A candlelit table at a swanky restaurant, a romantic evening with a partner or spouse—and the struggle to find a parking spot or flag down an Uber during one of the busiest nights of the year.

This Valentine’s Day, rather than the age-old chocolate and roses date, surprise your loved one with a trolley tour recounting the hidden romance of Sarasota’s history. The tour takes in stories of Sarasota pioneer couples like John and Mable Ringling and William and Marie Selby from the comfort of a nostalgic trolley. Starting at 7:30 p.m., the 90-minute trolley tour includes a stop at Peterbrooke Chocolatier on South Palm Avenue for prosecco and chocolate, and live music from singers Lilian Moore and Richard Caldwell. Tickets can be purchased in advance online here

John and Mable Ringling

Tour guide Kathryn Chesley, a lifelong actress, shares a sneak peek at the night’s love stories. While much of Sarasota’s history focuses on the careers and accomplishments of men, Chesley notes the importance of their wives. “The guys couldn’t have done half of what they did without the women behind them,” she says.

Among the featured Sarasota lovebirds are Mr. and Mrs. Arthur Rowe. Arthur Rowe skippered yachts for the Ringlings and the Selbys. Upon his retirement, he and his wife built a boat-shaped house on North Osprey Avenue, which is currently available to rent as an Airbnb.

The story of John and Mable Ringling features prominently in local memory, with constant physical reminders in the form of street names, a museum and a college. What’s less common knowledge is that the Ringlings got married later in life than was typical: when he was 39 and she was 30. “At the turn of the century if you were 30 years old and not married, there was something wrong with you!” Chesley says.

A less likely couple, a pair of gorillas known as Mr. and Mrs. Gargantua, were known for their dislike of each other. Although Gargantua’s trainers thought he could use a companion, the pair never bonded and had to be housed separately.

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