What You Will Do
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.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Itinerary
Meeting Point
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.
1
Audubon House & Tropical Gardens
5 minutes
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.
2
Key West Museum of Art & History at the Custom House
5 minutes
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.
3
Truman Annex Park
5 minutes
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.
4
Truman Little White House
5 minutes
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
First Flight Island Restaurant & Brewery
3 minutes
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.
6
Captain George Carey House
5 minutes
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.
7
429 Caroline St
5 minutes
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.
8
Curry Mansion Inn
5 minutes
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.
9
Casa Antigua
5 minutes
We'll pass by Casa Antigua and talk about its unusual origins, its history with Ernest Hemingway, and the famous book he authored there.
10
620 Eaton St
5 minutes
We will view the beautiful George Henry Curry Mansion- noted for its magnificent styling, wrap-around veranda, and other unique features.
11
Richard Peacon House
5 minutes
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.
12
The Freeman-Curry House
5 minutes
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.
13
630 Eaton St
10 minutes
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.
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