Clearwater Jolley Trolley CEO, Rosemary Windsor to Retire
After over a dozen years at the locally loved transportation company, she will depart in January 2022
Clearwater, FL (November 10, 2021) – If you have lived or worked in Pinellas County over the last decade, you have undoubtedly met or have been impacted by Clearwater Jolley Trolley CEO, Rosemary Windsor. She has played an active role in the transit system, tourism community and numerous charitable groups during her time leading the organization. Today, Rosemary announced her retirement effective January 14, 2022.
In 2009, the locally famous red and yellow Clearwater Jolley Trolley was on the verge of ceasing operations due to lack of funding, when Rosemary was one of two individuals who proverbially “hopped onboard.”
A business plan was created that included forming a funding relationship with PSTA to run public beach routes. After seeing success, PSTA granted Jolley Trolley “The Coastal Route,” Downtown Clearwater, Dunedin, Palm Harbor and Tarpon Springs on Fridays, Saturdays and Sundays. In 2016, it replaced PSTA’s Route 66 and began servicing the Coastal Route 7 days a week. Rosemary then negotiated a 5-year contract with PSTA to continue operating the North Beach, South Beach and Coastal Route, and subsequently a 10- year contract in June of this year ensuring that the Clearwater Jolley Trolley will continue servicing the area through September 2032.
Since that time, the beloved non-profit has more than quadrupled revenues, increased the employee base by almost 400% and grown the fleet from 6 trolleys to a fleet of 26 by year end. The trolleys have become a community icon that shuttle tourists and residents around Clearwater Beach and from Sand Key to Tarpon Springs daily.
In addition to the regular routes, Rosemary has overseen the growth of the charter business to include providing vintage, unique trolleys to thousands of charters which include weddings, corporate events, pub crawls, family reunions and other private events. Chartered trolleys have even been seen transporting the Tampa Bay Lightning and the Stanley Cup at recent celebrations, Superbowl patrons in 2021 and little pirates at the Gasparilla Children’s Parade.
Rosemary serves on Amplify Clearwater’s Tourism Advisory Committee and is a past member of AchieveHERS . Other community endeavors include being a member of Downtown Clearwater Merchants Association (DCMA) Marketing Committee, SKAL, Bay Area Concierge Association and as a past member of the Board of Directors at Clearwater Marine Aquarium for 11 years. She received the Vocational Award for Integrity in the Workplace from the Dunedin Rotary. Rosemary is a graduate of Leadership Pinellas, Class of 2016.
She is respected by her Jolley Trolley family and will be greatly missed but is looking forward to trading in her Jolley Trolly business plan for a personal one. The CEO role will be filled by Jolley Trolley’s current Chief Operating Officer, Patrick Craven.
About Clearwater Jolley Trolley: Since our humble beginnings in 1982, both residents and visitors have used the Jolley Trolley to avoid parking and traffic problems. From the beautiful oak interiors to the gleaming brass trim, taking the Jolley Trolley is truly a unique ride. Our daily service operates along Clearwater Beach and our coastal route serves Clearwater Beach, Downtown Clearwater, Dunedin, Palm Harbor, and Tarpon Springs. Our “Concierges on Wheels” and our unique vehicles both add to that special ambiance when taking a trolley ride. To further extend our services, we offer charter experiences that range from shuttle services to wedding transportation. We encourage you to explore how to, “Leave your car where you are, ride the Jolley Trolley.”