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New Dine Along Trolley Tour!

a woman sitting at a table eating food

Discover Sarasota Tours


November 7, 2022 — Discover Sarasota Tours launches Dine Along Trolley, in partnership with Sunset Food Tours. This fabulous new foodie tour features progressive dining at three downtown restaurants, starting with small bites, then a main course, and finally a dessert. Along the way enjoy learning about Sarasota’s rich food culture.

Runs Wednesdays starting November 30 from 4:00-6:30 PM.

Includes FREE beer/wine before boarding.


a statue of a personCalling all foodies! Hop aboard Discover Sarasota Tours’ air-conditioned Dolly The Trolley to discover Sarasota’s best food, flavors, and history with local chef and tour guide Kelley Hawks.

Each two and a half-hour fun food-fueled tour begins with free wine/beer in the Trolley Cottage Tiki Bar, and then visits Circo for appetizers, Bavaro’s for Neapolitan pizza, and finally key lime pie at The Reserve.

Levi Kay, owner of Sunset Food Tours, said, “I’m very excited to partner with Discover Sarasota Tours to have everyone on our new Dine Along Trolley Tour try a variety of Sarasota’s local dishes, learn about the history and culture of the area. Plus, it’s a great new way to work up an appetite for dinner!”

“Bringing Sunset Food Walking Tours onboard Dolly The Trolley seemed like a no-brainer,” said Tammy Hauser, founder and CEO of Discover Sarasota Tours. “We get so many requests for dining tours, so I am delighted to be able to partner with Levi and his team to make this tour happen.”

This tour is intended for FOODIES who want a downtown global food-centered experience with a bit of history and fun. Note: Must have at least 10 guests to run tour.

Restaurants include: Circo, Bavaro’s, and The Reserve.

Included: all food, tour, transport, parking and beer/wine in Trolley Cottage Tiki Bar. Drinks at restaurants (other than water), must be purchased separately.

Tour tickets can be booked online at or by calling 941-260-9818. Cottage is open Tuesday-Sunday.

For Groups email



The NEW Dine Along Trolley Tour is presented by Discover Sarasota Tours in partnership with Sunset Food Tours.


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Discover Sarasota Tours is the ONLY local trolley tour company offering the BEST daily entertaining and informative air-conditioned sightseeing tours and nighttime theatrical shows about the most interesting people, intriguing places, and amazing stories that have shaped Sarasota’s rich cultural past. In 2022, Discover Sarasota Tours was recognized by Tripadvisor with the 2022 Travelers’ Choice Award.

All tours depart from the Trolley Cottage Gift Shop, located at 1826 Fourth Street in historic Gillespie Park. The gift shop features charming souvenirs and Sarasota books, gifts, and memorabilia for all ages. The ChillMobile is a 1979 vintage ice cream truck lives at the cottage when not out delivering sweet ice cream treats in the community.