Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Sarasota…
    3. /Transportation Tours
    4. /Trolley Tours
    5. /Sarasota Women's History Trolley Tour With Costumed Guide
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Product image 6
    Product image 7
    Product image 8
    Product image 9
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Sarasota Women's History Trolley Tour With Costumed Guide

    Discover Sarasota a century ago through the stories of its leading women

    4.5 stars• 261 reviews

    Duration

    90 mins

    Includes

    Trolley ride, Guide, Parking

    Highlights

    Explore Sarasota by trolley with historian and guide Kathryn Chesley, who brings a leading lady to life in period costume. Her in-character storytelling offers a personal perspective on the city's past.

    • Hear the story of Mable Ringling, philanthropist Marie Selby, or rancher and developer Bertha Palmer, with one featured per tour
    • See historic Sarasota sites and trace the city's development 100 years ago
    • Ride in air-conditioned comfort throughout the tour

    What's Included

    • Free on-site parking

    Important details

    • Ages 10+ only
    • This is a non-stop tour; you'll remain seated for the whole trip
    • Do not bring coolers or alcoholic beverages on the trolley
    • Arrive at least 30 minutes before departure to check in. Trolleys leave at the scheduled time

    Cancellation Policy

    Tours run rain or shine. All sales are final; no refunds for missed tours or no-shows. If you cancel at least 24 hours in advance, the operator will try to reschedule you based on availability or offer a gift certificate. If the operator cancels a tour, refunds are issued within 30 days.

    Product ID: BEYW3D

    FAQs

    Yes. Restrooms are available inside the Trolley Cottage Gift Shop before you board.

    No. Food and drinks are not allowed on the trolley.

    Meeting details

    Trolley Cottage, 1826 4th St, Sarasota, FL 34236

    Experience provided by Discover Sarasota Tours

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Adult

    $67.81

    Ages 10+

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.5
    Excellent
    261 reviews•Google Maps
    204
    20
    7
    4
    21

    Visitors consistently rave about the engaging guides and entertaining theatrical elements that make these tours memorable. Steve, Jon, and Deni get special shoutouts for their knowledge of Sarasota's history, architecture, and local culture, while the costumed actors who appear on themed tours like the Haunted Sarasota experience bring impressive talent and energy. The variety of offerings is notable—from singing trolley rides and psychic tours to circus routes and Amish experiences—giving people plenty of reasons to return for multiple adventures. The interactive nature really stands out. Guests sing along with provided songbooks, enjoy props, and often make stops at local spots like bars or boutiques. Owner Tammy is described as an entrepreneurial spirit focused on customer experience, and the gift shop full of local products adds a nice touch. One reviewer mentioned the owner's heavy involvement during a tour came across as micromanaging the staff, which distracted from the experience. Still, the overwhelming majority describe fun, informative outings perfect for newcomers wanting to learn about Sarasota or locals looking for a unique night out with friends.

    What people are saying

    Review 1 of 4
    5/5

    This experience was the perfect activity to dive into Sarasota, FL. The length was perfect and comfortable, while having many landmarks. I moved here 6 months ago, and was surprised there was so much to learn about my own city and its gems! I strongly encourage going to the Ringling Museum before or after this trolley tour - we had just gone to Ringling Museum the day before, and it made it that much more special to learn how interwoven the Ringling family is to the fabric of this city.

    Photo of Katrina Schreiber

    Katrina Schreiber

    August 1, 2026

    Review 1 of 1
    5/5

    This experience was the perfect activity to dive into Sarasota, FL. The length was perfect and comfortable, while having many landmarks. I moved here 6 months ago, and was surprised there was so much to learn about my own city and its gems! I strongly encourage going to the Ringling Museum before or after this trolley tour - we had just gone to Ringling Museum the day before, and it made it that much more special to learn how interwoven the Ringling family is to the fabric of this city.

    Photo of Katrina Schreiber

    Katrina Schreiber

    August 1, 2026

    Nearby activities

    Siesta Key Tiki Boat Tour with Music & Drinks
    Boat Tours

    Siesta Key Tiki Boat Tour with Music & Drinks

    Cruise Siesta Key’s waterways on a 2024 tiki boat with music, drinks and coastal wildlife views.

    5.0 • 10.3K reviews
    $53/ person
    Guided Kayak Tour to Midnight Pass Beach in Siesta Key
    Kayaking Tours

    Guided Kayak Tour to Midnight Pass Beach in Siesta Key

    Paddle Jim Neville Marine Preserve to water-only Midnight Pass Beach

    4.9 • 3.2K reviews
    $61/ kayak
    Sarasota Dolphin & Wildlife Boat Tour
    Boat Tours

    Sarasota Dolphin & Wildlife Boat Tour

    Experience marine life up close on a comfortable pontoon cruise for all ages.

    4.9 • 443 reviews
    $41/ person
    Jet Ski Rental on Anna Maria Island
    Jet Skiing

    Jet Ski Rental on Anna Maria Island

    Speed, sightseeing, and flexible time on the water

    5.0 • 243 reviews
    $158/ jet ski
    Dolphin Watching Sunset Cruise in Siesta Key
    Dolphin Watching

    Dolphin Watching Sunset Cruise in Siesta Key

    Watch playful dolphins and a vibrant Gulf sunset while enjoying complimentary beer and wine.

    4.9 • 9.2K reviews
    $90/ person
    Shell Key Dolphin Float Cruise
    Boat Tours

    Shell Key Dolphin Float Cruise

    Float, swim, and search for dolphins on a Shell Key beach escape

    5.0 • 3.5K reviews
    $68/ person