Back to school – way back: Keewaydin Island once housed a school for winter visitors

Lance Shearer

Keewaydin, the barrier island between Naples and Marco, is an eight-mile strip of white sand, backed by mangrove swamps, dotted with multi-million dollar homes.

Before World War II, though, the island was home to a school – for just a few years.

“It wasn’t ever really very successful,” said Laverne Gaynor, whose family bought the island, known then as Key Island, in 1945. The main attraction on the island, accessible then as now only by water, was the Keewaydin Club at the north end, and eventually the club name became applied to the entire barrier island.

Classes were held in these cottages. In the 1930s and Õ40s, a school was briefly established on Key Island for the children of winter residents. Photo from the collection of the Collier County Museum

“It started out as a camp, for kids who had allergies, and I guess he didn’t realize that all the pine trees weren’t ideal for them,” said Gaynor, now 94. “He” was Chessman Kittredge, a Boston investor, who built a lodge, boathouse, and several small cottages, starting in 1935, as part of a youth program based in Ontario, Canada.

Children of families who were “wintering” in Naples, generally well-off snowbirds from the northeast and Midwest, also attended the school, commuting across Gordon Pass between Naples and Key Island aboard the motor launch Kokomis. While 40 children enrolled in the first season, the project “proved a financial disaster,” says a display at the Naples Depot Museum recounting the early history of Keewaydin.

Naples resident David Teetor, 84, attended school on the island. In the 1930s and '40s, a school was briefly established on Key Island for the children of winter residents.

It was a personal disaster for Kittredge. Convicted of embezzlement, he shot himself on the island in 1936.

“He had borrowed money from the camp, and suddenly it was discovered. Some of the board members were on their way down, and he committed suicide. It was very sad – he had a great deal of vision,” said Gaynor.

Even without its founder, the school continued, and in 1938 Naples resident David Teetor enrolled in kindergarten.

“My mother brought me and my sister, three years older than I, from our home in Hagerstown, Indiana, to Naples for two months in the winter,” said Teetor, now 84. “They would take me out of school in Indiana. When the winter vacation was over, I would go back into school up north.

Lisa Marciano, manager of the Naples Depot Museum, with the display on Keewaydin and the school. In the 1930s and Õ40s, a school was briefly established on Key Island for the children of winter residents.

“In the first grade, I didn’t notice much difference, but when I got back to Indiana for the end of second grade, I was way behind. They were all reading and I was still working on the alphabet!”

School was taught by a married couple, Capt. Sam and Charlotte Shaw. Capt. Sam would also pilot the boat across the pass to the island,” Teetor remembered.

Teetor’s education career on Keewaydin ended in the winter of 1940. He did learn to read, and earned a degree in social psychology from Indiana University, before flying off aircraft carriers for the U.S. Navy. The school continued for several years, having as a pupil another noted Neapolitan, Dr. John Briggs, said Gaynor, but the war proved its demise.

During World War II, “guests were required to keep their room lights blacked out at night, and needed to carry photo identification cards from the Coast Guard in order to travel off the island,” according to the museum display text.

“It was a real chore during the war,” said Gaynor. “They couldn’t get gasoline, or almost any supplies.” The school closed permanently in 1943.

A display at the Naples Depot Museum shows Kokomis, the boat used to ferry children to the school. In the 1930s and Õ40s, a school was briefly established on Key Island for the children of winter residents.

The cottages where school was held are long-gone, along with the teachers, the board of directors and most of the students, but the Kokomis has been preserved, and may be seen at the headquarters facility of the Collier County Museum system next to the government center on the East Tamiami Trail.

The name “Keewaydin” came from Longfellow’s Song of Hiawatha, and is Ojibway Indian word for “northwest wind,” said Teetor.

The school for the wealthy at the northern end of Key Island was a marked contrast to the primitive schools established earlier on barrier islands for the children of the early white settlers, around the turn of the century. Schools on Little Marco island, just to the south of Keewaydin, and Key Marco, were taught by teachers who boarded with their students’ families, and lived isolated lives in those days of no roads, powerboats, or electronic communications.

The Naples Depot Museum, at 1051 5th Ave. South, the Tamiami Trail, just east of 10th Street in Naples, has many artifacts, displays, and recreations of life in Old Naples, including a newly refurbished club car from the Silver Meteor train on the Seaboard Air Line railroad. Admission is free, and the museum is open from 9 a.m. to 4 p.m., Monday through Saturday.