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6-Day Key West Getaway: Beach, History, and Island Charm

Viewed by 70 travelers

Day 1: Arrival and Old Town

Key West, Florida on September 4, 2025

9:00am

Breakfast at Blue Heaven

Enjoy a delightful breakfast at Blue Heaven, famous for its relaxed tropical atmosphere and unique dishes like lobster Benedict.
USD20, 1h

10:30am

Stroll through Old Town Key West

Discover the charms of Old Town with historic homes, quirky shops, and vibrant street scenes that embody Key West’s spirit.
Free, 2h

12:30pm

Lunch at El Siboney

Experience authentic Cuban flavors at El Siboney, a casual spot beloved by locals for generous portions.
USD15, 1h

2:00pm

Visit Ernest Hemingway Home and Museum

Tour the historic home of Ernest Hemingway, where you can see lush gardens and meet the famous six-toed cats.
USD17, 1h30m

4:00pm

Relax at Mallory Square

Enjoy the lively atmosphere and prepare for the sunset celebration, featuring local performers and artisans.
Free, 2h

7:00pm

Dinner at Latitude's Restaurant

Savor exquisite seafood with stunning sunset views at Latitude's on Sunset Key; reservations recommended.
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 hearty American breakfast classics and fresh juices at Sarabeth's.
USD18, 1h

9:30am

Beach day at Fort Zachary Taylor Historic State Park

Swim, sunbathe, and explore the Civil War-era fort at one of Key West's most popular beaches.
USD6, 3h

1:00pm

Lunch at Salute! On The Beach

Dine on fresh seafood and tropical drinks just steps from the beach in a laid-back setting.
USD25, 1h

2:30pm

Snorkeling tour

Explore vibrant coral reefs on a snorkel tour departing near the Key West Shipwreck Museum, lasting about 3 hours.
USD70, 3h

6:00pm

Sunset sail

Relax as you sail along the coast during sunset, with breathtaking island views and cool breezes.
USD60, 2h

8:30pm

Dinner at The Flaming Buoy Filet Co.

Enjoy creative American dishes with island influences in a cozy and friendly atmosphere.
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

Grab a strong Cuban coffee and tasty breakfast items to fuel your day.
USD8, 30m

9:00am

Key West Lighthouse and Keeper’s Quarters Museum

Climb to the top for panoramic views then explore the keeper's quarters to learn about island maritime history.
USD12, 1h

10:30am

Mel Fisher Maritime Museum

See amazing shipwreck treasures and discover local maritime lore.
USD12, 1h

12:00pm

Lunch at Garbo’s Grill

Enjoy delicious fish tacos and other street food favorites from this popular food truck.
USD15, 1h

1:30pm

The Key West Butterfly and Nature Conservatory

Wander a tropical oasis of butterflies, birds, and lush plants for a serene afternoon.
USD16, 1h

3:00pm

Harry S. Truman Little White House

Tour President Truman’s winter retreat and learn about its historical significance.
USD20, 1h30m

5:00pm

Explore Duval Street

Experience shopping, entertainment, and nightlife along Key West’s lively main street.
Free, 2h

7:30pm

Dinner at Latitudes

Treat yourself to gourmet dining with spectacular ocean views on Sunset Key; booking ahead is a must.
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

Enjoy a quick Cuban coffee and pastelito to prepare for a day outdoors.
USD8, 30m

8:00am

Kayaking and Eco Tour at Great White Heron National Wildlife Refuge

Explore mangrove tunnels and wildlife on a guided kayaking tour lasting 3-4 hours.
USD80, 4h

12:30pm

Lunch at Banana Cafe

Relax over French-inspired fare in a charming environment to refuel after your adventure.
USD30, 1h

2:00pm

Relax at Higgs Beach

Spend the afternoon swimming and unwinding at a tranquil, family-friendly beach.
Free, 2h

4:30pm

Visit The Eco-Discovery Center

Discover interactive exhibits about the unique ecosystems of the Everglades and Florida Keys.
Free, 1h

6:00pm

Sunset at Sunset Pier

Enjoy live music and sunset views from this popular waterfront pier on the island.
Free, 1h30m

8:00pm

Dinner at Louie's Backyard

Dine on gourmet seafood and seasonal dishes in an elegant oceanfront setting.
USD50, 2h
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Day 5: Leisure and Exploration

Key West, Florida on September 8, 2025

8:00am

Breakfast at Cuban Coffee Queen

Enjoy a fresh Cuban coffee and breakfast sandwich to start your leisurely day.
USD8, 30m

9:00am

Kayak or paddleboard rental

Rent a kayak or paddleboard to explore the calm waters around Key West at your own pace.
USD40, 2h

11:30am

Brunch at Firefly

Indulge in creative brunch dishes with island flair in one of Key West’s best-rated restaurants.
USD30, 1h30m

1:00pm

Visit Key West Shipwreck Museum

Learn about treasure hunters and shipwreck salvage in this interactive museum downtown.
USD15, 1h

2:30pm

Explore local galleries and shops

Spend the afternoon browsing art galleries and unique boutiques around the island.
Free, 2h

5:00pm

Relax with a sunset cocktail

Enjoy a cocktail at a waterfront bar like The Porch or Irish Kevin’s while watching the sun set.
USD15, 1h30m

7:00pm

Dinner at Santiago's Bodega

Savor creative tapas and wine in an intimate setting, perfect for your last night in Key West.
USD40, 2h
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Day 6: Relax and Departure

Key West, Florida on September 9, 2025

8:00am

Breakfast at Cuban Coffee Queen

Enjoy a final Cuban coffee and light breakfast before packing up for your departure.
USD8, 30m

9:00am

Last beach walk or visit the Butterfly Conservatory

Unwind with a morning stroll along the beach or revisit the butterfly garden for a peaceful start to your day.
USD16 or Free, 1h

10:30am

Check out and depart

Conclude your Key West trip and head to your next destination with fond memories.
Variable, N/A
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