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Ultimate 5-Day Key West Adventure

Ultimate 5-Day Key West Adventure Itinerary

Last updated: 2024 Jun 14

Island Introduction and Sunset Sail

Morning
Start your Key West adventure with a delightful breakfast at Blue Heaven, known for its unique ambiance and delicious cuisine. After breakfast, head to Mallory Square to witness the vibrant street performers and take in the stunning views of the ocean.
Afternoon
For lunch, enjoy the fresh seafood at Hogfish Bar & Grill, a local favorite. Post lunch, 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 the historic district, Key West Aquarium, and more.
Evening
Dine at Latitudes on Sunset Key for a memorable dinner experience. Later, embark on the Key West 2-Hour Sunset Sail on Schooner America 2.0 to witness a breathtaking Key West sunset while enjoying complimentary drinks and live music.
Bedtime
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Snorkeling and Culinary Delights

Morning
Start your day with a delicious breakfast at Banana Cafe Key West. After breakfast, gear up for an exciting Key West 3-Hour Coral Reef Snorkeling adventure. Explore the vibrant underwater world and spot colorful marine life.
Afternoon
After the snorkeling trip, enjoy a well-deserved lunch at Garbo's Grill, known for its gourmet food truck offerings. Spend the rest of the afternoon relaxing at Smathers Beach, one of the best beaches in Key West.
Evening
For dinner, head to Nine One Five, a contemporary restaurant with a diverse menu. Afterward, take a leisurely stroll along the famous Duval Street and explore its lively bars, shops, and galleries.
Bedtime
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Historic Sites and Sunset Celebrations

Morning
Enjoy a delightful breakfast at Cafe Marquesa, known for its elegant setting and culinary excellence. Post breakfast, visit the iconic Southernmost Point of the Continental USA and take a photo at this landmark.
Afternoon
Have lunch at La Creperie French Cafe, where you can savor a variety of sweet and savory crepes. Afterward, immerse yourself in history with visits to the Ernest Hemingway Home and Museum and the Key West Lighthouse and Keeper's Quarters Museum.
Evening
Dine at The Flaming Buoy Filet Co., a hidden gem known for its creative dishes. As the evening approaches, join the lively crowd at Mallory Square for the famous Key West Sunset Celebration. Witness street performers, local artisans, and the stunning sunset backdrop.
Bedtime
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Water Adventures and Evening Elegance

Morning
Start with a hearty breakfast at Azur Restaurant, offering a taste of the Mediterranean. After breakfast, set out for an action-packed morning with the Key West Dolphin Watching, Snorkeling, and Sunset Cruise. Spot dolphins in their natural habitat and enjoy the beautiful waters.
Afternoon
For lunch, head to Mangia Mangia Pasta Cafe for a satisfying Italian meal. Post lunch, indulge in a relaxing Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks. Paddle through the crystal-clear waters and enjoy the serene surroundings.
Evening
Dress up for an elegant dinner at Martin's Restaurant & Lounge, known for its sophisticated ambiance and culinary delights. After dinner, experience the vibrant nightlife of Key West with a visit to the Overseas Highway, where you can explore the bars and entertainment venues.
Bedtime
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Morning Adventure and Farewell Fun

Morning
Enjoy a final Key West breakfast at Firefly Key West, offering a blend of local flavors. After breakfast, take to the skies with an exhilarating Key West Parasailing Flights experience. Soar above the island and take in panoramic views.
Afternoon
For your last lunch in Key West, visit Better Than Sex - A Dessert Restaurant Key West for a unique dining experience focused on decadent desserts. Afterward, spend your afternoon at Dry Tortugas National Park, exploring the historic fort and enjoying the pristine beach.
Evening
Conclude your Key West journey with a memorable dinner at Louie's Backyard, an iconic restaurant with a stunning oceanfront setting. Reflect on your trip as you enjoy the cuisine and perhaps a cocktail. As the night progresses, consider joining a local event or live music performance to end your trip on a high note.
Bedtime
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