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Dst Celebrates Three-Year Anniversary!

a group of people standing in front of a house

Discover Sarasota Tours celebrates its third year in business by offering its Annual Trolley Bash—Retro Style with a fundraiser for the Sarasota Historical Society on Thursday, November 4 at 4:30 PM.

“2020 and 2021 have been a real challenge for us as a tour company,” says CEO Tammy Hauser. “Thank goodness for our ChillMobile ice cream truck, our loyal customers, amazing staff, and this generous beautiful community that helped us make it to our third anniversary.” To celebrate, Discover Sarasota Tours has planned a host of fun activities for the Bash for all of its customers and friends.

Mod Betty with her book, Retro Roadmaps

Appearing at the 2021 Trolley Bash will be Retro Roadmaps author Beth Lennon, a travel writer with a passion for vintage Americana who offers entertaining presentations as her alter-ego, “Mod Betty.”

Food truck Big Blue will be on hand serving a menu of gourmet grilled cheese sandwiches; The ChillMobile will offer ice cream treats including Boozy Pops; The Discover Sarasota Tours Tiki Bar will be serving beer or wine; and the Vintage Sarasota Gift Shop will offer special discounts for guests. Tour guides will be in costume, and you will meet the newest member of our fleet family of vehicles, Dolly the Trolley! Finally, the program will include nationally known author and presenter on all things retro, Mod Betty, who will be highlighting Florida retro buildings in her presentation.

Net proceeds from the event will be donated to the Sarasota Historical Society to help repair the foundation of Crocker Memorial Church. “We are so happy to support this important organization,” says Tammy Hauser. “The Crocker Memorial Church and the Bidwell Wood House are key stops on several of our tours and we want to be able to support their important preservation efforts.”

The Trolley Bash begins at 4:30 and runs until 6:30 in the parking lot of Discover Sarasota Tours at 1826 4th Street in the historic district with FREE ample parking for guests. Tickets are $20 and include all activities but are limited to 200 guests and require a reservation. Book online at

DST Founder and CEO Tammy Hauser says: “I am grateful for all the support we have received from our local customers, tourists and snowbirds, especially during such a difficult time for tourist attractions. This annual party is our way of saying: THANK YOU, SARASOTA!!!”

In the upcoming 2022 season, several new tours will be added:

  • Leading Ladies of Sarasota, a historical tour of Sarasota led by Kathryn Chesley who plays a rotating cast of Sarasota’s founding mothers: Bertha Palmer, Rose Wilson, Mable Ringling and Marie Selby. Wednesdays at 10AM November-May.
  • Murder Mystery Trolley, an interactive theatrical show featuring a fun whodunit mystery to solve. December 2021. Will run Saturday nights at 8 PM.
  • Will Rogers – Special Engagement (led by Steve McAllister), highlights the Sarasota connections of the humorist known as “the Cowboy Philosopher,” with Steve McAllister leading the tour in character as Rogers. January 2022.
  • Art Studio Tour of local artists’ studios. February 2022.
  • Wine & Chocolate Love Tour week of Valentine’s Day with Kathryn Chesley playing the founding women of Sarasota with a stop for wine and chocolate tasting.
  • Dine-Along Trolley is a progressive dinner tour stops at three local restaurants—for appetizer, main course and dessert. March 2022.

These new tours will be added to the ongoing tour themes below:

  1. Amish Experience – led by Kendra Cross
  2. Art Crawl Trolley – led by Jerome Chesley
  3. Boutiques & Bubbles Shopping Tour – led by Tammy Hauser or Kendra Cross
  4. Circus History Tour – led by Bob Collins
  5. City Sightseeing Tour – led by Frank Motz, Pat Canavan, Kathryn Chesley, Jon MacDonald, Steve McAllister
  6. Haunted Sarasota – led by Kaylene McCaw and Daniel Pelissier
  7. Holly Jolly Trolley – led by Jenny Aldrich
  8. Sunset Happy Hour City Tour – led by Jon MacDonald
  9. Psychic Sundays – led by Michael Newton-Brown
  10. Public Art Tour – led by Jerome Chesley
  11. Rainbows & Unicorns – led by Jenny Aldrich
  12. Paddy’s Hooley on the Trolley – led by Steve McAllister
  13. Siesta Beach City Tour – led by City Guides
  14. Tiki Trivia Trolley Tour – led by Steve McAllister

Book online at:

All tours depart from the DST Trolley Cottage, located at 1826 Fourth Street—a cute 1930s cottage near downtown with a charming Vintage Sarasota gift shop and The ChillMobile vintage ice cream truck. Tours take place on “Dolly the Trolley,” Discover Sarasota Tours’ NEW 32-passenger custom trolley, or “Vanna White,” our 9-passenger high-top tour van. Tour tickets and information can be found online at For information call 941-260-9818.

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Discover Sarasota Tours offers many entertaining, interactive, and informative air-conditioned trolley or van tours about the most interesting people, intriguing places, and amazing stories that have shaped Sarasota’s rich cultural past.