TOURS RUN RAIN OR SHINE
Discover more about Sarasota with one of our 10 uniquely different trolley & van tours. See all our entertaining tours below!
Travel into the past aboard our enclosed, air-conditioned trolley or high-top passenger van to hear stories of fascinating people, enchanting places, and intriguing events that shaped Sarasota’s amazingly rich culture. Tours run Tuesday-Sunday in high season and are led by the same entertaining Tour Guides whether they are offered in the trolley or the van.
The Psychic, Boutiques & Bubbles, Circus, Amish, Public Art, and Art Gallery Crawl tours generally run in our high-top passenger van. Sunset City, Haunted Sarasota, and Tiki Trivia Trolley tours always run in the trolley. City Sightseeing tours run in either, depending on number of tickets sold.
Tours are designated on the calendar as van or trolley tours as soon as possible, but with last-minute bookings during high season, we may not know until the day before.
Please book in advance so we can plan for your visit!
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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.
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 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.
Enjoy a relaxed Sunday Brunch tour of Sarasota! Explore Sarasota’s charming neighborhoods, then enjoy brunch with live music at Hamlet’s Eatery in the Limelight District.
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!!
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 history of psychics and mediums in Sarasota. Discover Pixie Dust Metaphysical Boutique, Siesta Key Beach, and a labyrinth. You can add a tarot card reading to your tour!
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.
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.
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.
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.
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.
During December join us for a special holiday trolley or van tour complete with cocoa, carols & Christmas stories about Sarasota!