- Most popular daytime tour!
- Year Round
- 10+ ONLY
- 90 minutes
On this classic City Sightseeing Tour, learn where to tour, dine, shop or visit! Get an entertaining overview of Sarasota’s rich history, culture, and neighborhoods.
TROLLEY TOURS RUNNING DAILY RAIN OR SHINE!
Discover Sarasota in style and comfort on one of our many entertaining & informative tours!
Due to limited availability, advance reservations are highly encouraged! Our Trolley vehicle is 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. Our prices are the lowest and consistent here on our website ($48.99 daytime tours and $52.99 nighttime tours, plus tax and handling fees). Please book directly with us, your tour operator, for the best pricing available.
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, dine, shop or visit! Get an entertaining overview of Sarasota’s rich history, culture, and neighborhoods.
Hop aboard our air-conditioned trolley to learn about Sarasota’s distinctive architectural styles. Tours feature Mid-Century Modern, Art Deco, and Mediterranean Revival buildings, homes, and structures.
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.
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!
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.
Hop aboard our air-conditioned trolley to see more than 50 pieces of public art in downtown Sarasota neighborhoods on our Public Art Tour led by painter Jerome Chesley.
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 pie shooter.
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.
A Fun Interactive Musical Adventure for kids of all ages featuring WitchyPOO and her Pumpkin.
Hop onboard Dolly The Trolley to enjoy downtown holiday music and lights tour for the whole family on the Christmas Carol Trolley: Letters To Santa tour. This fun-filled music and light tour features singing cast members: Christmas Carol, Candy Cane, Holly Jolly and Billy Holliday who celebrate the holidays with a Christmas carol sing-along down Main Street, holiday stories, letters to Santa, jokes and trivia, and a charming tour of Sarasota’s downtown neighborhood lights.
Explore Sarasota’s vibrant public art downtown & neighborhood gallery locations. Hop on, hop off at (6) six art gallery and studio locations. Enjoy free beer/wine before boarding, and at galleries while you browse. Art Crawl with us select Fridays, January-March from 5-9 PM.
Join us for History Hop, our annual week-long celebration of Sarasota County history in partnership with the Lemon Bay (Englewood) & Venice Historical Societies, and Sarasota County’s Historic Phillippi Creek Estate.