Annie Cooper Boyd was born in Sag Harbor in 1880, the daughter and granddaughter of boatbuilders who had prospered by supplying whale ships with the small boats that carried harpooners and crew over the waves in the final chase.

Though the whaling industry that had made Sag Harbor a bustling port earlier in the century no longer thrived, the Coopers continued to prosper from their investments and Annie, as the youngest in a large family, enjoyed all the advantages of indulgent parents and an idyllic environment.

We know all this because at age 16, Annie Cooper began a diary that she would keep well into adulthood. Its pages record a young tomboy’s transition to womanhood at a time when a girl who preferred climbing trees to serving tea was perhaps acceptable, but strong will in a woman was not. It recalls a Sag Harbor that was quieter than it was in its heyday but where Annie still found plenty of opportunities for “fun or any mischief”—on horseback, out on the water, or on the loose with her mostly male friends proving that she was “as good as a boy.”

Now Carolyn Oldenbusch and Charles Grubb have taken excerpts from the diary and combined them with the charming watercolors that prove that Annie took pleasure in at least one activity in which proper young women were urged to excel. The result is “Anchor to Windward: the Diaries and Paintings of Annie Cooper Boyd (1880-1935),” whose pages resemble those of an extraordinarily artful scrapbook.

An intimate little book, it speaks with the distinctive voice of Annie,

the diarist, and glows with the vision of Annie, the artist, whose love of nature and deep sense of place kept her coming back to Sag Harbor.

Indeed, “Anchor to Windward,” says Ms. Oldenbusch, “is really a story of how a sense of place formed her character.”

Speaking recently at her Sag Harbor home, where she was joined by Mr. Grubb, Ms. Oldenbusch talked about the book project, which she called “a labor of love,” undertaken to fulfill a commitment made to her friend the late Nancy Willey, the diarist’s daughter.

Ms. Willey, who was well known in the community for carrying her mother’s strong feelings for Sag Harbor into the next generation, was a meticulous local historian and preservationist. She was also committed to preserving her mother’s legacy and spoke often to Ms. Oldenbusch about her desire that Annie Cooper Boyd’s diaries and paintings not be forgotten.

“I had made a promise to Nancy to do something. This was really for her,” said Ms. Oldenbusch.

Ms. Oldenbusch said she had intended to act as both editor and designer of the book. But while working with the text posed no problems for Ms. Oldenbusch, a former curator for the Society for the Preservation of Long Island Antiquities (SPLIA) and the site manager/education director for the Sag Harbor Custom House, design was another matter.

To master the art, she called on her friend Charlie Grubb, whose designs for other books involving Sag Harbor history she admired, to instruct her.

Ms. Oldenbusch said she soon realized the better course was to ask Mr. Grubb to design it himself, a task he accepted with pleasure, having fallen under Annie Cooper Boyd’s spell. Like his collaborator, he said he found himself captivated by her voice, which Ms. Oldenbusch characterized as “optimistic and idealistic” and he called “very honest, very penetrating and sweet.”

Area residents will find “a lot of recognizable places in the book,” said Mr. Grubb, adding that one of the things that impressed him most was the vividness with which Annie conveyed the time and the place, though he stressed that while, for her, the place was Sag Harbor, anyone with a connection to any place could identify with the sentiments she expressed.

When the Sag Harbor Historical Society celebrates its 25th year at its annual meeting on May 15, the book, which was co-published by the Society and SPLIA, will be on sale as part of the festivities, which are also planned as a farewell tribute to Joan B. Tripp, who is leaving her post as president.

The event gets under way at 2 p.m. under a tent on the Custom House lawn in Sag Harbor. Refreshments will be served and there will be a presentation by SPLIA Director Robert MacKay of the paintings by Annie Cooper Boyd to the Society. In addition, the Corcoran Group Historic Preservation Award will be presented to a surprise recipient.