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Key West, Florida

5-day Key West Road Trip with Fishing Itinerary

Published: 2023 Oct 24
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Exploring Key West

Morning
Start your day with a delicious breakfast at Blue Heaven, known for its unique atmosphere and mouthwatering dishes. After breakfast, embark on the Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour to get an overview of the city's top attractions.
Afternoon
For lunch, head to Santiago's Bodega, a local favorite known for its tapas and vibrant atmosphere. Afterward, satisfy your adventurous side with the Key West Jet Ski Island Tour, where you'll explore the beautiful waters surrounding Key West.
Evening
Enjoy a relaxing dinner at El Siboney Restaurant, a family-owned Cuban restaurant that serves authentic and flavorful dishes. End the evening with a Key West Sunset Party Cruise by Catamaran, where you can enjoy stunning views of the sunset while sipping on tropical drinks.
Bedtime
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Snorkeling and Historical Sites

Morning
Start your day with a refreshing breakfast at Garbo's Grill, known for its delicious breakfast burritos. Afterward, embark on the Key West 3-Hour Coral Reef Snorkeling adventure to explore the vibrant underwater world of Key West.
Afternoon
For lunch, indulge in Caribbean flavors at Bien Caribbean Latino, where you can enjoy dishes like jerk chicken and plantains. Afterward, visit historical sites such as the Ernest Hemingway Home and Museum and the Harry S. Truman Little White House.
Evening
Enjoy a waterfront dinner at Nine One Five, known for its innovative cuisine and cozy atmosphere. After dinner, take a leisurely stroll along Mallory Square to experience the lively atmosphere and catch street performances.
Bedtime
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Fishing Adventure

Morning
Start your day with a hearty breakfast at The Flaming Buoy Filet Co., known for its creative dishes and friendly service. After breakfast, embark on a thrilling Key West Sandbar Excursion & Kayak Tour with Lunch & Drinks to explore the pristine sandbars and enjoy fishing opportunities.
Afternoon
For lunch, head to Louie's Backyard, a waterfront restaurant that offers a diverse menu with fresh seafood options. Afterward, continue your fishing adventure with the Key West Dolphin Watching and Snorkeling Eco Cruise Tour, where you can spot dolphins and snorkel in the crystal-clear waters.
Evening
Enjoy a seafood feast at Firefly Key West, known for its fresh seafood and charming ambiance. After dinner, unwind with live music and a Key West 2-Hour Sunset Sail with Live Music experience, where you can enjoy the beautiful sunset while listening to live tunes.
Bedtime
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Exploring Marathon

Morning
Start your day with a delicious breakfast at La Trattoria Oceanside, a waterfront restaurant that serves Italian cuisine with a tropical twist. After breakfast, visit the Florida Keys National Marine Sanctuary to learn about the unique marine life and conservation efforts.
Afternoon
For lunch, head to Hideaway Cafe, a cozy cafe known for its sandwiches and homemade desserts. Afterward, explore the Crane Point Museum & Nature Center, where you can hike through nature trails and learn about the local ecosystem.
Evening
Enjoy a seafood dinner at Sunset Grille & Raw Bar, a waterfront restaurant that offers stunning sunset views and a variety of seafood dishes. End the evening with a relaxing walk along the beach at Smathers Beach.
Bedtime
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Fishing in Islamorada

Morning
Start your day with a delicious breakfast at Wahoo's Bar and Grill, a waterfront restaurant known for its breakfast burritos and ocean views. After breakfast, embark on a thrilling Islamorada Deep Sea Fishing Charter to experience world-class fishing in the waters of Islamorada.
Afternoon
For lunch, head to Morada Bay Beach Cafe, a beachfront restaurant that offers a relaxed atmosphere and Caribbean-inspired cuisine. Afterward, visit the Theater of the Sea, where you can interact with marine animals and watch exciting shows.
Evening
Enjoy a seafood dinner at Pierre's Restaurant, an elegant restaurant known for its French-Caribbean fusion cuisine. After dinner, relax and unwind at Lorelei Cabana Bar and Restaurant, where you can enjoy live music and breathtaking sunset views over the water.
Bedtime
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