Sarasota couple are cultural ambassadors, together and separately

We’ve all heard variations on “the couple that (fill in the blank) together, stays together.” For some, it’s “the couple that plays together.” The more devout might favor “the couple that prays together.”

We’re not going to rhyme, but for Sarasota snowbirds Kathryn and Jerome Chesley, who’ve been together for more than 50 years, the expression would be: “The couple that enjoys the arts together, stays together.” 

If you’ve spent any time at Sarasota’s cultural attractions, you’ve probably seen Kathryn and Jerome in action, both separately and together. Both retired schoolteachers from Buffalo, New York, the Chesleys can be found leading trolley excursions at Discover Sarasota Tours, ushering at Asolo Repertory Theatre performances and making the most of Sarasota’s arts scene. 

A former drama teacher, Kathryn portrays local historical figures, including Bertha Palmer, Marie Selby and Mable Ringling, on trolley tours and at library, club and historical society events.

For its 75th anniversary in 2025, the Media Roundtable social club hired Kathryn to portray Rose Phillips Wilson, the editor of a Sarasota newspaper in the early 20th century. Wilson's editorials helped win women the right to vote in 1920. She also was a powerful advocate for the creation of Sarasota County in 1921. (It was carved out of Manatee County.)

In addition to elaborate period costumes, Kathryn’s life as a “reenactor” involves a stunning collection of hats with lots of feathers. Some mirror the millinery of the 20th-century aughts, the heyday of the Gibson Girl, while others are straight out of the Jazz Age.

When Tammy Hauser founded her trolley tour company in 2018, she asked Van Wezel Performing Arts Hall General Manager Kyle Turoff to spread the word “through her Big Apple network,” Hauser says. Turoff’s parents, Bob and Roberta Turoff, ran the Big Apple Dinner Theatre in downtown Sarasota for more than 40 years.

Chesley showed up not long after the casting call went out. She was a perfect fit. “As an historic character performer, she has so much knowledge about the history of Sarasota. She can talk about any aspect, anybody, any street, any place. She's wonderful, a real gem,” Hauser says.

Chesley was Discover Sarasota Tours’ fifth employee. Today, it has 23 full and part-time employees, from the actors who perform on themed tours like the murder mystery “Who Killed the Circus Queen?” to the people who run the gift shop.

Hauser hired Jerome when Discover Sarasota Tours expanded from three tours to nine in 2019. “When I heard from Kathryn that Jerome was an artist, I decided he would be perfect to lead a tour of all the public art in Sarasota,” Hauser says.

Photo by Monica Gagnier

A retired high school art teacher, Jerome is an accomplished watercolorist who is a signature member of the Florida Watercolor Society, where he served as president in 2018. He is also a past president of the Florida Suncoast Watercolor Society. 

During the summer, Jerome teaches at the Chautauqua Institution in Western New York. Founded in 1874 by a Methodist minister and an inventor, the adult summer camp is dedicated to lifelong learning. 

For Jerome and Kathryn, Chautauqua is their summer retreat after a busy season in Sarasota, where Jerome teaches watercolor classes and workshops besides leading tours for Discover Sarasota.

For the sake of privacy, we're not going to tell you where the Chesleys live in Sarasota. After retiring, they moved here during the Great Recession of 2008, when housing prices were tanking across the nation. They first moved to the Broadway Promenade at Tamiami Trail and Tenth Street as one of its original tenants.

But they found the location was too busy because the nearby Publix attracts a steady flow of traffic during store hours. They quickly sold their condo and found a hideaway in a modest pink building closer to the water. Today, their building is dwarfed by The Westin and other high-rises. The Chesleys aren't the first retirees in Sarasota to exclaim (almost in unison), "We couldn't afford to move here today." 

Adds Jerome: "We were teachers, we have pensions, we saved our money, but we're not rich."

The Chesleys do seem to have good luck in real estate, though. They own a couple of properties in Chautauqua, including an apartment building that houses employees of the summer camp and a gallery for Jerome to sell his art. 

In Sarasota, the Chesleys live on the seventh floor of their building, which only has an elevator up to the sixth floor. Having to walk up one flight of stairs was a deal-breaker for some potential buyers, but not for the Chesleys, who welcome the exercise.

Inside the spacious condo is a curated collection of glass art in poppy, aqua and lime green. The artwork stands out in comparison to the neutral shades of the furniture, the flooring and other decor. 

In a built-in cabinet with glass doors in an adjoining room, there is a collection of early 20th-century Deldare pottery that is a nod to their Western New York roots. "It will probably get a new owner one of these days, but it has to be the right one," says Jerome. 

Sharing a love of theater and jitterbug dancing

Asked the secret to their marital longevity, Kathryn says communication is key. To “stay on the same page” each morning they review the day’s schedule over breakfast.

It’s a tradition that dates back to the beginning of their relationship. The couple first met in 1972 at a community theater in Cheektowaga, New York, called The Apple Town Players.

Courtesy image

The newfound little theater took its name from the Indian meaning of Cheektowaga, “Land of the Crab Apples,” but left the “crab” out because it “sounded better,” Jerome says.

He ended up at the troupe because a friend told him they needed someone who could paint sets.

“The theater was just starting,” recalls Kathryn. “Our first show was ‘The Mikado.’” 

At the cast party, Kathryn was swept off her feet by Jerome’s jitterbug moves. This led them to team up on the competitive jitterbug dance circuit and ultimately to marry.

Perhaps because they spent their careers teaching, both Chesleys are still constantly learning, whether it be to prepare a new script for a tour or a class outline for Jerome, or to research a historical figure for Kathryn’s reenactments in Sarasota and Chautauqua.

Though not identical to Chautauqua, the idea of a community where residents are devoted to art and education is also part of Sarasota’s history. 

Unlike Chautauqua, the Sarasota Art Colony, which thrived from the 1940s to the 1970s, wasn’t a formal institution. But its members revitalized an association that today is known as Art Center Sarasota to exhibit and sell their works. This year, Art Center Sarasota celebrated its centennial by reviving its famed Beaux Arts Ball. 

Unfortunately, the Chesleys weren’t able to attend. Had they gone, they would have fit right in. But their dance of choice would have been out of sync with the evening. Even after all these years, they still prefer the jitterbug to the Charleston.