Leading Ladies of Sarasota

Leading Ladies Historical Tour

The past comes to life in an informative and entertaining way on this historical 90-minute city trolley tour led by costumed guide, Kathryn Chesley, as she plays the parts of Mable Ringling (wife of John Ringling), Marie Selby (wife of William Selby and Philanthropist), or Bertha Palmer (Rancher and Developer) on alternating tours.

Find out what Sarasota was like 100 years ago through the eyes of each of these impactful women during the time they lived here. See the historical places in Sarasota and learn about its key development.

Each week’s air-conditioned tour features a different leading lady founder and focuses on her unique contributions to Sarasota.

ALL guests must be 12+.

Every guest must have a paid ticket in order to board.

Tour ticket includes FREE Parking!

PLEASE NOTE: Video, audio and film recording of any performance by patrons is strictly prohibited.

THE REVIEWS ARE IN!

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Perfect ladies day out!! – Apr 2024
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!! — Diane B.

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AWESOME! – Jan 2023
The Penn Alumni Club really enjoyed the Leading Ladies Trolley Tour on Thursday, January 19, 2023. Our guide Kathryn, who came in character as Rose Wilson, was awesome, so knowledgeable and informative! We received so many nice comments from alumni on the tour about how much they enjoyed learning about Sarasota history and landmarks from our wonderful guide. The check-in process at the Trolley Cottage was easy. Alumni enjoyed chatting and waiting for the tour to board on the porch and comfortable seating areas right outside. Please extend our thanks to Kathryn as well. Her expertise, enthusiasm, and interest in Sarasota history made the tour a really enjoyable experience for us! — Sharon

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LOVED IT! – Mar 2022
What an extraordinarily entertaining way to learn about the history of the city of Sarasota! Kathryn was so knowledgeable and witty. The 90 minutes absolutely flew by and the information was remarkable. Personifying Mabel Ringling and speaking in the first person made this tour and all of the info come alive for us. I would do this again in a minute. — Kendra