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Historic Homes and History of Key West

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

  • 2 hr 15 min
  • 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 History Tour! Top 10 History Tours in the United States (Tripadvisor/Viator ranking) Join Key West's unofficial "mayor" as we take you on a wonderful 2.25 hour walk through the historic Old Town neighborhoods where you'll discover many of the beautiful, historic homes and unique architectural landmarks that have contributed significantly to the history, culture, and legends of our celebrated island community. We’ll learn about Key West's fascinating history while seeing the exteriors of a variety of homes and buildings (we do not go inside), each with its own story, notable history, and rich style. We'll talk about the early family mansions of Old Town, the influence of the Bahamas on our architecture and why we have "Bahama Houses", the boom and bust days for our Key West, how the island's historic preservation work started, the lasting impacts of the 1846 Hurricane and Great Fire of 1886, why we have "eyebrow" houses, the superstitions reflected in certain design features, and the unique, but necessary, architectural elements used to combat heat, termites, and hurricanes. We start at the beautiful, old Customs House. From there, we make our way ¾ of a mile into the heart of historic Old Town Key West. We’ll stroll by and discuss the Geiger-Audubon House, Truman's Little White House, the Presidential Gates, Pan American Airline’s first office, the Captain George Carey Home (aka Jesse Porter Heritage House and Robert Frost Cottage), Dr. Joseph Yates Porter home (pivotal in the yellow fever epidemic), the stunning Curry-Amsterdam Mansion, Casa Antigua (Hemingway’s first Key West residence where he penned A Farewell to Arms), the Eyebrow House, the art-deco triumph of the old Masonic Temple, the stunning octagonal design of the Richard Peacon (aka Calvin Klein) House, the magnificent Freeman-Curry Mansion, and John Bartlum's Bahama Home. At that point the tour ends, but our guide will be happy to escort guests to the lively marina area where they can shop for souvenirs, grab a drink, or enjoy a meal. Please remember this tour includes walking at a moderate pace for .75 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

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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