Leading Ladies of Sarasota

Leading Ladies Historical Tour

Step back in time on an engaging, 90-minute air-conditioned trolley tour that brings Sarasota’s past to life through the voices of its leading ladies.

Kathryn Chesley, historian and tour guide dons the costumes of each woman portraying Mable Ringling, Marie Selby, or Bertha Palmer on alternating tours, sharing stories of their lives and the city’s development 100 years ago.

Each week’s tour focuses on one Leading Lady’s unique contributions while it visits historic Sarasota sites to learn about the early days of Sarasota’s unique history.

ALL guests must be 10+.

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.

What’s Included

• Air-conditioned trolley tour
• Kathryn Chesley portrays all leading ladies in period costume
• Visit to historical places in Sarasota
• Opportunity to visit the Trolley Cottage Gift Shop while waiting to board
• Free on-site parking

Highlights

• Learn about Sarasota’s development through the perspectives of influential leading ladies of Sarasota
• Air-conditioned comfort throughout the tour
• Weekly rotating focus on a different leading lady

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