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Private Highlights and Stories of Key West Walking Tour

Overview
Key West Highlights and Stories Private Tour- “2020 and 2021 WINNER "Best Key West Walking Tour"

Join our award-winning guides for a wonderful, fun, and informative 2.5 hour walk through the historic streets of Old Town Key West. Our goal is for you to have a fantastic time as we bring to life the rich and colorful history, legends, points of interest, flora/fauna, and culture that make Old Town Key West unique and famous across the globe.

There's something for everyone to enjoy on this fascinating and story-filled look behind the scenes of historic Key West.

*Consistently ranked as the top “Highlights Tour” by Keys Tourism Association
*Voted Top Tour Guides of North America
*20+ 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.

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

*Not recommended for people with impaired walking ability.
City: Key West
Sun 23 Feb
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You can choose the date already on the booking website
Starting at $185.00
Sun 23 Feb
Starting at $185.00
Make a reservation
What's Included
Professional, friendly, and highly trained local guide
Rain Ponchos are provided if it's raining
Full list of our favorite restaurant recommendations
Additional Info
  • 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
  • Hand sanitiser available to travellers and staff
  • Guides required to regularly wash hands
  • Regular temperature checks for staff
What To Expect
1
Key West Museum of Art & History at the Custom House
Our tour starts outside the beautiful old Customs House building
2
Audubon House & Tropical Gardens
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.
3
Harry S. Truman Little White House
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.
4
US 1 Mile Marker 0
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.
5
Cornish Memorial AME Zion
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.
6
The Ernest Hemingway Home and Museum
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.
7
Key West Lighthouse and Keeper's Quarters Museum
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.
8
Southernmost Point
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.
Show 5 more stops
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews (7)
Keywestmichael
Jan 2022
This is the gold standard of walking tours of Key West. In fact, it is the gold standard of any tour of Key West and is the best way for any visitor who arrives on this island to see the historic city. Richard’s passion for Key West and personal knowledge of the island makes the tour unique and special. I have taken tours of Key West by train, trolley, boat and car and none of the tours provided the personal experience that Richard provides as a tour guide. If I could give this tour more than five stars I would. If you are coming to Key West for vacation, book this tour first.
Response from Host
Jan 2022
We are so pleased you enjoyed the tour. Thank you for taking the time to provide a review for us. We look forward to seeing you again in Key West soon!
Raychel1995
Dec 2021
A truly unique and worthwhile experience! With his family’s roots in Key West dating back for many years, Richard offered a thoughtful and highly informative tour with some great personal insights and recommendations. It felt more intimate and less ‘touristy’ compared to other larger tours. It is a great activity if you’re interested in learning more about Key West’s history and receiving recommendations on spots to eat well and have fun on your trip!
Response from Host
Jan 2022
We are glad you enjoyed the tour. Thank you for joining us.
Kara_D
Apr 2021
Richard was a fantastic story teller and even kept the attention of our two teenagers! It was the perfect amount of time, history and facts. The distance walking was very doable too.
Response from Host
Apr 2021
We are glad you enjoyed the tour. We are fortunate to have the very best guides in Key West, and we are pleased to hear how much you enjoyed your time with Richard.

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