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Highlights and Stories of Key West - Small Group Walking Tour

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Key West Highlights and Stories- 2020, 2021, 2022, and 2023 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.
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  • Professional, friendly, and highly trained local guide
  • Rain Ponchos are provided if it's raining
  • Full list of our favorite restaurant recommendations
  • Alcoholic beverages are usually available for purchase before, during, and after the tour
  • We suggest you bring at least one bottle of water
  • Hotel pickup and drop-off
  • Umbrellas if it is raining (rain ponchos are provided)
Departure Point

200 Greene St, Key West, FL 33040, USA 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.

Return Details

1400 Duval St, Key West, FL 33040, USA The tour ends at the Southernmost House Hotel, near the southernmost point of the continental United States.

  • Key West Museum of Art & History at the Custom House, Florida, United States
    Our tour starts outside the beautiful old Customs House building
  • Audubon House & Tropical Gardens, Florida, United States
    We'll stop outside the Geiger-Audubon house and discuss its unusual construction and the tremendous, legendary impact of the Geiger family on Key West history and fortunes.
    5 minutes
  • Harry S. Truman Little White House, Florida, United States
    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.
  • 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.
    5 minutes
  • 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.
    3 minutes
  • 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.
    3 minutes
  • 430 Duval St, Key West, FL 33040, Verenigde Staten
    We'll talk about the ghosts of the La Concha Hotel and the tragedies of its former rooftop bar.
  • US 1 Mile Marker 0, Florida, United States
    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 minutes
  • 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.
    5 minutes
  • Cornish Memorial AME Zion, Florida, United States
    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.
    3 minutes
  • 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.
  • The Ernest Hemingway Home and Museum, Florida, United States
    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.
    5 minutes
  • Key West Lighthouse and Keeper's Quarters Museum, Florida, United States
    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.
    5 minutes
  • 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.
    10 minutes
  • Southernmost Point, Florida, United States
    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.
    5 minutes
  • Wheelchair accessible
  • Infants and small children can ride in a pram or stroller
  • Service animals allowed
  • Public transportation options are available nearby
  • Not recommended for travelers with poor cardiovascular health
  • Travelers should have at least a moderate level of physical fitness
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
almamac2
10 Feb 2022
This tour was super interesting, we learned so much about the the history of Key West. Rich, our tour guide made it super fun with all his knowledge and personal stories, we laughed a lot and asked many questions. We are looking forward to do another tour with him. Rich we love you!.
G4770ZXshirleys
08 Feb 2022
This was an awesome walking tour and Richard was very personable and a great guide. He has lived in Key West all his life and is very knowledgeable about its history. We learned so much and it was all just very interesting. He was very open to questions and suggestions and had many anecdotal stories as well. He also had lots of good suggestions on places to eat and what their specialties were. If you want to get to know Key West, I highly recommend this tour.
jeffpavlak114
06 Feb 2022
The tour was very good. Our guide Rich is a third generation Key Wester (Conch). His knowledge of Key West history was incredible. I would highly recommend Rich.
This tour in Florida is organized by Hidden Key West Walking Tours

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We always double-check the availability with our local partners for each booking. Even though this is usually a swift process, it can take up to 24 hours. Once this process is completed you will receive your voucher or ticket by email. If our local partner is not able to confirm your booking we will offer you the best possible alternative. If the new date and/or time doesn’t fit your itinerary, we will reimburse the full amount paid.
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