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The Highlights and Stories of Key West

2.5 Hour Walking Tour- 10am & 1:30pm (see below for tour details)

  • 49 US dollars
  • Tour meets on the sidewalk at 200 Greene St. in front of the Mel Fisher Museum

Service Description

2020, 2021, 2022 and 2023 Winner- Best Key West Walking Tour! Join Key West’s unofficial “mayor” as we take you on a wonderful 2.5 hour walk through the historic Old Town streets where you’ll discover many of the highlights and secrets of the history, culture, legends, and points of interest of our remarkable island community. We start in front of the beautiful, old Customs House and make our way south 1.25 miles to the historic “Southernmost House Hotel” mansion. Along the way we’ll talk about the fascinating history of Key West, the boom days and the bust days, its people throughout the years, the rich traditions in the architecture of our buildings, the legends passed down through the generations, the unique flora and fauna found on our island, our most famous ghosts, the food that has shaped our culture, the many celebrities and characters that have graced our community, and the stories behind why we call ourselves the Conch Republic. We’ll get off the crowded tourist track and into the quieter streets to stroll by and learn about Truman’s Little White House, the beautiful Truman Annex neighborhood, the original Pan American Airlines office, the island’s largest and most famous Banyan Tree, Mile Marker 0, the historic courthouse with its magnificent Kapok tree, the unique restaurants of Petronia Street, the old Bahama Village neighborhood, rows of original conch houses, the Hemingway House, the old Lighthouse, the Southernmost Buoy (marking the southernmost point of the continental United States), the Gato Family home, and the stunning Victorian beauty of the “Southernmost House Hotel” mansion where the tour will end. There will be time for a cocktail or cool beverage at the mansion before you head back up Duval Street to explore its shops, bars, and restaurants on your own. We look forward to sharing Old Town Key West with you in this “Highlights of Key West Tour”. Please remember this tour includes walking at a moderate pace for 1.25 miles. You should have a moderate level of fitness and be able to proceed at a moderate pace. Tours can easily be modified to accommodate wheelchairs. However, this tour is not recommended for people with impaired walking ability unless they are using a wheelchair or motorized scooter. Private tours are also available- ask us for details.

Upcoming Sessions

Cancellation Policy

Customers will receive a full refund via their original method of payment if cancellation is made by you (and confirmed back by us) 24 hours or more prior to the starting time of the tour you booked. Any cancellation made by the customer within 24 hours of the tour start time will not be eligible for a refund. Naturally, customers will receive a full refund in case of operator cancellation due to weather or other unforeseen circumstances. Contact us by phone at 305-809-6170 or email to cancel or to inquire about a possible cancellation. No-shows will be charged the full price. Please note that private tours or corporate events are subject to different cancellation policies. We are unable to delay the start of the tours if you are running late. We are not responsible for traffic related delays. We will attempt to rebook you on the next available tour if you wish. If unable to, then our cancellation policy above will take effect.

Contact Details


Key West, Florida, USA

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