Book Your Group Tour Now!
Discover more about Sarasota with one of our many unique trolley tours. See all our entertaining tours below!
Travel into the past to hear stories of fascinating people, enchanting places, and intriguing events that shaped Sarasota’s amazingly rich culture on one of our many narrated entertaining tours.
November-May, tours run Tuesday-Sunday in the air-conditioned enclosed trolley.
Additional tours are offered in the high-top passenger van. The tour listing will show the vehicle used for the tour.
During low season (June-October) tours do not run every day. Check our full calendar for the tours offered each day.
results result
No Tours found.
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.
Grab your girlfriends for a personal shopping experience, visiting local boutiques on each tour offering clothing, accessories & gifts, home décor, or unique vintage finds.
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!!
During December hop onboard for a holiday adventure filled with songs, jokes, and Christmas trivia!
During December join us for a special holiday trolley tour complete with cocoa, carols & Christmas stories about Sarasota!
Celebrate Saint Patrick’s Day early! This festive tour leads to one of Sarasota’s lively Irish pubs for beer tasting and music, with jokes, songs, stories, and laughs along the way!
A city 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.
Celebrate Valentine’s Day with your sweetheart — enjoy Love Stories of Sarasota aboard our trolley!
Learn about the history of psychics and mediums in Sarasota. Discover Pixie Dust Metaphysical Boutique, Siesta Key Beach, and a labyrinth. You can also add a tarot card reading to your tour!
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.
A whimsical scavenger-hunt adventure looking for rainbows and unicorns through Sarasota’s magical places with tour guide Princess Jenny!
A full day experience with morning City Sightseeing Tour and afternoon at a private beach with lounge chairs and umbrella. Optional add-ons include boxed lunch & soda, hotel transport, and more.
Explore the Soulful Side of Sarasota! Enjoy a fascinating tour around selected charming and historic neighborhoods, then enjoy brunch with live music at Hamlet’s Eatery in the Limelight District.
Enjoy a scenic City Tour at Happy Hour! See the BEST places to visit, shop, and dine in Sarasota’s funky and historic downtown neighborhoods as you watch the sun set on beautiful Sarasota Bay.
Our Tiki Trivia Trolley Tour includes a fun sing-along to favorite Florida tunes, Sarasota trivia contest & a stop at the Bahi Hut, Sarasota’s oldest tiki bar, for a sample of their world-famous Mai Tai.