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Dst Celebrates First Year – New Season Launches October 2019


Discover Sarasota Tours celebrates its first year in business by offering its second Annual Trolley Bash—Oktoberfest Style! This month marks the first anniversary of Discover Sarasota Tours. More than 3,000 people have taken DST trolley tours since its launch a year ago.

Locals and tourists alike have enjoyed learning more about Sarasota’s interesting past, its unique Amish and Circus culture, and its vibrant arts community aboard 14 different tours led by local performers.

DST Founder and CEO Tammy Hauser said: “I am so grateful for all the local support we have received from our guests, tourism partners, TOUR-ISTA members and groups. We have had so many repeat tour goers who get off the trolley and buy a ticket for another tour. I see that we filled a need people felt to learn more about Sarasota. And I am delighted that people who have lived here for years and others who have just visited for the first time have fallen in love with our tours and entertaining guides.”

A private, invitation-only Trolley bash for members, tour goers, media and friends to celebrate this milestone will be held on October 17 from 4:30-6:30 PM with a fun Oktoberfest theme. Siegfried’s, the new German Restaurant behind the Discover Sarasota Tours Trolley Cottage, will provide the catering, and Vince Demor from Orlando will play German accordion music during the event.

In the upcoming 2019-2020 season, several new tours will be added:

  • Boutiques & Bubbles (October – led by Tammy Hauser) is champagne, shopping, and a mini neighborhood tour with treats and discounts offered at each shop!
  • Will Rogers – Special Engagement (November – 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.
  • Holly Jolly Trolley (December – led by Jenny Claus, aka Jenny Aldrich) is a special daytime holiday tour with cocoa, carols & Christmas stories of Sarasota—perfect for families!
  • Art Crawl Trolley (January – led by Jerome Chesley) visits three downtown Sarasota galleries, including wine at each stop.
  • Dine-Along Trolley (February – led by Kristine Nickel) is a progressive dinner tour stops at three local restaurants—for appetizer, main course and dessert.
  • Rainbows & Unicorns (April – led by Jenny Aldrich) is a magical tour of whimsical places in Sarasota. Come in your favorite fairy outfit and enjoy cookies and lemonade before boarding.

These new tours will be added to the 14 ongoing tour themes below:

  • Amish Experience – led by Kendra Cross
  • Circus History Tour – led by Bob Collins
  • City Sightseeing Tour – led by Jenny Aldrich, Christine Cain, Pat Canavan, Kathryn Chesley, Jon MacDonald, Steve McAllister
  • Haunted Sarasota – led by Seva Anthony, with surprise visitors played by Daniel Coppinger and Daniel Pelissier
  • “Infamous Sarasota” Happy Hour City Tour – led by Jonny Mac (Jon MacDonald)
  • Love Stories of Sarasota – led by Kathryn Chesley, with love songs from Richard Caldwell and Lilian Moore
  • Psychic Sundays – led by Michael Newton-Brown
  • Public Art Tour – led by Jerome Chesley
  • Sarasota Sports History Tour – led by Jon MacDonald
  • St. Paddy’s Hooley on the Trolley – led by Steve McAllister
  • Tiki Trivia Trolley Tour – led by Steve McAllister
  • Veterans & Vigilantes – led by Christine Cain

Jenny Aldrich, Seva Anthony, Christine Cain, Pat Canavan, Jerome Chesley, Kathryn Chesley, Bob Collins, Dan Coppinger, Kendra Cross, Jon MacDonald, Steve McAllister, Lilian Moore, Michael Newton-Brown, and Daniel Pelissier.

Book online at:

All tours depart from the DST Trolley Depot located at 1826 Fourth Street—a cute 1930s cottage near downtown with a charming Vintage Sarasota gift shop.

Tour tickets and information can be found online at For information call 941-260-9818. Private groups start at 10+ passengers; for more information, email Discover Sarasota Tours also offers an exciting TOUR-ISTA membership program for serial tour-goers, offering discounts and tickets to the annual Trolley Bash, and programs for nonprofits.


Discover Sarasota Tours offers entertaining, interactive and informative air-conditioned trolley tours about the most interesting people, intriguing places, and amazing stories that have shaped Sarasota’s rich cultural past. We offer 14 different trolley tours exploring the history, culture, and unique aspects of Sarasota, including special holiday tours and other themed adventures, all running year-round.