
Leading Ladies of Sarasota
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.9/5
Based on 14 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Leading Ladies of Sarasota worth booking?
Leading Ladies of Sarasota is a 1.5-hour experience in Sarasota, United States, from $86 per person. It scores 67 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.9/5 rating across 14 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 67 / 100
- Rating
- 4.9/5 (14)
- Duration
- 1.5 hours
- From
- $86 per person
Actress and tour guide Kathryn Chesley specializes in donning period costumes and portraying Sarasota's most influential women -- Mable Ringling, Marie Selby, and Bertha Palmer -- and telling the story of the Sarasota an
What you get
About this experience
Actress and tour guide Kathryn Chesley specializes in donning period costumes and portraying Sarasota's most influential women -- Mable Ringling, Marie Selby, and Bertha Palmer -- and telling the story of the Sarasota and how each of these women and their unique contributions helped to make the city what it is today. 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.
What's included
Included
- Bottled water
- In-vehicle air conditioning
What you'll see and do
Travel throughout the downtown Sarasota area.
Pass by without stopping
Where it starts and ends
Meeting point
Sarasota
Off Fruitville, behind the Breakfast House
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Off Fruitville, behind the Breakfast House
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 4 travelers per booking
- Operated by
- Discover Sarasota Tours
Know before you go
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Guests must be 12+; no children under 12 allowed except on our family tours designed for children 3-11. No children under 3. Every guest must have a paid ticket in order to board.
- PLEASE NOTE: Video, audio and film recording of any performance by patrons is strictly prohibited.
Photos






What travelers are saying
Outty’s summary of the themes that recur across 14 traveler reviews. Written by us, not quoted from reviewers.
The guide
6 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
6 mentionsReviewers describe the commentary as informative rather than scripted.
Good for families
2 mentionsReviewers traveling with kids report it landed well with their group.
Traveler reviews
14 verified traveler reviews for Leading Ladies of Sarasota. Ratings and reviews provided by Viator and Tripadvisor.
Fantastic Tour
Fantastic tour with exceptional, extremely knowledgeable and informative Host! Exposed us to very interesting sites and the historical development of Sarasota. I highly recommend this tour.
Response from the operator: What a lovely review of our Leasing Ladies tour with Kathryn!
via Tripadvisor
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.
Response from the operator: Thank you so much! We look forward to delighting you on future tours!
via Tripadvisor
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!”
Response from the operator: Please come back and experience Marie Selby or Bertha Palmer. Kathryn portrays all three leading ladies of Sarasota with their own history and experiences.
via Tripadvisor
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.
via Tripadvisor
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.
via Tripadvisor
Good to know
- Duration
- 1.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 5
- Verdict
- Solid Choice
Why this scores 67
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Leading Ladies of Sarasota: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Sarasota.
How much does Leading Ladies of Sarasota cost?
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Prices start at $86 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Sarasota usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Leading Ladies of Sarasota take?
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Plan for about 1.5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Sarasota is not rushed.
Is Leading Ladies of Sarasota worth it?
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It holds an Outty Ranking of 67 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.9/5 across 14 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Sarasota, and how flexible the cancellation terms are.
Can I cancel or reschedule Leading Ladies of Sarasota?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Leading Ladies of Sarasota suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 1.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Leading Ladies of Sarasota?
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Around 5 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Sarasota can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Sarasota and add a light layer if any part of the 1.5-hour experience runs outdoors or after sunset.
Where does Leading Ladies of Sarasota start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Sarasota within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Sarasota?
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Sarasota runs dolphin and manatee boat tours out of Sarasota Bay, kayak trips through Lido Key mangroves, Siesta Key beach days and visits to the Ringling estate. On Outty we rank every Sarasota experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Sarasota Guided Mangrove Tunnel Kayak Tour, Sarasota Mangrove Tunnel Guided Kayak Adventure, Manatee Discovery Anna Maria Island. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Sarasota?
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November to April for dry weather and calm bay water. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Sarasota?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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