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.
What's Included
Full list of our favorite restaurant recommendations
Professional, friendly, and highly trained local guide
Rain Ponchos are provided if it's raining
What's Not Included
Alcoholic beverages are usually available for purchase before, during, and after the tour
Hotel pickup and drop-off
Umbrellas if it is raining (rain ponchos are provided)
We suggest you bring at least one bottle of water
Traveler Information
ADULT: Age: 10 - 110
Additional Info
Hand sanitiser available to travellers and staff
Not recommended for travelers with poor cardiovascular health
Public transportation options are available nearby
Service animals allowed
Travelers should have at least a moderate level of physical fitness
Hand sanitiser available to travellers and staff
Not recommended for travelers with poor cardiovascular health
Public transportation options are available nearby
Service animals allowed
Travelers should have at least a moderate level of physical fitness
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, you must cancel at least 24 hours before the experience’s start time.
If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
What To Expect
Audubon House & Tropical Gardens
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.
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Admission Ticket Free
Key West Museum of Art & History at the Custom House
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.
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Admission Ticket Free
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
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Admission Ticket Free
Harry S. Truman Little White House
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.
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Admission Ticket Free
Curry Mansion Inn
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.
5 minutes
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Admission Ticket Free
Reviews
Key West past and present
emily1954, 08-12-2022
Richard, our tour guide was excellent, very profession with a lot fun stories about Key West past and present. He shared his own stories about his childhood and family. Some stories was sad, some fun, but every one of them was very inspire.
Fantastically informative tour
P2094WPerics, 08-12-2022
I have done many of these over the years, but Robert is about the best tour guide I have ever experienced. Native to Key West, he brings encyclopedic knowledge about the town’s history, inhabitants and architecture. By the end I had acquired a completely different understanding of the place. He is respectful of the needs of his guests, packs an enormous amount of information into his chats, and is meticulously on time. I would give him 7 stars if I could.
Richard the Excellent Guide
Wanderer52682294299, 07-12-2022
Our Guide Richard, a Key West native was extremely knowledgeable and a terrific guide.
He explained in detail every home and places in between that we visited. We’ve been coming to Key West for 27 years and gained so much historical knowledge from Richard. Definitely was a highlight of our visit this year.
Don't miss this walking tour
TheGoBird, 27-11-2022
Richard makes an excellent guide. Evidently he has lived on the island his whole life. He prides himself on local knowledge to the point of telling you when a local sign or plague is incorrect. I like their policy of keeping the groups small.
Learn through the fun
Nchorna, 26-11-2022
It wonderful walk with very interesting and knowledgeable tour guide Richard who loves Key West, where his family has been living almost 100 years. This amazing experience didn't resemble a dry history lesson. A lot of anecdotes and funny stories from the past were scattered between numerous historical facts. Thank you, Richard, again! P.S.: Good bonus: you will get a list of the best restaurants in Key West.
Great walking tour
NYcountrygirl, 15-12-2022
Richard our guide provided us with a wealth of knowledge regarding the history of Key West and its architecture. Great tour. Learned more about the area in a few short hours.
Fantastic tour and History of Key West
shane_c, 15-12-2022
Richard was a terrific tour guide. He seems to know everything about the Island and it's story. We've been coming to Key West for years but this gave us a different appreciation for its history.
Don't miss this tour!!
ryanhX3591PZ, 13-12-2022
This is THE Key West tour to take. We learned so much about the history and architecture of Key West. Rich was an amazing and personable guide. His knowledge was second to none!
Local history at its best!
loriwU748NF, 12-12-2022
We really enjoyed learning about prominent families who settled Key West and still have influence, seeing beautiful architectural styles (e.g. Bahamian style homes), and so much more! This was such an interesting historic tour! Great stories! Thank you so much!
Wonderful tour
marlenegG9557JB, 30-12-2022
Richard’s wealth of knowledge was amazing! We had a great tour! I would recommend this to everyone who’s visiting key west.
Great tour!
Nomad212740, 27-12-2022
This tour is a must for those who love a bit of history and architecture! We took the tour on Day 1 of our KW stay which was great. Richard was hands-down one of the best tour guides we’ve had. Our 11 year old son was highly engaged on the tour. Richard also can provide a list of restaurants in KW which was helpful too. We are so glad that we came across this tour.
Great tour
I9481DDnicolen, 27-12-2022
Very knowledgeable and interesting tour of historic key west. By far the best tour during my trip. If you don't like a lot of walking you're in luck.
Great historical tour!
Norene_P, 18-12-2022
Learned so much history of the area and about the people who came to develop the area. Plus personal history that our guide shared with us. Would highly recommend it to others.
Couple from Birmingham
heidi_y, 17-12-2022
Our tour guide was fantastic! He was born and raised in Key West and knew so much history of the area. We thoroughly enjoyed his commentary! I would recommend this tour to anyone!
