Betsey 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 deal-making 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 a several times for beach BBQs and limbo contests. There was only one problem, the friend complained: 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.
It’s a dream many might share: turning a scrap of tropical land into a luxury paradise, a rarefied riff on Robinson Crusoe. And the appeal of such an idea—not to mention the practicalities of it—has only been enhanced in the Covid pandemic’s wake. “When you’re in the middle of Zoom calls, no one knows where you are, as long as you’re not doing it on the beach with palm trees in the background and staff bringing you spicy margaritas,” says Edward de Mallet Morgan, who runs super-prime sales at Estate Prestige Knight Frank and has carved out a particular niche in island-brokering. “Nothing about it feels like normal life,” he adds. “Its incredibly peaceful and good for the soul.” As soon as you’ve tamed the landscape enough to build somewhere to sleep, that is.
Michael Dingman, who once made a lamp at school using a map of the Bahamas for the shade, was mesmerised by the country. “The Bahamas? It was him,” Betsey recalls. “He could get on his boat, and he was free.” Though the family’s base was the ultra-exclusive enclave of Lyford Cay, Michael’s real comfort zone was on the ocean: He would have been happy to spend his life on their 129-footer, the Teel. There was only one problem. “I get seasick,” Betsey says with a laugh. “We’re in the Bahamas, but all I want to do is get to some friggin’ land.”
No wonder Little Pipe Cay was so appealing, though even this couple perhaps underestimated the extent of the work they’d need to undertake. It wasn’t merely that back then—they started in 2001—the Exumas had just emerged from a dark period when they were largely the fiefdom of drug smugglers. “Nobody would go near the Exumas then,” Betsey says. “It was a very dangerous place to be.” It was also the fact that any home in such a far-flung location would need to be entirely self-sufficient.
Betsey recalls how the couple would sit on their moored yachts at sunset, after supper, looking out at the land they’d acquired, brainstorming the best next steps. “There was no master plan,” she admits. Michael engaged in the undertaking with gusto, studying how Disney hurricane-proofed projects. It took three attempts to hire a foreman until they found someone who could handle the sheer scale of the job. They had to dredge the seabed so the seven-foot keel of their boat wouldn’t drag on the sand—and to ease deliveries of construction supplies—and even built temporary basketball courts on the cay so the work teams had somewhere to spend their downtime. While Michael focused on engineering, it fell to Betsey to take the lead on designing the exterior and interior of the home, and she took inspiration from the novel Winds From the Carolinas, which fictionalized the widespread migration of loyalists from South Carolina to the Bahamas after the American Revolution. The home, she resolved, would nod to waterfront houses in her mother’s hometown of Charleston, as well as to the rest of the Bahamian region. She relied on an architect of record to translate her vision to reality, with such flourishes as wide verandas, and on the English interior decorator Nina Campbell. Still, Betsy was pragmatic about every detail—sourcing Campbell fabrics, for example, that were particularly fade-resistant. “You have to buy products that have at least a 20-year life span to them—I’m talking about every screw you put in, every piece of wood,” she explains. “You can’t kid yourself; you have to do your homework.”
Their son David was 12 or so when the yearslong project started, and he has fond memories of the entire experience. They were on an adventure, he says: “The basis of being able to do something in a place like that? It’s being someone crazy enough to fall in love with all these complicated things.” His parents were exactly those people. “They were inseparable and brought an entire construction crew onto the island and formulated something between an ultra-luxury resort and a family compound,” he continues. The backdrop of the Bahamas was particularly vivid. “You’re surrounded by very shallow waters, with shades of blue on top of shades of blue. The views are never the same, and it’s like looking at a picture that constantly changes.”
Indeed, the Bahamas is one of the most popular places to purchase and develop an island for that reason—as well as for the fact that a private plane can reach Miami in an hour or less. Still, there are specific challenges to building there, according to architect Mike Sinesi of New England firm DSK, who has masterminded a dozen or so projects akin to Little Pipe Cay across the region. “The soil is more coral and sand; when you go to compress it in your hand, there’s no clay, so it doesn’t hold together,” he says. “The Bahamas are unique unto themselves for that.” There’s no similar hurdle to overcome in the other hub for private-island development in the region: the Virgin Islands, both British and U.S. The soil there is rockier and reaches right down to the water, which permits more-traditional engineering.
These two clusters dominate the private-island market. Other countries are well equipped with land like this—indeed, broker Private Islands Inc. had more than 200 undeveloped examples for sale and ready for such development at press time. But constructing your own personal hideaway isn’t always straightforward, especially if you stray outside those two prime markets. Take the coast of Belize, for example. It’s dotted with untouched islands, but development is now largely off-limits thanks to a recent decision by the government there to enhance marine-protection programmes. The Grenadines cluster, which includes Mustique, is also less popular than the Bahamas or the Virgin Islands. “It comes with its own set of challenges in barging building materials to it, as it’s a little more distant from the U.S.,” Sinesi explains. “This isn’t just something you write a cheque for and it’s good to go. It takes a lot of planning and innovation to make it work well.”
That’s why many owners opt to hire Ryan West, a superyacht marine engineer who worked for Sir Richard Branson on both Necker and Moskito islands, overseeing renovations to the former and development of the latter from raw land into a world-famous resort. West now runs Island Development Group, specialising in helping other buyers do much the same. He will typically be tapped by a family office as a consultant, first working on a master plan for a potential project for a fee of $300,000 to $500,000, including various consultants. This phase involves everything from building regulations to availability of labour locally, as well as environmental-impact assessments and bathymetric studies of the ocean floor and reefs up to 100 feet offshore. It’s also crucial at this stage to understand the family’s intentions for the island. “Some people are very conservative and just want to relax,” he says. “But we had one family who are very social and went all-out with a DJ setup that comes out on hydraulics from the pool deck and has a huge LED system that wraps around the staircase.” He pauses. “That is someone who loves to entertain.”
Next, West will typically put together a brief for architects, highlighting where the prime views are and wind directions, plus suggested locations for staff housing and where the best beaches (think protected from wind, clear views) can be found. Reverse-osmosis plants, solar-panel sites, and plans for back-of-house functions, such as laundry, also form part of this stage. He’ll then price it out per square foot, working with a surveyor: High-end construction right now in the Caribbean, he notes, costs $500 to $800 per square foot for back of house and $1,500 to $2,500 for primary residences. (West charges either a flat fee for managing the rest of the process or between 1 and 4 percent of the total budget.) “No one has put a spade in the ground yet,” he cautions.
West will also work with local authorities to obtain permits, which usually requires a clear outline of the economic upside for the community—often in the form of jobs—that will result from green-lighting the development. It’s only once approvals are secured that construction begins; that phase usually lasts between three and five years, starting with building roads for diggers and the like to use. Bigger isn’t better, either: Most families snapping up islands for private development should shy away from the largest islands and instead focus on anything 50 acres or smaller—otherwise, it will be logistically and financially burdensome, says de Mallet Morgan. (Consider how selling yachts 100 feet or larger is a tougher, longer process than off-loading a small, nimble, harbour-friendly zip-around.)
Betsy retains the gusto of her house-flipping youth. “As an owner, if you think you can detach yourself from the project, you’ll fail,” she says. “My husband did not listen to what other people thought of him—and people thought we were nuts. We could care less, because when you’re doing something new and different, there’s no playbook—you invent it as you go along.”
Their island dream now has five cottages with a combined total of 11 bedrooms and 14 bathrooms, enough to house 22 guests. But it isn’t quite complete, as Michael fell ill with his first bout of cancer before they could finish the last building, a movie theatre. After a round of treatment, the doctors granted Betsy permission to whisk him away to Little Pipe Cay to convalesce. Michael, a poor swimmer, had typically preferred to stay on their yacht while Betsy swam in the water with their sons. “But I took him in the ocean, and he would float, and we stayed there for three months, to build up his muscles,” she recalls. He recovered, but remained frail for a few years until he was again diagnosed with cancer and passed away. His funeral was held in the chapel on Little Pipe Cay. Now the island remains in the Dingman family’s hands; they briefly put it on the market a couple of years ago for $100 million but had a change of heart. Instead, when they aren’t there, they will occasionally rent it out to a very select few—or as David puts it, “we allow other families to experience what we built there.” Betsy still hopes to finish that movie theater.
Island broker de Mallet Morgan best sums up the impulse driving the Dingmans and other island builders. “If you get a twitch on vacation and need something to do? This is not for you,” he cautions. “Most of my clients buying islands do it to get away from the world a little bit, [to find] solitude and perhaps personal security, but also the value it adds—the value to the family.”
Sales Isles
From the turquoise waters of Honduras to the remote beauty of Brazil, these undeveloped private islands are on the market—an invitation to create your personal Shangri-La. Abigail Montanez
Bahamas
Just two miles from Great Exuma, the 144-acre Clove Cay features two miles of oceanfront with towering trees and three pristine beaches. Existing structures, such as a 3,000-square-foot residence, offer a foundation for redevelopment, while protected azure waters make it ideal for boating. Price upon request, the Isles Group
Honduras
Just off the coast of Roatán, the 67-acre Rose Cay has three sandy beaches and deep waters suited for yachts or a marina. Surrounded by vibrant coral reefs and world-class diving and fishing spots, it’s a secluded retreat with a dash of history—pirate artefacts come included for those with an eye for treasure. $4.9 million, Sotheby’s International Realty
Brazil
Tucked away in the Mangaratiba region of the Brazilian state of Rio de Janeiro, Saracura Island is an almost 48-acre slice of untouched Atlantic rainforest. With approval to build on as much as 30 percent of the island and electricity already hooked up, it’s the perfect canvas for a private getaway. $2.6 million, Sotheby’s International Realty
