Sarasota Tour: Kathryn Chesley Portrays Influential Women

Discover the captivating history of Sarasota with actress and tour guide Kathryn Chesley as she brings to life influential women such as Mable Ringling, Rose Wilson, Marie Selby, and Bertha Palmer.

Duration: 1 hour, 30 minutes
Cancellation: 24 hours
Highlights
  • Sarasota - Travel throughout the downtown Sarasota area.
What's Included
  • Bottled water available
  • Air-conditioned transport
Additional Information

Kathryn Chesley, an actress and tour guide, excels in wearing period costumes to portray Sarasota’s most influential women, including Mable Ringling, Marie Selby, and Bertha Palmer. She shares the captivating stories of Sarasota and how these remarkable women and their unique contributions shaped the city into what it is today.
Experience history coming…

Location
1826 4th St
4th Street
Off Fruitville, behind the Breakfast House
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.8
(13 Ratings)
5 stars
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1 star
Laura
Mar 26, 2026
Great Tour! - This is a great tour. This is the third one we have done in The Leading Ladies tours. Great overview of Sarasota, and the people that made this city so great! Highly recommend. Kathryn is fantastic. She does an amazing job portraying the leading ladies of Sarasota. The Discovery Tours does a great job at communication, reminders, information about upcoming tours. We hope to join many more tours since we full time residents. Perfect for residents, visitors, tourists. Tour is the perfect length of time, and the driver is a good guy.
Review provided by Tripadvisor
Karin
Mar 14, 2026
Fascinating tour of Sarasota with Mrs. Tingling! - I truly loved every moment of this tour! “Mrs. Ringling” has such a captivating voice, and I really enjoyed listening to her stories. She shared so many fascinating facts that my mind was racing to keep up! It's obvious the guide has done a lot of research and is very knowledgeable about the history of the Ringlings and other prominent families in Sarasota during that time. I was especially interested to learn about the Scottish immigrants who settled in Sarasota. I think I’ll take this tour again someday because I know I'll only remember a small part of what I learned the first time. I wholeheartedly recommend exploring with “Mrs. John Ringling!”
Review provided by Tripadvisor
Tango223
Mar 12, 2026
A Must Do Tour when visiting Sarasota - I've been living in Sarasota for over 10 years and I wasn't expecting to learn a lot as heard Bertha's story before. I was totally blown away on how much I learned about the history of Sarasota. I saw areas that I didn't know existed ! This is a tour that anyone (including men) should take. I will definitely book it again the next time we have company.
Review provided by Tripadvisor
Global445639
Mar 12, 2026
A tour worth taking - Very enjoyable, very informative tour. I have lived in Sarasota almost 10 years and learned so much more about the city. I call home.
Review provided by Tripadvisor
Laura
Dec 18, 2025
Leading Ladies - Excellent tour. We loved learning more about Marie Selby, Sarasota, and other leading figures that helped to develop Sarasota into the paradise it is now. Kathryn was amazing! This is the second performance we have seen by her. Highly recommend. You won’t be disappointed.
Review provided by Tripadvisor
Karen_s
Nov 21, 2024
Outstanding - Bertha Palmer was outstanding in her deliverance of the story of the leading ladies of Sarasota. The trolley driver did a great job. The scenery was terrific. I have recommended it as a 10+ to a lot of my friends.
Review provided by Viator
W9414lhdianeb
Apr 7, 2024
Perfect ladies day out!! - There were 5 ladies who went on the Rose Wilson Leading Ladies of Sarasota Tour. We are all locals who have lived here for over 20 years. We all agreed that this was such a wonderful tour. The guide portraying Rose was so animated, engaging, and was a wealth of knowledge, not only about Rose & the history of Sarasota, but also took us to areas where we have never been before. It was a thoroughly enjoyable tour & all of us would go again to learn about the other historical ladies, but also to learn more, & see more of our home city. It was a great experience!!
Review provided by Tripadvisor
V6007bujoelf
Apr 4, 2024
It’s a Don’t Miss! Exceptionally good Guide. - Totally engaging & worthwhile. Our Family enjoyed every minute. We can’t wait to schedule another Trolley experience. May do the Amish tour next.
Review provided by Tripadvisor
180judithj
Mar 14, 2024
Early History of Sarasota - Very interesting ride through downtown Sarasota with “Bertha Palmer.” Learned so Much about the early history of Sarasota County You will not be disappointed
Review provided by Tripadvisor
Noel_g
Feb 21, 2026
Sarasota tour - Tour guide was excellent, knowledgeable snd friendly. If anything negative could be saidvit was rather an informational overload and difficult to absorb all at once plus the trolley car was very uncomfortable with wooden seats, no padded backs and very thin seat cushions.. Bring your own cushion! Difficult to be uncomfortable for 90 minutes with no stops making it quite hard for elderly persons such as ourselves.
Review provided by Viator
From $86
up to 4 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).