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Key West Historic Homes and Island History - Small Group Walking Tour

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Historic Homes & Island History of Key West- 2020, 2021, 2022, and 2023 WINNER- "Best Key West History Tour" TripAdvisor ranked top 10 history tours in North America. Join our award-winning guides for a wonderful, fun, and informative 2.25 hour stroll through the fantastic Old Town neighborhoods and discover the history and many beautiful homes and unique architectural landmarks that have contributed significantly to the culture and legends of our remarkable island community. We’ll see the exteriors of a variety of beautiful homes and public buildings (we do not go inside), each with its own legendary story, notable history, and rich style. There's something for everyone to enjoy on this fascinating and story-filled look behind the scenes of historic Key West. *Our guides have been featured in leading publications including Conde Nast, Frommer’s, Jetset, Hamptons, Travel Weekly, Private Islands, and USA Today. *Not recommended for people with impaired walking ability.
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  • Professional, friendly, and highly trained local guide
  • Rain Ponchos are provided if it's raining
  • Full list of our favorite restaurant recommendations
  • Hotel pickup and drop-off
  • Umbrellas if it is raining (rain ponchos are provided)
  • Alcoholic beverages are usually available for purchase before, during, and after the tour
  • We suggest you bring at least one bottle of water
Departure Point

200 Greene St, Key West, FL 33040, USA The meeting point for the start of the tour is the sidewalk at 200 Greene Street in front of the Mel Fisher Museum Building and directly across from the Opal Key Resort entrance sign. This is slightly southwest on Greene Street just past the corner of Greene Street and Whitehead Street.

Return Details

730 Eaton St, Key West, FL 33040, USA The tour ends at the Captain John Bartlum House- 730 Eaton Street, Key West, FL

  • Audubon House & Tropical Gardens, Florida, United States
    We'll begin our tour outside the beautiful Geiger-Audubon Home and discuss its unique design features, the fascinating history of the Geiger family, the stories of "Wrecking" in Key West, and how this home started the historic restoration efforts for all of Old Town Key West.
    5 minutes
  • Key West Museum of Art & History at the Custom House, Florida, United States
    We'll pass by the stunning Old Customs House. We will discuss why it was constructed of brick, the many fascinating design anomalies it contains since the designers never visited Key West, and the restoration efforts that have turned it into a fantastic museum.
    5 minutes
  • Truman Annex Park, Key West, FL 33040, USA
    We'll stroll into the beautiful Truman Annex Neighborhood, talk about the important history it played as a military base and stopping piracy offshore. How the base prospered and floundered and how it has been renovated into of the most sought after property developments in America. We will also stop to visit and discuss the beautiful Presidential Gates.
    5 minutes
  • Harry S. Truman Little White House, Florida, United States
    We'll walk past the Truman Little White House and learn about President Truman's time in Key West and the historic events surrounding his Key West White House.
    5 minutes
  • 301 Whitehead St, Key West, FL 33040, USA
    We'll see the original Pan American Airlines office and learn about the birth of international aviation in the United States. We will stop outside the building for an opportunity to take photos and for your guide to share stories and the history of the location. We will not be going inside the building.
    3 minutes
  • 410 Caroline St, Key West, FL 33040, USA
    We'll stop at the Captain George Carey- Jesse Porter- Robert Frost house to discuss its unique history, unusual color scheme, and the many celebrities who have been entertained there over the years. We will also discuss Robert Frost living in Key West and his friendship with Miss Jesse.
    5 minutes
  • 429 Caroline St, Key West, FL 33040, USA
    We'll stop to admire the grandeur of the Dr. Joseph Yates Porter Mansion and discuss the role Dr. Porter and the mansion played in eradicating Yellow Fever in Florida.
    5 minutes
  • Curry Mansion Inn, Florida, United States
    We'll stop outside to view the Victorian splendor of the Curry-Amsterdam Mansion, discuss this family's incredible legacy of seven mansions in Key West, and the historic events that took place in the home's original kitchen as well as the legendary stories of Edith Amsterdam - the true Grand Dame of Key West.
    5 minutes
  • 314 Simonton St, Key West, FL 33040, Verenigde Staten
    We'll pass by Casa Antigua and talk about its unusual origins, its history with Ernest Hemingway, and the famous book he authored there.
    5 minutes
  • 620 Eaton St, Key West, FL 33040, USA
    We will view the beautiful George Henry Curry Mansion- noted for its magnificent styling, wrap-around veranda, and other unique features.
    5 minutes
  • 712 Eaton St, Key West, FL 33040, USA
    We'll stop to see the stunning beauty of the unique "Octagonal House" and learn about its history, design features, its famous owners, and the upheaval it caused to the housing market in Key West when it sold in 1981.
    5 minutes
  • 724 Eaton St, Key West, FL 33040, USA
    We'll pass by the unique beauty of the Freeman-Curry Mansion, learn about it being moved, and how it has only been sold once in over 155 years.
    5 minutes
  • 630 Eaton St, Key West, FL 33040, USA
    We will wrap up the tour with a discussion about "the Conch Republic" and a look at John Bartlum's Bahama House with its unique age and how John Bartlum was able to "build" the house.
    10 minutes
  • Not recommended for travelers with spinal injuries
  • Not recommended for travelers with poor cardiovascular health
  • Service animals allowed
  • Public transportation options are available nearby
  • Infants and small children can ride in a pram or stroller
  • Wheelchair accessible
  • Travelers should have at least a moderate level of physical fitness
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
johnsU7981QU
12 May 2023
Great guide with lots of local stories and knowledge about the history and architecture of the homes. Provides a great understanding of the history of Key West and the crazy people that founded it.
California_J-nice5
05 May 2023
Easily booked, easily met up, and enjoyed immensely this great tour sharing the history of Key West focused on its architecture. Richard gives terrific history with fun facts while giving consideration to the tour group's endurance and size. Highly reccommend!
Mooney_L
04 May 2023
Had such an amazing tour. Very informative. Learned a lot of information about Key West’s history. I would do it again for sure.
This tour in Florida is organized by Hidden Key West Walking Tours

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