From her wood-shingled cabin in Maine’s Wohoa Bay, Charlotte Gale can see what she calls “nature 360”—a sweeping, panoramic view of the entire island she often calls home. She isn’t exaggerating: Ducks Ledges Island, which Gale bought earlier this year, is just 1.5 acres in size.
Gale, a 65-year-old massage therapist from New Jersey, may not be your typical private island owner, and Duck Ledges not your typical private island. But with her purchases of Duck Ledges, Gale joined a surprisingly eclectic group that includes the rich and famous, but also a diverse array of developers, adventurers, and outdoor enthusiasts. Asked what unites them, Gale told The Daily Beast: “Everyone seems to have a reverence for nature.”
She added: “And obviously, you cannot fear water.”
There are tens of thousands of private islands in the world, ranging from a few dozen square feet to hundreds of square miles. Usually, they are governed by the laws of a nearby country but restricted to use by the owner alone. Famous island owners include Leonardo DiCaprio (Blackadore Caye, a 104-acre island off the coast of Belize,) Mel Gibson (Mago Island, 5,400 acres in Fiji,) and Richard Branson (Necker Island, 74 acres in the British Virgin Islands.) Uses range from private resorts to hunting clubs to paparazzi-free vacation spots.
Princess Diana is covered in sand by her son Prince William during a private beach holiday on Necker Island in the British Virgin Islands in 1990
Gale, 65, doesn’t need to worry about paparazzi. A former chef and food writer, she bought Duck Ledges after a rent increase—and a decline in business due to the COVID pandemic—drove her out of her previous home in Hoboken.
“I literally just Googled cottages under $400,00 anywhere,” she told The Daily Beast. “I wanted something that expanded my growth … and this just popped up.”
The owner of Duck Ledges, Billy Milliken, purchased it in 2007 but felt he didn’t have the time to care for it properly after buying a bigger island nearby. He listed it for $339,000, generating headlines around the country. But Gale was unaware of all that when she showed up for a trial visit with a single, small backpack in tow.
“It wasn't until we closed that the realtor said, ‘Do you know how many magazines this listing has been in?’” she said. She answered truthfully—no—and said the agent told her: “That’s part of your appeal… We liked the fact that you went in there with your heart reaction.”
The island has a single, one-bedroom cabin with no running water and is nearly inhabitable during the winter so Gale rents a small place on the beach in New Jersey during the cold weather and goes to Duck Ledges for four-to five-day stints in the summer. Her favorite thing to do is walk around the edge of the island and listen to the sounds the waves make as they hit the rocky ledges.
“I look at it like being a steward of a beautiful piece of nature,” she said, adding: “It’s very calming to the heart.”
Chris Krolow also got into private islands through his love of nature. At 19, the entrepreneurial Canadian started a business taking German tourists on camping trips through his native North America. The highlight was always the final night, when the tourists camped out on a private island. The campers, most from big cities, were blown away by the experience, but it only cost Krolow about $20 a head.
“Something sparked at that moment and I thought … I need to buy an island and set up shop there,” he told The Daily Beast.
While Krolow shopped around, he also started uploading photos of the islands he toured to a website he was building for his travel company. This was in the early days of the internet, so an online repository of private islands was a rarity. One day, he says, a man with a private island in Belize reached out and asked him to list it on this website, promising him a commission if it sold. Krolow didn’t believe him, but put up the pictures anyway. A few weeks later, he received a check in the mail for $60,000.
Gladden Private Island owners Chris Krolow and David Keener.
Today, Krolow is the founder and CEO of PrviateIslands.com, an online catalog of hundreds of islands for sale. He also runs a magazine, Private Islands, and hosts a reality show for HGTV called “Private Island Hunters.” He said he has a new TV show in the works in which he helps celebrities purchase islands, though he declined to disclose the network.
Krolow says his clients are generally American entrepreneurs. “Americans don’t want to lease an island, they don’t want a piece of an island, they want the whole island,” he joked. Some are looking for rental properties to generate income, but most are just looking for an ultra-private second home.
“Usually they want to have their friends there, they want to show off to their friends, they have their expensive toys,” he said. “There is often an ego element, especially with the younger buyers.”
Gladden Private Island in Belize.
He gets his fair share of outlandish requests, including more than one from religious cults that wanted to buy in South America. Once, he said, he took a call from the CEO of a large company in San Francisco who told Krolow he and his friends wanted to start their own country.
“He started the call off with, ‘Chris, I don't want you to think I'm crazy,’ and I thought, ‘Well this is going well,” he said. It was not the last time he would receive such a request, nor the last time he’d have to turn it down.
Krolow says he warns clients that owning a private island is more complicated and more expensive than they might expect. Construction requires shipping all materials from the mainland, and most projects require extensive environmental vetting. Simply keeping an island up and running can be pricey, too: Krolow had one client whose diesel fuel bill exceeded a million dollars a year.
Chris Krolow’s private island in Belize.
John Sweeney knows this lesson well. The former CEO of an outdoor advertising company, Sweeney purchased his first island in the Sacramento Delta with a group of friends in 2008. (It was either that or a place in Tahoe or Napa, Sweeney says, but they all wanted to be on the water.) They used the island for kiteboarding and duck hunting, and enjoyed it so much that Sweeney bought two more: Ships Island and Point Buckler, which he set about developing as high-end kiteboarding destinations.
Point Buckler became a go-to destination for San Francisco's millionaires and billionaires.
“They don't want to be near regular people,” Sweeney said. “They wanted to have a small group of like-minded clientele who could interact together and not worry about the outside world.” Running the kiteboarding club on Point Buckler was “probably my most successful business ever,” he said. “Until I got sued.”
The Bay Conservation and Development Commission and San Francisco Bay Regional Water Quality Control Board fined Sweeney $3.6 million in 2015 for depositing landfill in the waters around Point Buckler. Sweeney claimed he was simply rebuilding old levees and actually improving conditions for wildlife, and he appealed all the way up to the U.S. Supreme Court. The court declined to hear the case, and Sweeney is still battling it out with the government in lower courts. He even sold his stake in his other island to pay his legal bills.
“It’s not as simple as it seems,” Sweeney told The Daily Beast. “It’s not like buying a property in the U.S. that's in a subdivision. You really have to have a good legal team to do some research and have someone in that country or that location that specifically knows the issues with the local politics."
Still, Sweeney says he would “totally” purchase an island again—“if I can somehow recover from this.”
“I think islands are cool,” he said. “But it’s a very complex real estate transaction.”
Todd Michael Glaser is an expert in such transactions. A real estate developer who credits himself with helping raise the cost of single-family homes, Glaser regularly sells Miami mansions for tens of millions of dollars. When he saw 10 Tarpon Isle, an island in the middle of Palm Beach, he knew he had to have it.
“It was just a perfect storm,” he said of the 2021 purchase. “It was a once in a lifetime opportunity for us.”
Glaser and his company converted the existing home on the island into a guest house and built a 9,000-square-foot main house with 11 bedrooms, 15 full bathrooms, and seven half-baths. The property boasts a 98-foot swimming pool, a dock big enough for a megayacht, and tennis courts. This spring, Glaser listed the property for $218 million—$45 million more than any home in Florida has ever fetched.
It has yet to sell—Glaser temporarily delisted it earlier this summer—but he has no no doubt it will. The developer strongly believes the growing class of tech millionaires and billionaires will create a historic demand for luxury homes. To prove his point, he listed a rash of mind-boggling sales in recent years: The Weeknd’s $70 million Bel Air Mansion, Jay-Z and Beyoncé’s $200 million Malibu estate, Ken Griffin’s 27 acres of Palm Beach property estimated to be worth $1 billion.
“There’s an upward trend in the single-family, high-end residential [market], and it’s just because of the wealth in the world right now,” he said. “Fifteen years ago, how many people sold their companies for $3 billion?”
Plus, Glaser added, rising security concerns among the ultra-rich make islands even more desirable. Describing his ideal buyer for 10 Tarpon Isle, he said: “He’s sold his company; he’s ready to go; he had a home invasion in California and he wants to get out. He says, ‘Where’s the safest place? Palm Beach. Where's the safest place in Palm Beach? A private island.’”
A view off the coast of Charlette Gales' Duck Ledges Island.
Even for those without billions in the bank, private islands have a way of capturing the imagination. Gale said she received more than 300 letters in the mail after an article about her purchase ran in The New York Times—many of them addressed simply to “Duck Ledges.” (“I don’t know how they got there, but they got there,” she laughed.)
“Everyone just said, ‘I really appreciated the article, it was inspiring that someone followed their heart, and it inspired me to do something I’d been wanting to do for a while,” she said. “For me it’s been really humbling how beautiful the responses have been.”
Though Gale went into the purchase hoping to escape into the beauty of nature, she added: “What I found in that island is that the best of humanity came out.”
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