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Two-Day Itinerary in Key West

Viewed by 65 travelers

Day 1: Saturday, November 25, 2023

Morning - Explore Old Town

Start your day by exploring the charming streets of Old Town Key West. Visit the Ernest Hemingway Home and Museum, where the famous writer lived and wrote some of his greatest works. Wander through the beautiful gardens and meet the six-toed cats that roam the property. Afterward, make your way to the Southernmost Point of the United States for a great photo opportunity. This monumental buoy marks the southernmost tip of the continental United States and is a must-visit when in Key West.

  • Ernest Hemingway Home and Museum: Cost estimate - $15, Time spent - 1-2 hours
  • Southernmost Point: Free, Time spent - 30 minutes
Afternoon - Water Adventure

Head to Mallory Square to embark on a thrilling snorkeling adventure. Key West is home to the third-largest coral reef system in the world, offering vibrant underwater landscapes teeming with marine life. Book a snorkeling tour and explore the crystal-clear waters, swimming alongside colorful fish and maybe even encountering sea turtles and dolphins. After your snorkeling adventure, enjoy a delicious lunch at one of the waterfront restaurants in Mallory Square.

  • Snorkeling tour: Cost estimate - $50, Time spent - 3 hours
  • Lunch at Mallory Square: Cost estimate - $20, Time spent - 1 hour
Evening - Sunset Celebration

End your day with the famous Key West sunset celebration at Mallory Square. Join locals and visitors alike as they gather to watch the breathtaking sunset over the Gulf of Mexico. Enjoy live music, street performers, and browse the local shops and art stalls. Afterward, indulge in a delicious seafood dinner at one of the waterfront restaurants while enjoying the relaxing ambiance of Key West's evening atmosphere.

  • Sunset celebration at Mallory Square: Free, Time spent - 2 hours
  • Seafood dinner: Cost estimate - $30, Time spent - 1-2 hours

Day 2: Sunday, November 26, 2023

Morning - Fort Zachary Taylor Historic State Park

Start your second day by visiting Fort Zachary Taylor Historic State Park. Explore the beautiful beach, go for a leisurely swim, or take a walk along the nature trails that wind through the park. Don't miss the opportunity to explore the historic fort, which played a significant role in the Civil War. The park offers a serene and scenic setting, perfect for unwinding and enjoying the natural beauty of Key West.

  • Fort Zachary Taylor Historic State Park: Cost estimate - $7, Time spent - 2-3 hours
Afternoon - Duval Street

Spend your afternoon exploring Duval Street, Key West's vibrant and lively main street. With its colorful buildings, quirky shops, and lively bars, Duval Street offers something for everyone. Browse through unique boutiques, pick up souvenirs, and sample delicious local cuisine. Make a stop at the Key West Butterfly and Nature Conservatory, where you can immerse yourself in the beauty of tropical butterflies and exotic birds.

  • Duval Street: Cost estimate - Varies (shopping and dining), Time spent - 2-3 hours
  • Key West Butterfly and Nature Conservatory: Cost estimate - $15, Time spent - 1-2 hours
Evening - Sunset Sail

End your Key West getaway with a romantic sunset sail aboard a sailboat or catamaran. Enjoy the breathtaking views as the sun dips below the horizon, painting the sky with hues of orange and pink. Savor complimentary drinks and snacks while feeling the gentle ocean breeze. This magical experience is the perfect way to conclude your visit to Key West.

  • Sunset sail: Cost estimate - $50, Time spent - 2 hours

Hidden Gems and Local Favorites

Key West is full of hidden gems and local favorites. One such gem is the Key West Lighthouse and Keeper's Quarters Museum. Climb to the top of the lighthouse for panoramic views of the island and learn about the fascinating maritime history. Another local favorite is the Key West Cemetery, which may seem unusual, but it is a peaceful and historically significant place to explore. Additionally, locals love visiting Smathers Beach, a less crowded alternative to the popular tourist beaches. Relax on the sandy shores and soak up the sun away from the hustle and bustle.

For more information, check out hotel and flight prices on Kayak.com.

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