Leading Ladies of Sarasota: Historic Trolley Tour
Difficulty
easy
Duration
1.5 hours
Fitness Level
No special physical fitness required; the tour involves mostly seated riding with minimal walking.
Overview
Explore Sarasota’s history from the perspective of its most influential women on a 90-minute costumed trolley tour. See the city’s top historical sites and hear captivating stories that bring the past to life.
Leading Ladies of Sarasota
90 minutes in peak season • Ages 12+
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Adventure Photos
About This Adventure
Experience Sarasota's rich history on a captivating 90-minute trolley tour led by costumed guide Kathryn Chesley. Discover the city's past through the eyes of influential women like Mable Ringling and Bertha Palmer, as you explore key historical sites and learn about their lasting impact on the community.
Leading Ladies Historical Tour
Duration
90 minutes in peak season
About
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.
Departure/Return Location
1826 4th Street in Sarasota (behind The Breakfast House off Fruitville)
Arriving
Please arrive at least 30 minutes before the tour leaves, to check in and visit our gift shop while you wait to board. Trolleys leave at your scheduled time. If you don't arrive within 5 minutes of departure time, we reserve the right to resell your ticket.
Parking
FREE on-site parking is available!
Things to Note
- This is a non-stop tour and you should expect to be seated for the whole trip.
- No coolers or personal alcohol are allowed on our tours. No alcoholic beverages are allowed on the trolley.
- Visit the Trolley Cottage Gift Shop, offering unique Sarasota merchandise while waiting to board.
- We also offer group tours of 20 or more for any regular tour—or let us create a custom tour for your group!
Adventure Tips
Arrive Early for Best Seating
Getting to the trolley stop 10 minutes early ensures you can pick a window seat for perfect views and photos.
Bring Water on Warm Days
Florida can get quite warm even on a short tour, so carry a bottle of water to stay hydrated.
Wear Comfortable Shoes
Though the tour is seated, some brief walking may occur getting on and off the trolley.
Prepare for Variable Weather
Florida weather can change quickly, so bring a light rain jacket or sun protection.
Local Insights
Wildlife
- Great Blue Heron
- Florida Scrub Jay
History
Sarasota’s growth was heavily influenced by pioneering women who contributed to arts and community development in the early 20th century.
Conservation
Local efforts focus on preserving Sarasota’s coastal environment, ensuring tours respect community sustainability practices.
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Frequently Asked Questions
Recommended Gear
Water Bottle
Stay hydrated during the warm weather and longer daylight hours.
summer specific
Sunscreen
Protect your skin from Florida's strong sun exposure during the tour.
spring specific
Light Rain Jacket
Be ready for sudden rain showers common in the fall months.
fall specific
Comfortable Shoes
Wear shoes that are comfortable for any brief walking during boarding or exploring stops.