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5 Days of Relaxation and Activities in Key West Itinerary

Last updated: 2024 Jun 14

Exploring Historic Key West

Morning

Start your day with a visit to the Ernest Hemingway Home and Museum. This historic home offers a glimpse into the life of one of America's most iconic writers. The lush gardens and resident six-toed cats add to the charm.

Afternoon

Head over to Duval Street for some afternoon exploration. This bustling street is filled with shops, galleries, and cafes. For lunch, stop by Garbo's Grill for some delicious street food.

Evening

End your day at Mallory Square to witness the famous sunset celebration. Enjoy street performances and local crafts. For dinner, dine at A&B Lobster House for a seafood feast.

Bedtime

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Nature and Adventure

Morning

Begin your day with a peaceful visit to the Key West Butterfly and Nature Conservatory. Stroll through the lush environment filled with butterflies and exotic birds.

Afternoon

In the afternoon, head to Fort Zachary Taylor for some beach time and a bit of history. Enjoy swimming or snorkeling in the clear waters. Grab lunch at Hogfish Bar & Grill, known for its fresh seafood.

Evening

Take an evening sail on the Key West Schooner Sunset Sail with Food & Drinks. Enjoy breathtaking views of the sunset while sipping on drinks and savoring light bites.

Bedtime

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Cultural Immersion

Morning

Visit the beautiful Basilica of Saint Mary Star of the Sea in the morning. This serene church offers a moment of reflection amidst your travels.

Afternoon

Spend your afternoon exploring Key West Historic District. Wander through charming streets lined with historic homes. Have lunch at Blue Heaven, famous for its Caribbean-inspired dishes.

Evening

Join an evening tour like the Key West Ghosts of Key West Walking Tour. Discover spooky tales as you walk through haunted spots in Old Town Key West. For dinner, indulge in desserts at Better Than Sex - A Dessert Restaurant Key West.

Bedtime

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Aquatic Adventures

Morning

Kick off your day with an adventure by taking part in the Key West Ultimate Parasailing Experience. Soar above the crystal-clear waters for stunning views.

Afternoon

After parasailing, relax at Smathers Beach. Enjoy sunbathing or take a dip in the ocean. For lunch, visit El Siboney Restaurant for authentic Cuban cuisine.

Evening

Conclude your day with a unique experience on a tiki bar boat by booking the Key West 4-Hour Private Sandbar Cruise on a Tiki Bar Boat. Sip cocktails as you cruise around sandbars.

Bedtime

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Final Day of Relaxation and Farewell

Morning

Start your final day with a serene visit to the Key West Garden Club. This hidden gem offers beautiful gardens and a peaceful atmosphere, perfect for a relaxing morning stroll.

Afternoon

Spend your afternoon at the Key West Lighthouse and Keeper's Quarters Museum. Climb to the top for panoramic views of Key West. For lunch, head to Louie's Backyard, known for its stunning oceanfront views and delicious cuisine.

Evening

End your trip with a memorable evening at the Key West Windjammer Champagne Sunset Sail. Enjoy champagne and hors d'oeuvres as you sail into the sunset. For dinner, dine at Santiago's Bodega for a delightful tapas experience.

Bedtime

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