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

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

2022 WINNER- Tripadvisor's Travelers' Choice Top 10 Tours in the USA!
2020, 2021, and 2022 WINNER- "Best Key West History Tour"

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

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 and story-filled look behind the scenes of historic Key West.

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

*Not recommended for people with impaired walking ability.

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, Naval Air Station 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

Informacion Adicional
"Confirmation will be received within 48 hours of booking, subject to availability"
"Not recommended for travelers with back problems"
"No heart problems or other serious medical conditions"
"Service animals allowed"
"Near public transportation"
"Stroller accessible"
"Wheelchair accessible"
"Travelers should have a moderate physical fitness level"
"This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund"
"This tour/activity will have a maximum of 12 travelers"
"Hand sanitizer available to travelers and staff"
"Social distancing enforced throughout experience"
"Guides required to regularly wash hands"
"Regular temperature checks for staff"

Duración: 2 Hours 15 Minutes
Lugar de comienzo: Mel Fisher Maritime Museum, 200 Greene St, Key West, FL 33040, USA

Cancelaciones y devoluciones: For a full refund, cancel at least 24 hours in advance of the start time of the experience.


  • Full list of our favorite restaurant recommendations
  • Professional, friendly, and highly trained local guide
  • Rain Ponchos are provided if it's raining

No Incluye

  • Hotel pickup and drop-off
  • Umbrellas if it is raining (rain ponchos are provided)
  • Alcoholic Beverages - Alcoholic beverages are usually available for purchase before, during, and after the tour
  • Bottled water - We suggest you bring at least one bottle of water


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