Book Your Tour 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; Private Group Evening Tours can run other days of the week.
The Trolley Cottage Gift Shop is open:
Mondays-Sundays 9 AM – 5 PM
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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.
Hop aboard our air-conditioned high-top van to see outstanding examples of Sarasota architecture. Tours feature three distinctive styles: Mid-Century Modern, Art Deco, and Mediterranean Revival.
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.
A fun-filled holiday music and light tour for the whole family aboard the trolley, with holiday sing-along and stories, real letters to Santa, jokes and trivia. Book now!
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.
Hop aboard air-conditioned Dolly The Trolley to discover Sarasota’s best food, flavors, and history with local chef and tour guide.
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!!
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.
Enjoy stories of Sarasota’s history, music, jokes, trivia, a gorgeous setting sun driving by Lido Beach and a stop for craft beer at the new Sun King Brewery.
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!
Visit three local art galleries to experience the vibrant Sarasota arts scene. Enjoy wine and appetizers at each gallery while you browse.
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.
NEW Valentine’s Tour! Learn about the love stories of Sarasota’s leading couples, and enjoy their favorite love songs. Free champagne/beer/wine before boarding!
Join us for History Hop, our annual week-long celebration of Sarasota County history in partnership with the Lemon Bay (Englewood), Sarasota & Venice Historical Societies.