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Ultimate 16-Day Florida Keys Adventure Itinerary
Last updated: 2024 Jun 14Island Arrival and Sunset Sail
Morning
Arrive in Key West and start your adventure with a hearty breakfast at Pepe's Cafe, a local favorite. After breakfast, head to the iconic Southernmost Point of the Continental USA to take your first memorable photo of the trip. Then, enjoy a leisurely stroll along the historic Duval Street, exploring the unique shops and vibrant atmosphere.
Afternoon
For lunch, savor the island flavors at Blue Heaven, known for its delicious cuisine and laid-back ambiance. Post-lunch, immerse yourself in the marine life at the Key West Aquarium, followed by a visit to the historic Key West Shipwreck Treasure Museum to learn about the area's maritime history.
Evening
Witness the stunning Key West sunset on the Key West Sunset Party Cruise by Catamaran, complete with live music, a tropical atmosphere, and an open bar. Enjoy the vibrant entertainment and mingle with fellow travelers as the sun dips below the horizon.
Bedtime
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Southernmost Point of the Continental USA
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Duval Street
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Key West Aquarium
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Key West Shipwreck Treasure Museum
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Key West Sunset Party Cruise by Catamaran
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Snorkeling and Island Exploration
Morning
Start your day with a delicious breakfast at Half Shell Raw Bar, known for its fresh seafood and waterfront dining. After breakfast, gear up for an exciting morning of snorkeling on the Key West Reef Snorkel Morning Tour with Breakfast & Mimosas. Explore the colorful underwater world and spot a variety of marine life.
Afternoon
After the snorkeling adventure, enjoy a leisurely lunch at Southernmost Beach Café, where you can dine with a view of the ocean. Post-lunch, relax at the beautiful Smathers Beach, known for its sandy shores and calm waters. You can also opt for some beach activities or simply soak in the sun.
Evening
As the evening sets in, take a guided tour of the Key West Ghosts & Gravestones Guided Trolley Tour to uncover the island's haunted history. After the tour, enjoy a delightful dinner at The White Tarpon Bar & Restaurant, offering a cozy and intimate dining experience.
Bedtime
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Key West Reef Snorkel Morning Tour with Breakfast & Mimosas
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Smathers Beach
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Key West Ghosts & Gravestones Guided Trolley Tour
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Historic Sites and Sunset Celebration
Morning
Begin your day with a visit to the famous Mallory Square, where you can witness the vibrant street performers and local artisans. Grab a quick breakfast at Island Dogs Bar before hopping on the Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour to explore the island's historic landmarks at your own pace.
Afternoon
For lunch, head to Hot Tin Roof Restaurant and indulge in their delectable dishes with a view of the marina. After lunch, continue your trolley tour and make a stop at the Ernest Hemingway Home and Museum to learn about the famous writer's life and admire the resident six-toed cats.
Evening
Experience the lively Sunset Celebration at Mallory Square with live music, street performers, and a stunning sunset backdrop. After the celebration, enjoy a sumptuous dinner at Bagatelle, known for its elegant setting and French-inspired cuisine.
Bedtime
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Mallory Square
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Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour
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Ernest Hemingway Home and Museum
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Mallory Square
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Watersports and Culinary Delights
Morning
Fuel up for an adventurous day with breakfast at Mary Ellen's Bar & Restaurant, a local gem. Post-breakfast, head to the Do It All Watersports With Parasailing location for an action-packed morning. Enjoy parasailing, jet skiing, and other water activities in the beautiful Key West waters.
Afternoon
After the thrilling watersports, grab a casual lunch at Jack Flats, a laid-back spot with a diverse menu. Spend your afternoon at leisure, exploring the shops and galleries of the Key West Historic District or relaxing at a nearby beach.
Evening
For dinner, indulge in the flavors of the Caribbean at Pirate's Cove Key West, where the seafood and tropical drinks are top-notch. Cap off the evening with a leisurely stroll along the Edward B. Knight Pier, enjoying the sea breeze and the sight of boats returning to the harbor.
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Key West Multiple Water Sports Excursion with Lunch & Beer
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Key West Historic District
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Edward B. Knight Pier
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Tranquil Gardens and Sunset Serenade
Morning
Start your day with a visit to the serene Key West Butterfly and Nature Conservatory, where you can admire the colorful butterflies and lush tropical plants. Afterward, enjoy a delightful breakfast at Old Town Tavern & Beer Garden, known for its relaxed atmosphere and wide selection of brews.
Afternoon
Spend your afternoon exploring the beautiful grounds of the Key West Lighthouse and Keeper's Quarters Museum, learning about the island's maritime history and enjoying panoramic views from the top. For lunch, head to Schooner Wharf Bar for a casual meal with a waterfront view.
Evening
Dine in the enchanting courtyard of The White Tarpon Bar & Restaurant, where the menu features fresh, local ingredients. After dinner, take a leisurely stroll to Mallory Square and enjoy the nightly Sunset Celebration, complete with live music and street performers.
Bedtime
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Key West Butterfly and Nature Conservatory
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Key West Lighthouse and Keeper's Quarters Museum
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Mallory Square
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Historical Journey and Evening Sail
Morning
Begin with a hearty breakfast at Half Shell Raw Bar, a local favorite. Then, embark on a historical journey with a visit to the Harry S. Truman Little White House, followed by a walk through the Key West Cemetery to learn about the island's unique burial traditions.
Afternoon
Enjoy a leisurely lunch at Blue Heaven, known for its eclectic cuisine and vibrant atmosphere. After lunch, explore the exhibits at the Mel Fisher Maritime Museum, where you can see artifacts from shipwrecks and learn about the history of treasure hunting in the Florida Keys.
Evening
Conclude your day with a memorable Key West 2-Hour Sunset Sail with Live Music. Relax on the deck of a beautiful sailboat, enjoy live music, and witness the breathtaking Key West sunset with a drink in hand.
Bedtime
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Harry S. Truman Little White House
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Key West Cemetery
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Mel Fisher Maritime Museum
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Key West 2-Hour Sunset Sail with Live Music
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Day of Relaxation and Fine Dining
Morning
Start your day with a leisurely breakfast at Southernmost Beach Café, where you can enjoy the ocean view. After breakfast, spend the morning at the beach, soaking up the sun and taking a dip in the clear waters.
Afternoon
For lunch, head to Hot Tin Roof Restaurant, known for its elegant ambiance and delectable cuisine. After lunch, pamper yourself with a spa treatment at one of Key West's top spas, such as the Spa al Mare at Casa Marina or the The Spa at Sunset Key.
Evening
Dress up for a sophisticated dinner at Latitudes, located on the private island of Sunset Key. Enjoy a boat ride to the island and indulge in a memorable dining experience with impeccable service and a menu featuring fresh, local ingredients.
Bedtime
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Key West by Land and Sea
Morning
Enjoy a delicious breakfast at Blue Heaven, a quirky spot with a laid-back vibe. After breakfast, embark on the Key West Conch Train Tour to get an overview of the island's history and landmarks, including the famous Hemingway House and the Southernmost Point.
Afternoon
For lunch, head to The Stoned Crab, where you can dine on fresh seafood in a relaxed setting. After lunch, take to the water on a Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks. Paddle through the crystal-clear waters and enjoy a picnic on a secluded sandbar.
Evening
Dine at The Flaming Buoy Filet Co., a hidden gem known for its creative dishes and intimate atmosphere. After dinner, take a leisurely stroll through the Key West Historic Seaport, where you can admire the boats and watch the sunset.
Bedtime
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Key West Conch Train Tour
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Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks
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Thrills and Chills
Morning
Start your day with breakfast at Mary Ellen's Bar & Restaurant, a local spot with a laid-back vibe. After breakfast, get your adrenaline pumping with a Key West Jet Ski Island Tour. Explore the waters around Key West and visit some of the nearby islands.
Afternoon
After the jet ski tour, grab a quick bite at McKee's Tiki Bar, a casual spot with great drinks. Spend the rest of your afternoon at Fort Zachary Taylor, where you can relax on the beach or take a tour of the historic fort.
Evening
Enjoy a dinner with a view at The Commodore Waterfront Restaurant, located on the Key West Bight Marina. After dinner, take a Key West Sunset Sailing Trip with Open Bar, Food and Music and watch the sun sink below the horizon as you sail the waters of Key West.
Bedtime
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Key West Jet Ski Island Tour
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From Fairbanks Chena Hot Springs Northern Lights Tour
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Key West Sunset Sailing Trip with Open Bar, Food and Music
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Underwater Wonders and Culinary Delights
Morning
Start your day with a delicious breakfast at Island Dogs Bar, a laid-back spot with a diverse menu. After breakfast, head out for a morning of snorkeling on the Key West 3-Hour Coral Reef Snorkeling. Explore the vibrant coral reefs and encounter a variety of marine life.
Afternoon
After the snorkeling adventure, enjoy a leisurely lunch at Tavern N Town, known for its upscale dining experience. Post-lunch, visit the Key West Art & Historical Society Custom House Museum to learn about the island's rich history and cultural heritage.
Evening
Dine at The Flaming Buoy Filet Co., a hidden gem known for its creative dishes and intimate atmosphere. After dinner, take a leisurely stroll through the Key West Historic Seaport, where you can admire the boats and watch the sunset.
Bedtime
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Key West 3-Hour Coral Reef Snorkeling
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Island Adventure and Sunset Soiree
Morning
Start your day with a delicious breakfast at Willie T's, a lively spot with a diverse menu. After breakfast, head to the Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour to explore the island's historic landmarks at your own pace. Make sure to hop off at the Key West Butterfly and Nature Conservatory to admire the colorful butterflies and lush tropical plants.
Afternoon
For lunch, enjoy the casual atmosphere and fresh seafood at Half Shell Raw Bar. After lunch, 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.
Evening
Dine at The Commodore Waterfront Restaurant, located on the Key West Bight Marina. After dinner, take a Key West Sunset Party Cruise by Catamaran and enjoy live music, a tropical atmosphere, and an open bar as you witness the stunning Key West sunset.
Bedtime
Find amazing hotels in Key West, Florida.
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Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour
click to access prices
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Key West Butterfly and Nature Conservatory
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Key West Lighthouse and Keeper's Quarters Museum
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Key West Sunset Party Cruise by Catamaran
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Oceanic Encounters and Cultural Delights
Morning
Begin your day with a delightful breakfast at The Stoned Crab, where you can enjoy fresh seafood with a view. After breakfast, embark on the Key West Dolphin Watching and Snorkeling Eco Cruise Tour to observe dolphins in their natural habitat and snorkel in the pristine waters of Key West.
Afternoon
After the cruise, head to Mallory Square and explore the shops and galleries in the area. For lunch, visit Sloppy Joe's, a Key West institution known for its lively atmosphere and classic American fare. After lunch, take a guided tour of the Key West Aquarium to learn about the diverse marine life of the Florida Keys.
Evening
Dine at The Flaming Buoy Filet Co., a hidden gem known for its creative dishes and intimate atmosphere. After dinner, take a leisurely stroll to Mallory Square and enjoy the nightly Sunset Celebration, complete with live music and street performers.
Bedtime
Find amazing hotels in Key West, Florida.
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Key West Dolphin Watching and Snorkeling Eco Cruise Tour
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Mallory Square
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Key West Aquarium
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Mallory Square
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Island History and Culinary Delights
Morning
Start your day with a visit to the Key West Shipwreck Treasure Museum, where you can learn about the island's maritime history and see artifacts from shipwrecks. After the museum, enjoy a delicious breakfast at The Stoned Crab, known for its fresh seafood and waterfront dining.
Afternoon
After breakfast, take a guided tour of the Harry S. Truman Little White House, the winter White House for President Truman. For lunch, head to The Commodore Waterfront Restaurant and enjoy a meal with a view of the marina.
Evening
Dine at The Flaming Buoy Filet Co., a hidden gem known for its creative dishes and intimate atmosphere. After dinner, take a leisurely stroll through the Key West Historic Seaport, where you can admire the boats and watch the sunset.
Bedtime
Find amazing hotels in Key West, Florida.
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Key West Shipwreck Treasure Museum
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Harry S. Truman Little White House
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Island Relaxation and Farewell Feast
Morning
Enjoy a leisurely breakfast at The Stoned Crab, where you can savor fresh seafood with a view of the marina. After breakfast, spend the morning at Fort Zachary Taylor, where you can relax on the beach, explore the fort, and take in the natural beauty of the area.
Afternoon
For lunch, head to The Commodore Waterfront Restaurant and enjoy a meal with a view of the Key West Bight Marina. After lunch, take a guided tour of the Key West Cemetery to learn about the island's unique burial traditions and the famous residents who are laid to rest there.
Evening
Dine at The Flaming Buoy Filet Co., a hidden gem known for its creative dishes and intimate atmosphere. After dinner, take a leisurely stroll through the Key West Historic Seaport, where you can admire the boats and watch the sunset.
Bedtime
Find amazing hotels in Key West, Florida.
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From Fairbanks Chena Hot Springs Northern Lights Tour
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Key West Cemetery
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Island Farewell and Sunset Spectacle
Morning
Start your last day in Key West with a delicious breakfast at The Stoned Crab, where you can enjoy fresh seafood with a view of the marina. After breakfast, take a walk to the Southernmost Point of the Continental USA and capture one final photo to remember your time in Key West.
Afternoon
For lunch, head to The Commodore Waterfront Restaurant and enjoy a meal with a view of the Key West Bight Marina. After lunch, spend your afternoon at Smathers Beach, soaking up the sun and enjoying the beautiful Key West weather.
Evening
Dine at The Flaming Buoy Filet Co., a hidden gem known for its creative dishes and intimate atmosphere. After dinner, take a leisurely stroll through the Key West Historic Seaport, where you can admire the boats and watch the sunset.
Bedtime
Find amazing hotels in Key West, Florida.
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Southernmost Point of the Continental USA
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Smathers Beach
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Island Farewell and Sunset Spectacle
Morning
Start your last day in Key West with a delicious breakfast at The Stoned Crab, where you can enjoy fresh seafood with a view of the marina. After breakfast, take a walk to the Southernmost Point of the Continental USA and capture one final photo to remember your time in Key West.
Afternoon
For lunch, head to The Commodore Waterfront Restaurant and enjoy a meal with a view of the Key West Bight Marina. After lunch, spend your afternoon at Smathers Beach, soaking up the sun and enjoying the beautiful Key West weather.
Evening
Dine at The Flaming Buoy Filet Co., a hidden gem known for its creative dishes and intimate atmosphere. After dinner, take a leisurely stroll through the Key West Historic Seaport, where you can admire the boats and watch the sunset.
Bedtime
Find amazing hotels in Key West, Florida.
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Southernmost Point of the Continental USA
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Smathers Beach
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