Key West Florida 5-Day Adventure Itinerary

Begin your day with a visit to the serene Key West Garden Club. This beautiful garden is perfect for a peaceful morning stroll. Grab breakfast at The Cafe, A Mostly Vegetarian Place, offering healthy and delicious options.

In the afternoon, explore Fort Zachary Taylor Historic State Park (Fort Zachary Taylor). This park combines history with natural beauty and is ideal for both history buffs and nature lovers. Have lunch at Hogfish Bar & Grill, known for its fresh seafood and waterfront views.

Experience some local culture with an evening visit to Mallory Square. The square comes alive with street performers and vendors as you watch another beautiful sunset. For dinner, head to El Siboney Restaurant for authentic Cuban cuisine.

Kick off your day with an exciting adventure by taking part in the Key West Ultimate Parasailing Experience. Soar above the waters of Key West for breathtaking views. Enjoy breakfast at Garbo's Grill, famous for its creative food truck offerings.

After parasailing, visit the fascinating underwater world by snorkeling at Vandenberg Wreck (Vandenberg Wreck). Have lunch nearby at Alonzo's Oyster Bar , where you can savor fresh oysters and seafood dishes.

In the evening, join a ghost tour like the Key West Southernmost Ghosts Haunted Walking Tour. Discover spooky tales from Key West's past as you walk through historic streets. End your day with dinner at Santiago's Bodega, known for its tapas-style dishes.

Start your cultural immersion day with a visit to St. Paul's Episcopal Church (St. Paul's Key West Episcopal Church). The historic architecture is worth admiring in the morning light. Have breakfast at Bagatelle Island Restaurant offering classic American breakfasts in an elegant setting.

Spend your afternoon exploring more of Key West’s rich history by visiting Harry S. Truman Little White House (Harry S. Truman Little White House). Follow it up with lunch at Conch Republic Seafood Company which serves up delicious seafood right on the waterfront.

Conclude your cultural day by attending a local food tour such as the 3-hour guided walking tour (Key West Food Tasting and Cultural Walking Tour). You'll get to sample various local delicacies while learning about their origins. For dinner afterward head over to dessert heaven at  Better Than Sex - A Dessert Restaurant Key West.

Begin your final day in Key West with a visit to the Key West Butterfly and Nature Conservatory. This serene spot is perfect for a peaceful morning surrounded by beautiful butterflies. Enjoy breakfast at The Flaming Buoy Filet Co., known for its unique breakfast offerings and friendly atmosphere.

Spend your afternoon at Smathers Beach, one of Key West's most popular beaches. Relax on the sandy shores or take part in some water activities like kayaking or paddleboarding. For lunch, head to Louie's Backyard, offering delicious seafood with stunning ocean views.

End your trip with a memorable evening by taking part in the Key West Schooner Sunset Sail with Food & Drinks. This sail offers a perfect blend of relaxation and celebration as you enjoy food, drinks, and live music while watching the sunset. For dinner, dine at Little Pearl, known for its intimate setting and exquisite dishes.