Best-selling author Adam Mansbach claims that he’s “really bad” at not working. He has spent a lifetime of summers at his family’s longtime home in Chilmark, times full of idyllic pleasures — bodysurfing, grilling fish from Larsen’s, living in a house overlooking a beach — that anyone would find enviable. But Mr. Mansbach cites his time on the Vineyard as his most productive as a writer.

Vacationing on Martha’s Vineyard is a Russo family tradition. “I’m trying to remember the first time we took my daughters to the Vineyard, but I know they’ve been coming every year since they were 10 or 11, maybe even earlier,” said novelist Richard Russo, who in 2002 won the Pulitzer Prize for fiction for his book Empire Falls.

Maggie Shipstead was not yet 30 when she finished her first novel, Seating Arrangements. The story, as she described it in a recent interview, is about “an ever-so-slightly dysfunctional Waspy family holding a shotgun wedding on a resort island.”

Ms. Shipstead has never been to the Vineyard before. It is of Nantucket that she speaks, naturally.

Sean Wilentz is hardly your Quaaludes and vitriol music critic. That may be why the Bob Dylan in America author was commissioned to write the definitive history of one of America’s truly great record companies. Mr. Wilentz is also the Pulitzer Prize-nominated author of The Rise of American Democracy: Jefferson to Lincoln.

When Eric Asimov visits the Island for the book festival it will be his first time on the Vineyard in 30 years. His last trip was marked by trying his first farm-fresh egg. He was in college at the time, sleeping on a friend’s floor, and for breakfast one morning they went to the neighbor’s next door to fetch the eggs for breakfast.

For a parent, a child’s teenage years can be a frustrating time, when adulthood and independence start to rear their twin heads. Most parents, though, have the benefit of knowing the ins and outs of their child, having raised them since birth. But what if you were to skip the younger years entirely and suddenly find yourself a first-time parent to a 15 year old?