Book Your Holiday Tours Now!
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 Group Daytime Tours generally run on Mondays when we are closed to the public; Private Group Evening Tours can run other days of the week.
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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A fun-filled holiday music and light tour for the whole family aboard the trolley, with holiday sing-along and stories, jokes and trivia. Book now!
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.
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 Sarasota’s famous murders, haunted buildings, and unsolved crimes on this fun trolley tour. Keep an eye out for surprise guests along the way!!
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!
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.
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.
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.
Visit three local art galleries to experience the vibrant Sarasota arts scene. Enjoy wine and appetizers at each gallery while you browse.
Hop aboard our air-conditioned van to see outstanding examples of Sarasota architecture. Tours feature three distinctive styles: Mid-Century Modern, Art Deco, and Spanish Mediterranean Revival.
Hop aboard air-conditioned Dolly The Trolley to discover Sarasota’s best food, flavors, and history with local chef and tour guide Kelley.
Join us for History Hop, our annual week-long celebration of Sarasota county history in partnership with the Venice, Englewood and Sarasota Historical Societies.
A Fun Interactive Musical Adventure for kids of all ages with Miss WitchyPOO and her Magic Pumpkin. Enjoy FREE apple cider and cookies at the Trolley Cottage before boarding.
On a tight schedule but want to learn about all the areas that make Sarasota so unique? This tour explores some of the top 10 places in the Sarasota County area.