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

Key West Trip Overview

Historic Homes & Stories of Key West- 2020 and 2021 WINNER- “Best Key West History Tour”

Join our award-winning guides for a wonderful, fun, and informative 2 hour stroll through the celebrated Old Town neighborhoods where you’ll discover many of the most beautiful, historic homes and unique architectural landmarks that have contributed so significantly to the history, culture, and legends of our remarkable island community.

We’ll see the exteriors of a variety of beautiful homes and public buildings, each with its own legendary story, notable history, and rich style. There’s something for everyone to enjoy on this fascinating look behind the scenes of historic Key West.

*Voted Top Tour Guides of North America
*Over 20 years experience
*Our guides have been featured in many leading publications including Gentry, Conde Nast, Frommer’s Travel Guide, Jetset, Hamptons, Travel Weekly, Private Islands, and USA Today.

We look forward to sharing the history of Old Town Key West with you.

Additional Info

Duration: 2 hours
Starts: Key West, United States
Trip Category: Cultural & Theme Tours >> Cultural Tours



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What to Expect When Visiting Key West, Florida, United States

Historic Homes & Stories of Key West- 2020 and 2021 WINNER- “Best Key West History Tour”

Join our award-winning guides for a wonderful, fun, and informative 2 hour stroll through the celebrated Old Town neighborhoods where you’ll discover many of the most beautiful, historic homes and unique architectural landmarks that have contributed so significantly to the history, culture, and legends of our remarkable island community.

We’ll see the exteriors of a variety of beautiful homes and public buildings, each with its own legendary story, notable history, and rich style. There’s something for everyone to enjoy on this fascinating look behind the scenes of historic Key West.

*Voted Top Tour Guides of North America
*Over 20 years experience
*Our guides have been featured in many leading publications including Gentry, Conde Nast, Frommer’s Travel Guide, Jetset, Hamptons, Travel Weekly, Private Islands, and USA Today.

We look forward to sharing the history of Old Town Key West with you.

Itinerary
This is a typical itinerary for this product

Pass By: Audubon House & Tropical Gardens, 205 Whitehead St, Key West, FL 33040-6522

We’ll begin our tour outside the beautiful Geiger-Audubon Home and discuss its unique design features, gardens, and how it started the historic restoration efforts for all of Old Town Key West.

Pass By: Key West Museum of Art & History at the Custom House, 281 Front St, Key West, FL 33040-8313

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.

Stop At: 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 visit the beautiful Presidential Gates.

Duration: 5 minutes

Pass By: Harry S. Truman Little White House, 111 Front St, Key West, FL 33040-8311

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.

Stop At: First Flight Island Restaurant & Brewery, 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.

Duration: 3 minutes

Stop At: Captain George Carey House, 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.

Duration: 5 minutes

Stop At: 429 Caroline St, Naval Air Station 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.

Duration: 5 minutes

Stop At: Curry Mansion Inn, 511 Caroline St, Key West, FL 33040-6604

We’ll stop outside to view the Victorian splendor of the Curry 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.

Duration: 5 minutes

Stop At: Casa Antigua, 314 Simonton St, Key West, FL 33040, USA

We’ll pass by Casa Antigua and talk about its unusual origins, its history with Ernest Hemingway, and the famous book he authored there.

Duration: 5 minutes

Stop At: The Artist House, 534 Eaton St, Key West, FL 33040, USA

We’ll view the magnificent Queen Anne style of the Otto-Artist House and reveal the sinister history of its most infamous occupant.

Duration: 5 minutes

Stop At: Richard Peacon House, 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, its famous owners, and the stir it caused when it sold in 1981.

Duration: 5 minutes

Stop At: The Freeman-Curry House, 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.

Duration: 5 minutes



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