk along the waterfront and soak in the island's laid-back atmosphere.
Bedtime
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Snorkeling and Sunset Sailing
Morning
Start your day with a delicious breakfast and mimosas on the Key West Reef Snorkel Morning Tour with Breakfast & Mimosas. Immerse yourself in the vibrant underwater world of the Florida Keys National Marine Sanctuary.
Afternoon
For lunch, enjoy fresh seafood at Hogfish Bar & Grill, a local favorite. In the afternoon, embark on the Key West Sunset Sailing Trip with Open Bar, Food and Music, where you can relax, enjoy the open bar, and watch the sun dip below the horizon.
Evening
After the sunset cruise, head to Nine One Five for a sophisticated dinner experience. End the evening with a stroll along the lively Duval Street, where you can explore the shops, galleries, and nightlife.
Bedtime
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Historic Sites and Dolphin Watching
Morning
Enjoy a hearty breakfast at Mangia Mangia Pasta Cafe before embarking on the Key West Conch Train Tour, which will take you to key historic sites such as the Harry S. Truman Little White House and the Ernest Hemingway Home and Museum.
Afternoon
For lunch, try the Cuban cuisine at El Siboney Restaurant. In the afternoon, set out on the Key West Dolphin Watching, Snorkeling, and Sunset Cruise, where you can observe dolphins in their natural habitat and snorkel in the crystal-clear waters.
Evening
After the cruise, dine at Firefly Key West, known for its innovative dishes and charming ambiance. Then, take a leisurely walk to the Mallory Square to witness the famous Key West Sunset Celebration.
Bedtime
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Adventure and Relaxation
Morning
Start your day with a delicious breakfast at La Creperie French Cafe. Then, embark on the Key West Jet Ski Island Tour, where you can zip through the waters surrounding the island and enjoy the thrill of the open sea.
Afternoon
For lunch, head to Blackfin Bistro for a taste of their fresh seafood dishes. In the afternoon, unwind at Smathers Beach, where you can relax on the sandy shore and soak up the sun.
Evening
Enjoy a casual dinner at Garbo's Grill, known for its gourmet food truck fare. Afterward, take a leisurely stroll along the Edward B. Knight Pier and enjoy the peaceful evening atmosphere.
Bedtime
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Sunset Sails and Local Flavors
Morning
Indulge in a delicious breakfast at The Flaming Buoy Filet Co., known for its creative dishes and welcoming atmosphere. After breakfast, embark on the Key West 2-Hour Sunset Sail with Live Music, where you can enjoy the sunset while listening to live music.
Afternoon
For lunch, try the Mediterranean-inspired cuisine at Azur Restaurant. In the afternoon, explore the local art scene at the Key West Art & Historical Society Custom House Museum and the Key West Lighthouse and Keeper's Quarters Museum.
Evening
Enjoy a memorable dinner at Martin's Restaurant & Lounge, known for its elegant ambiance and exceptional cuisine. After dinner, take a leisurely walk through the Key West Cemetery and learn about the island's unique history.
Bedtime
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Island Adventure and Relaxation
Morning
Start your day with a delicious breakfast at Better Than Sex - A Dessert Restaurant Key West, known for its decadent desserts and romantic ambiance. Then, embark on the Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks, where you can explore the island's hidden gems and enjoy a gourmet picnic on a secluded sandbar.
Afternoon
For lunch, try the Latin flavors at Bien Caribbean Latino. In the afternoon, relax at the Key West Butterfly and Nature Conservatory, where you can admire the colorful butterflies and lush tropical plants.
Evening
Enjoy a casual dinner at Santiago's Bodega, known for its tapas and lively atmosphere. Afterward, take a leisurely walk along the Key West Harbor Walk and enjoy the views of the marina.
Bedtime
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Farewell and Island Memories
Morning
Enjoy a leisurely breakfast at Cafe Marquesa, known for its elegant setting and gourmet cuisine. Then, spend the morning at the Key West Aquarium, where you can observe a variety of marine life and learn about the island's ecosystem.
Afternoon
For lunch, try the Caribbean-inspired dishes at Sunset Pier. In the afternoon, take a guided tour of the Key West Shipwreck Treasure Museum and learn about the island's maritime history.
Evening
End your trip with a memorable dinner at Louie's Backyard, known for its waterfront dining and stunning sunset views. After dinner, take a leisurely walk along the Key West Historic Seaport and enjoy the vibrant atmosphere of the waterfront.
Bedtime
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