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5-Day Key West Adventure: Beaches, History, and Culinary Delights

Viewed by 86 travelers

Day 1: Arrival and Old Town

Key West, Florida on September 4, 2025

9:00am

Breakfast at Blue Heaven

Enjoy a delicious breakfast at Blue Heaven, known for its tropical outdoor seating and signature dishes like coconut pancakes and lobster Benedict. It's a perfect way to start your Key West adventure.
USD20, 1h

10:30am

Stroll through Old Town Key West

Explore the charming streets of Old Town, marvel at the historic architecture, visit colorful shops, and soak in the island's vibrant culture.
Free, 2h

12:30pm

Lunch at El Siboney

Savor authentic Cuban cuisine at El Siboney, a local favorite offering hearty and flavorful dishes in a casual setting.
USD15, 1h

2:00pm

Visit Ernest Hemingway Home and Museum

Tour the famous Ernest Hemingway Home to learn about the writer's life in Key West and admire the lush gardens and six-toed cats.
USD17, 1h30m

4:00pm

Relax at Mallory Square

Enjoy the vibrant atmosphere of Mallory Square, famous for its sunset celebrations and street performers.
Free, 2h

7:00pm

Dinner at Latitude's Restaurant

Dine at Latitude's, an upscale restaurant on Sunset Key offering exquisite seafood and stunning ocean views, perfect for a memorable first night.
USD50, 2h
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Day 2: Beaches and Water Activities

Key West, Florida on September 5, 2025

8:00am

Breakfast at Sarabeth's Key West

Start your day with a hearty breakfast featuring classic American dishes and fresh juices at Sarabeth's.
USD18, 1h

9:30am

Beach time at Fort Zachary Taylor Historic State Park

Relax or swim at one of Key West's best beaches, known for its clear water, picnic areas, and historic Civil War fort to explore.
USD6, 3h

1:00pm

Lunch at Salute! On The Beach

Enjoy fresh seafood and tropical cocktails at this beachfront restaurant, offering casual island dining.
USD25, 1h

2:30pm

Snorkeling tour at Key West Shipwreck Museum

Join a snorkeling adventure to explore coral reefs and marine life, departing near the Key West Shipwreck Museum.
USD70, 3h

6:00pm

Sunset sail

Take a relaxing sunset sailing cruise departing from the historic harbor, enjoying panoramic views and cool breezes.
USD60, 2h

8:30pm

Dinner at The Flaming Buoy Filet Co.

Enjoy innovative American cuisine with island flair in a lively atmosphere, known for fresh fish and unique sauces.
USD40, 2h
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Day 3: History and Museums

Key West, Florida on September 6, 2025

8:30am

Breakfast at Cuban Coffee Queen

Fuel up with strong Cuban coffee and breakfast bites at this popular local spot.
USD8, 30m

9:00am

Key West Lighthouse and Keeper’s Quarters Museum

Climb the lighthouse for spectacular views and explore the keeper's quarters to learn about maritime history.
USD12, 1h

10:30am

Mel Fisher Maritime Museum

Discover treasures and artifacts from shipwrecks recovered by legendary diver Mel Fisher, showcasing Key West's maritime past.
USD12, 1h

12:00pm

Lunch at Garbo’s Grill

Savor food truck favorites like fish tacos and burgers at the popular Garbo's Grill near Duval Street.
USD15, 1h

1:30pm

The Key West Butterfly and Nature Conservatory

Walk through a tropical garden filled with vibrant butterflies, exotic birds, and flowering plants.
USD16, 1h

3:00pm

Harry S. Truman Little White House

Tour the historic winter White House of President Truman and learn about its significance during his presidency.
USD20, 1h30m

5:00pm

Explore Duval Street

Stroll along Duval Street for shopping, bars, and entertainment as the evening comes alive.
Free, 2h

7:30pm

Dinner at Latitudes

Enjoy an exquisite meal with breathtaking ocean views on Sunset Key, booking ahead is recommended.
USD55, 2h
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Day 4: Nature and Outdoor Adventures

Key West, Florida on September 7, 2025

7:30am

Breakfast at Cuban Coffee Queen

Grab a quick coffee and pastelito to start an active outdoor day.
USD8, 30m

8:00am

Kayaking and Eco Tour at Great White Heron National Wildlife Refuge

Spend the morning kayaking through mangroves and spotting wildlife in this protected refuge, tours usually last 3-4 hours.
USD80, 4h

12:30pm

Lunch at Banana Cafe

Enjoy French-inspired cuisine in a cozy setting, perfect for refueling after outdoor activities.
USD30, 1h

2:00pm

Relax at Higgs Beach

Spend a relaxing afternoon swimming and sunbathing at Higgs Beach, known for its calm waters and nearby pier.
Free, 2h

4:30pm

Visit The Eco-Discovery Center

Learn about the Everglades and Florida Keys ecosystems at this interactive and educational center.
Free, 1h

6:00pm

Sunset at Sunset Pier

Watch the iconic Key West sunset from Sunset Pier, enjoying live music and casual atmosphere.
Free, 1h30m

8:00pm

Dinner at Louie's Backyard

Dine on fresh seafood and gourmet fare with oceanfront views in this elegant yet relaxed setting.
USD50, 2h
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Day 5: Relax and Departure

Key West, Florida on September 8, 2025

8:00am

Breakfast at Cuban Coffee Queen

Enjoy a final Cuban coffee and breakfast sandwich before checking out, a local staple.
USD8, 30m

9:00am

Last walk through Key West Butterfly and Nature Conservatory or Beach walk

Revisit the peaceful butterfly conservatory or enjoy a relaxing stroll along the nearby beach before departure.
USD16 or Free, 1h

10:30am

Check out and depart

Prepare for your departure from Key West, taking with you wonderful memories of your trip.
Variable, N/A
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