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5 Days in Key West Florida Itinerary

Last updated: 2024 Jun 14

Exploring Historic Key West

Morning

Start your day with a visit to the iconic Ernest Hemingway Home and Museum. This historic site offers a glimpse into the life of one of America's most famous authors. Enjoy breakfast at Blue Heaven, known for its delicious breakfast options and unique atmosphere.

Afternoon

Head over to Duval Street for some shopping and sightseeing. This bustling street is the heart of Key West's social scene. For lunch, stop by Sloppy Joe's Bar, a historic bar that was once frequented by Ernest Hemingway himself.

Evening

End your day with a visit to Mallory Square to enjoy the famous sunset celebration. Street performers, local artisans, and food vendors create a festive atmosphere. Have dinner at El Meson de Pepe, which offers authentic Cuban cuisine.

Bedtime

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4.68
Ernest Hemingway Home and Museum
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4.83
Duval Street
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Nature and Maritime Adventures

Morning

Begin your day with a serene visit to the Key West Butterfly and Nature Conservatory. This beautiful conservatory is home to hundreds of butterflies and exotic birds. Enjoy breakfast at Banana Cafe, known for its delightful crepes.

Afternoon

Explore the underwater world with a dive at the Vandenberg Wreck. This artificial reef is a popular spot for divers. After your dive, have lunch at Conch Republic Seafood Company, offering fresh seafood dishes.

Evening

In the evening, embark on the relaxing Key West Windjammer Champagne Sunset Sail. Enjoy champagne as you watch the sun set over the ocean. For dinner, dine at Latitudes, located on Sunset Key with stunning views.

Bedtime

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4.94
Key West Butterfly and Nature Conservatory
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4.88
Vandenberg Wreck
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Cultural Immersion

Morning

Visit the historic Harry S. Truman Little White House, where President Truman spent his winters. Start your day with breakfast at Sarabeth's Key West, known for its hearty breakfasts.

Afternoon

Take a stroll through history at the Key West Cemetery, where you can see unique gravestones and learn about local legends. Have lunch at Garbo's Grill, famous for its food truck serving delicious tacos.

Evening

Experience some local culture with the entertaining and spooky Key West Southernmost Ghosts Haunted Walking Tour. End your evening with dinner at A&B Lobster House, offering fine dining in an elegant setting.

Bedtime

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4.67
Harry S. Truman Little White House
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4.64
Key West Cemetery
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Outdoor Fun and Relaxation

Morning

Start your day with an adventurous experience by parasailing at Smathers Beach with the Key West Parasailing at Smathers Beach. Grab breakfast before heading out from nearby cafe, Sandy's Cafe known for their Cuban coffee.

Afternoon

Relax on one of Key West’s most beautiful beaches: Smathers Beach. Spend time swimming or sunbathing before having lunch from Hogfish Bar & Grill known for their seafood dishes.

Evening

In evening take part in an exciting activity: Key West Schooner Sunset Sail with Food & Drinks and enjoy stunning views while savoring delicious snacks onboard . For dinner head towards The Flaming Buoy Filet Co for amazing steak options.

Bedtime

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4.83
Key West Parasailing at Smathers Beach
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4.76
Smathers Beach
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Final Day of Exploration

Morning

On your last day visit another historical site: Fort Zachary Taylor Historic State Park[12803] . After exploring enjoy breakfast from nearby cafe: Cuban Coffee Queen known for their Cuban sandwiches.

Afternoon

Spend afternoon visiting another iconic landmark: {Southernmost Point of Continental USA[2065]} . Have lunch from nearby restaurant: Blue Macaw Island Eats & Bar known tropical drinks.

Evening

End trip by taking part in cultural walking tour: { A- Key west Food Tasting Cultural Walking Tour[303118]} . For final dinner head towards restaurant : { R-Louie's Backyard } offering Caribbean-American cuisine.

Bedtime

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