Paradise Found

But buying a raw private island is just the first step in creating your personal Eden. Finishing the project will take equal parts stamina and cash.

- Mark Ellwood

Betsy Dingman has always been a rebel. She left her San Diego home in her mid-teens and was emancipated from her father, a judge, at age 16. “Because I was such a smart ass,” she admits, looking back. She soon found herself a working single mother, earning a living doing several jobs, from owning a laundromat to flipping houses to rehabbing a 31-room hotel. That sense of fearlessness and adventure was immediate on the first, blind date she had with a Wall Street dealmaking guru: Michael Dingman, who was 25 years her senior. Michael, who prided himself on doing things his way, immediately sensed that they were kindred spirits. “That was kind of the bond between us,” she says.

They fell madly in love, which led to a decades-long marriage and more children. They moved to the Bahamas and it was there, while lunching with some friends in the Exumas, that the couple decided, almost on a whim, to take a leap of faith. One of those friends owned a near-deserted island, Little Pipe Cay, further down the chain; it had a few shacks on it, and the group had all sailed there several times for beach barbecues and limbo contests. There was only one problem; the friend complained that his wife hated going there. “So, my husband said, ‘Why don’t we buy it’?” Betsy, now 68 years old, recalls. (Michael died in 2017, at age 86.) She didn’t need him to ask twice. But buying the island was just the beginning of what would be a drawn-out adventure, requiring teamwork, patience, and exceedingly deep pockets.