Key West Trip Overview
Key West Highlights and Stories Private Tour- “2020 and 2021 WINNER “Best Key West Walking Tour”
Join Key West’s unofficial “mayor” on a wonderful 2.5 hour private stroll through the historic Old Town streets. Our goal is for you to have fun while enjoying the rich and colorful history, legends, points of interest, and culture that make Old Town Key West unique and famous across the globe. The quality of our tours and our guides is unmatched on the island. With unique insights and carefully crafted tour routes, we strive to provide the best walking tours available in Key West.
*Consistently ranked as the top “Highlights Tour” by Keys Tourism Association
*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 Old Town Key West with you.
Additional Info
Duration: 2 hours 15 minutes
Starts: Key West, United States
Trip Category: Cultural & Theme Tours >> Cultural Tours
Explore Key West Promoted Experiences
What to Expect When Visiting Key West, Florida, United States
Key West Highlights and Stories Private Tour- “2020 and 2021 WINNER “Best Key West Walking Tour”
Join Key West’s unofficial “mayor” on a wonderful 2.5 hour private stroll through the historic Old Town streets. Our goal is for you to have fun while enjoying the rich and colorful history, legends, points of interest, and culture that make Old Town Key West unique and famous across the globe. The quality of our tours and our guides is unmatched on the island. With unique insights and carefully crafted tour routes, we strive to provide the best walking tours available in Key West.
*Consistently ranked as the top “Highlights Tour” by Keys Tourism Association
*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 Old Town Key West with you.
Itinerary
This is a typical itinerary for this product
Pass By: Key West Museum of Art & History at the Custom House, 281 Front St, Key West, FL 33040-8313
Our tour starts outside the beautiful old Customs House building
Stop At: Audubon House & Tropical Gardens, 205 Whitehead St, Key West, FL 33040-6522
We’ll stop outside the Geiger-Audubon house and discuss its unusual construction and the tremendous, legendary impact of the Geiger family and John Audubon on Key West history and fortunes.
Duration: 5 minutes
Pass By: Harry S. Truman Little White House, 111 Front St, Key West, FL 33040-8311
We will 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: 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
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: The Banyan Resort, 323 Whitehead St, Key West, FL 33040, USA
We’ll visit the largest Banyan Tree in Key West and learn about the unusual characteristics of these remarkable giants. We will stop for an opportunity to take photos and for your guide to share stories and the history of the location and the tree. We will not be going inside the resort.
Duration: 3 minutes
Pass By: Crowne Plaza Key West-La Concha, an IHG Hotel, 430 Duval St, Naval Air Station Key West, FL 33040, USA
We’ll talk about the ghosts of the La Concha Hotel and the tragedies of its former rooftop bar.
Stop At: Monroe County Courthouse, 302 Fleming St, Key West, FL 33040, USA
We’ll see the beautiful Monroe County Courthouse, visit the magnificent Kapok Tree, and learn about the Great Fire of 1886 that wiped out Key West for the second time. We will stop outside the courthouse and tree 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 courthouse.
Duration: 5 minutes
Stop At: US 1 Mile Marker 0, 490 Whitehead St, Key West, FL 33040-6545
We’ll stop for photos at the famous Mile Marker 0 – marking the beginning/end of Highway 1 which stretches 2,369 miles to Fort Kent, Maine. Your guide will share stories and the history of the location.
Duration: 5 minutes
Pass By: Petronia Street, Petronia St, Key West, FL 33040, USA
We’ll walk through the Old Bahama Village and learn its history. Then, we make our way down Petronia Street with its wonderful local restaurants and our top recommendations including the famous Blue Heaven where you’ll find the island’s best Key Lime pie. Then, we’ll stroll past rows of “conch” style homes and learn about the features of these home, the unique aspects of their history and construction, and how the word “conch” became synonymous with Key West.
Stop At: Cornish Memorial AME Zion, 702 Whitehead St, Key West, FL 33040-7420
We will discuss the history of freed slave, Sandy Cornish and the Cornish AME Zion Church’s role in Key West’s history. We will have time for photos outside the church. We will not be going inside the building.
Duration: 3 minutes
Stop At: The Ernest Hemingway Home and Museum, 907 Whitehead Street, Key West, FL 33040-7473
We’ll stroll by the Ernest Hemingway House and discuss some of the history and legends of the home and Hemingway’s time in Key West. We will stop outside the property for an opportunity to take photos from a distance. We will not be going inside the property.
Duration: 5 minutes
Stop At: Key West Lighthouse and Keeper’s Quarters Museum, 938 Whitehead St, Key West, FL 33040-7423
We’ll walk to the Key West Lighthouse and learn about its history, its original location, and its role in the Great Havana Hurricane of 1846 that wiped out Key West for the first time. We will stop outside the lighthouse grounds for an opportunity to take photos. We will not be going inside the grounds.
Duration: 5 minutes
Stop At: The Southernmost House Hotel, 1400 Duval St, Key West, FL 33040, USA
We’ll visit the beautiful Southernmost House Hotel and learn about its rich role in our history and the many celebrities and dignitaries who have visited this beautiful spot. Here we will conclude our tour with questions and time for a cocktail or snack.
Duration: 10 minutes
Stop At: Southernmost Point, Whitehead Street, Key West, FL 33040
We’ll see the Southernmost Point Buoy- marking the southernmost point of the Continental USA. We will stop to take photos and to discuss the history and other interesting features of the location.
Duration: 5 minutes
