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New “Infamous Sarasota” City Tour

Belly up to the bar!

Discover Sarasota Tours launches a fun new way to explore the city’s colorful history on Friday nights: “Infamous Sarasota” — The Throwback Happy Hour Tour.

Relive the glory days of Sarasota’s sunny and scandalous 60s, 70s, 80s, and 90s with tour guide Jonny Mac! Hear stories of Sarasota’s growth boom, its legendary bars, and the fascinating people who frequented them.

Tickets include complimentary beer or wine at the Trolley Cottage Tiki Bar before boarding.

The tour visits the arts district and other historic neighborhoods, the site of the old Sawmill Inn, and places like St Armands Circle, downtown Sarasota, the Southside neighborhood, the Bahi Hut, and North Trail.

Tour guide Jonny Mac has proudly lived in Sarasota since December 1972. With ties to Van Wezel Performing Arts Center, he worked at the iconic Sawmill Inn Restaurant for more than seven years as bartender/bar manager. He then spent 32 years in the wholesale liquor and wine industry, employed by National Distributing Company, followed by Southern Wine and Spirits. His passion for sports, entertainment, and the history of our beautiful Sarasota continues to grow.

Infamous Sarasota Happy Hour Tours run Friday evenings—starting from March 1 through June 14, from 5:00 to 6:30 PM. Ages 21+ | $35 per person + tax and fees.

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 8 different trolley tours exploring the history, culture, and unique aspects of Sarasota.