Tom Kolar was in the business of selling dreams.
In the early days of Cape Coral, when the canals were freshly cut and the promise of a “Waterfront Wonderland” was still more pitch than proof, Kolar was part of the team that convinced Northerners to move south. Later in his life, he built a Fort Myers Beach motel that let people enjoy a sojourn in paradise.
Thomas James Kolar died in Fort Myers on March 13. He was 96.
Working in promotions for Gulf American Land Corp., Kolar helped greet travelers along the route south, handing out orange juice and brochures and offering overnight stays – a roadside invitation to imagine a different life.
It worked. The city grew to become Southwest Florida’s most populous, with an estimated 233,025 residents as of 2024, according to the U.S. Census.
It worked on Kolar, too. He and his wife, Ellie, were living in Illinois, running a custom cabinet business, when they encountered a Cape Coral exhibit at a home show during a particularly bitter Chicago winter, their daughter, Sandy Stilwell Youngquist, recalls.
“They went back home, sold their business, sold their home, and they bought a 40-foot cabin cruiser,” she said.
The couple didn’t drive south. They boated.
From the Fox River to the Mississippi then down the Gulf, they made their way to a place that was still taking shape. When they arrived at the Cape Coral Yacht Club, they tied up for the night.
The next morning, a man was knocking on the boat with coffee.
It was developer Kenny Schwartz, the company’s first hire.
“He gave him a job,” Stilwell Youngquist said.
Kolar started as a security guard, was later deputized by Lee County Sheriff Snag Thompson, then moved into promotions – a position that suited him better than sales, his daughter said. He eventually became one of the company’s vice presidents, where he helped develop the VIT program: Very Important Traveler, offering free OJ and maps to motorists along U.S. 41, then the main north-south route before I-75 was built, right near The Shell Factory in North Fort Myers.
“He was a very jovial person,” his daughter said. “He didn’t really want to get into sales.”
Instead, he became part of the team that built Cape Coral – not just physically, but culturally – in its earliest years.
Those years were scrappy. When Hurricane Donna struck in 1960, the family and some friends hunkered down together in a motel as the storm tore through.
Kolar helped his family escape the worst of it, tying bedsheets together to get them safely downstairs when the roof blew off and wind made the stairwell unusable. Later, he climbed back up to rescue 4-year-old Sandy’s poodle, Fifi.
“At one point I looked up to all of our friends, all huddled in a room, and I said, ‘Boy, this is a windy day. ‘And everybody’s still joking about that, but that goes to show … my dad had everything under control.”
As Gulf American expanded, sending him traveling to other development sites, Kolar and his wife began saving for something of their own.
In 1970, they built it.
The Eventide Motel on Fort Myers Beach became the family’s next chapter — an all-hands-on-deck enterprise that defined not just Kolar’s life, but his children’s.
They sold their Cape Coral home and moved into the motel itself, living in two rooms connected by a spiral staircase Kolar installed himself after jackhammering through concrete, with his teenage daughter helping wheelbarrow out debris.
“I was his unpaid maintenance man,” she said.
It was a family business in the truest sense. Everyone worked — cleaning rooms, fixing toilets, running operations when the parents were away.
“They didn’t stop,” she remembered.
That work ethic would carry forward: Sandy would go on to become a well-known entrepreneur and restaurateur in Southwest Florida. Her siblings carved their own paths as well — one took over and expanded the family’s hospitality footprint, another became a marriage and family counselor.
“He was very proud of all three children,” Stilwell Youngquist said.
Kolar himself was, at his core, a people person — a lover of conversation, community and connection.
“He was energized by being around other people,” his daughter said.
Later in life, he and his wife traveled extensively – long cruises, RV trips across the United States and Canada.
His perspective held, even in loss.
When Hurricane Ian destroyed their Fort Myers Beach home, Kolar and his wife escaped safely, leaving behind decades of possessions and photos. The couple took it in stride, his daughter recalls. Their attitude: “We have our lives … at some point we knew we were going to have to downsize, and we were going to have to figure out what to do with all of our stuff. Now we don’t have to worry about it.”
It was in keeping with how he lived – focused on what mattered. His guiding philosophy was simple, his daughter said.
“He always would say what goes around comes around.”
And through it all, family remained central.
“He was happiest when he was with family.”
Tom Kolar is survived by his beloved wife of nearly 74 years, Eleanor “Ellie” Kolar; his three children, Beverly Chesnut (Steve), Sandy Stilwell Youngquist (Tim), and Tom Kolar (Melinda); eight grandchildren: Krista Hoffman, Steve Chesnut, Jonathan Chesnut, Corban Chesnut, Chauncey Brown, Erik Brown, Tommy Kolar, and Sterling Kolar; and 15 great-grandchildren: Eden Hoffman, Ellie Hoffman, Steven Chesnut, Karis Chesnut, Ava Chesnut, Emily Chesnut, Paul Chesnut, Luke Chesnut, Tristen Brown, Ethan Brown, Grace Brown, Laila Brown, Quinn Kolar, Blake Kolar, and Tommy Kolar.
He was predeceased by his parents, George and Betty Kolar; his brother, Frank Kolar; his in in-laws, Clarence and Esther Roessler, their best friends and traveling partners over all the years of their lives, his cherished granddaughter, Paris Kolar.
Honoring Tom Kolar
A viewing will be held on Tuesday, March 31 from 12:45–1 p.m., followed immediately by a memorial service at 1 p.m. at McGregor Baptist Church, 3750 Colonial Boulevard, Fort Myers, FL 33966 (main sanctuary).
A funeral procession will follow to Fort Myers Memorial Gardens, 1589 Colonial Blvd., Fort Myers, for those wishing to attend the United States military honors and entombment.
In lieu of flowers, memorials may be made to the Lee Health Foundation, which provided loving care to the entire family for 67 years—including a six-month stay for the premature birth of their granddaughter Paris, who lived joyfully until age 35.
Address: Lee Health Foundation, 9800 S. Health Park Drive, Suite 405, Fort Myers, FL 33908
Amy Bennett Williams is a senior reporter. Reach her at at awilliams@news-press.com.
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This article originally appeared on Fort Myers News-Press: Remembering Cape Coral pioneer and Fort Myers Beach hotelier Tom Kolar
Reporting by Amy Bennett Williams, Fort Myers News-Press & Naples Daily News / Fort Myers News-Press
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