Book NOW for Halloween Haunted Tours!
Discover Sarasota in style and comfort on one of our many entertaining & informative tours!
Due to limited availability, advance reservations are highly encouraged! Generally tours that begin on the hour run in the trolley and those that begin on the half hour run in the van. Both vehicles are enclosed and air-conditioned. We cannot accommodate wheelchairs.
Check our full calendar for the tours offered each day.
Tours that are running are listed on our calendar. If a tour is not listed, it is not running on that day or time, is already sold out, or is booked for a private event. All available tours and seats are listed on the website.
Private Groups generally run on Mondays.
The Trolley Cottage Gift Shop is open:
Tuesdays-Thursdays 9 AM – 3 PM | Fridays 9 AM – 9 PM
Saturdays 9 AM – 9PM | Sundays 10 AM – 4 PM
We are closed Mondays.
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Learn about Amish & Mennonite cultures in Sarasota from tour guide Kendra Cross. Stops at Alma Sue’s Quilt Shop, The Carlisle Inn & Der Dutchman Amish Kitchen Cooking Restaurant for a sample of delicious pie!
Hop aboard our air-conditioned van to see outstanding examples of Sarasota architecture. Rotating tours feature three distinctive styles: Mid-Century Modern, Art Deco, and Spanish Mediterranean Revival.
Visit three local art galleries to experience the vibrant Sarasota arts scene. Enjoy wine and appetizers at each gallery while you browse.
A Spooky Interactive Musical Adventure for kids of all ages with Miss WitchyPOO and her Magic Pumpkin. Enjoy Halloween treats at the Trolley Cottage!
Join Ebenezer Scrooge and the Spirits of Christmas on this this 90-minute theater experience, a holiday musical aboard our trolley!
Learn about the Circus Secrets of Sarasota by visiting key landmarks and hearing stories of the colorful cast of circus characters, showmen, and performers who called Sarasota home.
On this classic City Sightseeing Tour, learn where to tour, shop, and dine! Get an entertaining overview of Sarasota’s rich history, culture, and neighborhoods.
Learn about Sarasota’s famous murders, haunted buildings, and unsolved crimes on this trolley tour. Keep an eye out for surprise guests along the way!!
An Historical City Trolley Tour led by one of Sarasota’s Founding Women: Rose Wilson, Mable Ringling, Marie Selby, and Bertha Palmer, as portrayed by actress and guide Kathryn Chesley.
On this 90-minute interactive tour, solve the mystery of the Circus Queen’s murder in a fun circus-themed theatrical show aboard the trolley.
Learn about the psychic history of Sarasota. Discover Pixie Dust Metaphysical Boutique, have a sound healing immersive experience, and walk a labyrinth. Add a tarot card reading to your tour!
Hop aboard our air-conditioned trolley or van to see more than 50 pieces of public art in downtown Sarasota neighborhoods on our Public Art Tour led by painter Jerome Chesley.