4-Day Ultimate Key West Adventure Itinerary

Day 1: Arrive and Explore

Key West, Florida

8:00 AM

Breakfast at Blue Heaven

Start your adventure right with a delicious breakfast at Blue Heaven, famous for its outdoor seating and the best pancakes in town.
Located just 0.5 miles from downtown, easily accessible by a 10-minute walk.
USD15, 1 hour

9:30 AM

Visit Ernest Hemingway Home and Museum

Discover the home of the legendary writer Ernest Hemingway, where he lived during the 1930s, surrounded by tropical gardens.
Just a 15-minute walk from Blue Heaven.
USD15, 1.5 hours

11:00 AM

Explore Key West Butterfly & Nature Conservatory

Step into a magical world filled with hundreds of butterflies flying freely amid beautiful flora in this serene conservatory.
A 10-minute stroll from Hemingway's house.
USD15, 1 hour

12:30 PM

Lunch at El Meson de Pepe

Savor a delightful Cuban meal and refreshing mojito at this lively, vibrant eatery filled with local flavor.
Only a 15-minute walk from the conservatory.
USD20, 1.5 hours

2:00 PM

Visit Mallory Square

Spend your afternoon enjoying the vibrant atmosphere, local shops, and street performers at this iconic square.
A quick 5-minute walk from El Meson de Pepe.
Free, 2 hours

4:00 PM

Go on a Sunset Sail

Board a sailboat for a breathtaking sunset cruise, soaking in the stunning views of the Key West coastline.
Departure point is a 10-minute walk from Mallory Square.
USD75, 2 hours

7:00 PM

Dinner at The Conch Shack

Indulge in fresh seafood served in a casual beachside setting, known for its conch fritters and local catch of the day.
10-minute walk from the sailboat drop-off point.
USD30, 1.5 hours
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Day 2: Adventure Day

Key West, Florida

8:00 AM

Breakfast at Wieland's

Start your day with a hearty breakfast at Wieland's featuring homemade pastries and farm-fresh eggs.
Just a 5-minute walk from downtown.
USD10, 1 hour

9:00 AM

Snorkeling at Dry Tortugas National Park

Embark on a ferry ride to Dry Tortugas to explore stunning coral reefs and abundant marine life.
Note: 30-minute drive to ferry terminal, followed by a 2-hour boat ride.
USD190, 6 hours

3:00 PM

Return and Relax at Fort Zachary Taylor

Unwind at this beautiful state park, swim in the calm waters, and explore the historic fort.
15-minute ride from the ferry dock.
USD7, 2 hours

6:00 PM

Dinner at Louie's Backyard

Treat yourself to a romantic dinner on the beach with an exquisite view, known for its fresh seafood and tropical cocktails.
A 10-minute walk from Fort Zachary Taylor.
USD50, 2 hours
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Day 3: Cultural Immersion

Key West, Florida

8:00 AM

Breakfast at Sarabeth's

Enjoy a sophisticated breakfast with options ranging from fruit pancakes to egg dishes. Perfect for fuel before a busy day.
Walking distance of about 0.5 miles from downtown.
USD20, 1 hour

9:30 AM

Visit the Key West Lighthouse

Climb to the top of this historic lighthouse for amazing views of the island and the surrounding waters.
Just a 10-minute walk from Sarabeth's.
USD10, 1 hour

11:00 AM

Explore the Key West Museum of Art & History

Discover the island's rich culture and history through exhibits that showcase local artists and historical artifacts.
Located 0.5 miles away, about a 10-minute walk.
USD10, 1.5 hours

12:30 PM

Lunch at A&B Lobster House

Indulge in succulent lobster dishes and other seafood in a charming harbor setting.
A 15-minute walk from the museum.
USD40, 1.5 hours

2:00 PM

Visit the Southernmost Point Buoy

Stop by this iconic landmark for a photo opportunity at the southernmost point in the continental U.S.
An easy 15-minute walk from A&B Lobster House.
Free, 30 minutes

3:00 PM

Key West Art District

Stroll through the vibrant Art District filled with unique galleries, boutiques, and local artists’ exhibits.
A short 5-minute walk from the Southernmost Point Buoy.
Free, 2 hours

5:00 PM

Dinner at Sunset Pier

Dine on fresh seafood while enjoying the sunset views and lively atmosphere at this popular pier restaurant.
A 20-minute walk from the Art District.
USD35, 2 hours
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Day 4: Relaxation and Reflection

Key West, Florida

8:00 AM

Breakfast at The Bagel Factory

Grab a quick breakfast with fresh bagels and coffee to energize for your last day of adventure.
Just a 10-minute walk from downtown.
USD8, 1 hour

9:00 AM

Kayaking the Mangroves

Paddle through the stunning mangroves of Key West, experiencing the breathtaking natural beauty and wildlife.
Kayak rentals available at several shops; head to nearby location within 0.5 miles.
USD50, 2 hours

11:30 AM

Relax at Higgs Beach

Spend some time soaking up the sun at Higgs Beach, with a peaceful atmosphere and beautiful scenery.
Just a 15-minute walk from the kayak rental location.
Free, 2 hours

1:30 PM

Lunch at Fort Zachary Taylor's Snack Bar

Enjoy a casual lunch with sandwiches and snacks right by the beach.
In the same park as Higgs Beach, a short walk away.
USD15, 1 hour

2:30 PM

Visit the Audubon House & Tropical Gardens

Explore the beautiful gardens and historic house where naturalist John James Audubon lived and painted.
Just a 10-minute walk from the snack bar.
USD12, 1.5 hours

4:00 PM

Final sunset at Mallory Square

Conclude your Key West adventure with a sunset viewing at Mallory Square, surrounded by street performances and a lively ambiance.
In the same area as previous visits, easily walkable.
Free, 1.5 hours

6:00 PM

Dinner at The Key West Grill

Wrap up your trip with a relaxed dinner at The Key West Grill, enjoying classic American dishes with a Caribbean twist.
A 15-minute walk from Mallory Square.
USD30, 1.5 hours
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