Skip to primary navigation Skip to content Skip to footer
Back to Newsroom

New Sarasota Sports History Tour

old photo of golfers in the 1940s

Discover Sarasota Tours launches a great new way to explore Sarasota Sports History, including major league baseball, golf, tennis, watersports and much more.

Tour guide Jon MacDonald shares his love of sports and Sarasota sports history by showing some of the key places, important people and legendary events that shaped Sarasota’s sporting history. Tour-goers learn about John Hamilton Gillespie, who brought the game of golf to Sarasota in 1905. They’ll visit Payne Park, the original home of baseball spring training for the NY Giants, Boston Red Sox, LA Dodgers, and Chicago White Sox; City Island Park, home of the Sarasota Ski-A-Rees Water Ski Show; Bobby Jones Golf Club; and end up at Ed Smith Stadium, current spring training home of the Baltimore Orioles.

Tour guide Jon MacDonald 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.

Sarasota Sports History Tours run Sundays during Spring Training season. The first tour is at 1:00 PM on Sunday afternoon, March 3, followed by regular tours Sundays mornings at 10:30 AM from March 10-31. The Sarasota Sports History Tour switches to Saturday mornings at 10 AM starting on April 13. Ages 12+ | $30 per person + tax|fees. 

On Spring Training home game days, tour-goers can opt for a Spring Training Tour + Transport package for an extra $10, which includes pickup and dropoff at Ed Smith Stadium. See details at the Discover Sarasota Tours website.

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. 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.

# # #