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5-Day Key West Escape: Arrival, Beaches, History & Island Charm

Viewed by 58 travelers

Day 1: Arrival and Dinner

Key West, Florida on September 4, 2025

7:00pm

Arrival in Key West and check-in

Settle into your accommodation and get ready to explore the island starting with a delicious dinner.
Variable, 1h

7:30pm

Dinner at Blue Heaven

Enjoy dinner at the iconic Blue Heaven featuring island-inspired dishes in a colorful outdoor garden setting.
USD40, 1h30m

9:00pm

Evening stroll along Duval Street

Take a relaxing walk along the lively Duval Street to experience Key West nightlife and vibrant atmosphere.
Free, 1h
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Day 2: Old Town and Museums

Key West, Florida on September 5, 2025

8:00am

Breakfast at Sarabeth's Key West

Start your day with classic American breakfast favorites and fresh juices at Sarabeth's.
USD18, 1h

9:30am

Stroll through Old Town Key West

Explore the charming streets filled with historic homes, galleries, and shops that showcase local art and culture.
Free, 2h

12:00pm

Lunch at El Siboney

Enjoy authentic Cuban cuisine and generous portions at this beloved local favorite.
USD15, 1h

1:30pm

Ernest Hemingway Home and Museum

Tour the famous residence of Ernest Hemingway, surrounded by lush gardens and six-toed cats.
USD17, 1h30m

3:30pm

Key West Lighthouse and Keeper’s Quarters Museum

Climb the lighthouse for panoramic views and explore maritime history in the keeper’s quarters.
USD12, 1h

5:00pm

Relax at Mallory Square

Experience the vibrant sunset celebration with street performers, local artists, and a festive atmosphere.
Free, 2h

7:30pm

Dinner at Latitudes

Savor gourmet seafood and island-inspired dishes with breathtaking views from Sunset Key; advance reservations recommended.
USD55, 2h
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Day 3: Beaches & Water Fun

Key West, Florida on September 6, 2025

8:00am

Breakfast at Cuban Coffee Queen

Fuel your morning with strong Cuban coffee and delicious breakfast sandwiches.
USD8, 30m

9:00am

Fort Zachary Taylor Historic State Park

Spend the morning soaking up sun, swimming, or exploring the historic Civil War fort at this prime beach.
USD6, 3h

12:30pm

Lunch at Salute! On The Beach

Dine on fresh seafood and island cocktails just steps from the sand in a casual beachside setting.
USD25, 1h

2:00pm

Snorkeling Tour

Discover the vibrant coral reefs and sea life on a guided 3-hour snorkeling adventure departing near the Key West Shipwreck Museum.
USD70, 3h

6:00pm

Sunset Sail

Relax aboard a sailing cruise along the coast as you watch a spectacular Key West sunset.
USD60, 2h

8:30pm

Dinner at The Flaming Buoy Filet Co.

Enjoy inventive American cuisine with island flair in a cozy and welcoming atmosphere.
USD40, 2h
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Day 4: Nature & Outdoor Adventures

Key West, Florida on September 7, 2025

7:30am

Breakfast at Cuban Coffee Queen

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

8:00am

Kayaking and Eco Tour at Great White Heron National Wildlife Refuge

Explore mangrove forests and observe coastal wildlife on this 4-hour guided kayaking tour.
USD80, 4h

12:30pm

Lunch at Banana Cafe

Relax with French-inspired cuisine in a cozy setting, perfect after an active morning.
USD30, 1h

2:00pm

Higgs Beach

Unwind by swimming or sunbathing at this calm, family-friendly beach with picnic facilities.
Free, 2h

4:30pm

Eco-Discovery Center Visit

Learn about the Florida Keys ecosystem through interactive exhibits and educational displays.
Free, 1h

6:00pm

Sunset at Sunset Pier

Enjoy the lively atmosphere, live music, and beautiful sunset views from this waterfront hotspot.
Free, 1h30m

8:00pm

Dinner at Louie's Backyard

Dine on gourmet seafood and seasonal fare in an elegant oceanside setting.
USD50, 2h
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Day 5: Leisure & Departure

Key West, Florida on September 8, 2025

8:00am

Breakfast at Cuban Coffee Queen

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

9:00am

Leisurely beach walk or Butterfly Conservatory visit

Choose between a peaceful morning walk along the beach or a serene visit to the Key West Butterfly and Nature Conservatory.
USD16 or Free, 1h

10:30am

Packing and Check-out

Finalize packing and prepare for your departure from Key West.
Variable, N/A
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