"Forget everything you know about islands and say ‘I want to buy an island’ and start your research. I guarantee you we’re the first people you’re going to see on the internet or at the bookstore."

This is the first time Chris Krolow, CEO of Private Islands Inc, overestimates my knowledge of islands, specifically the buying and selling of them.

Private Islands Inc resembles the properties it advertises: comparatively small but figuratively immense, beguiling, seductive and yet considerably out of reach for almost all of us. With 800 island properties on their website, over 4 million annual site visitors and 70,000 subscribers, as well as a standalone publication and a TV show, Island Hunters, it operates for a concentrated niche market comprised of the wealthiest elite.

Despite this, business is booming. Founded in 1999, the company sells around 30 properties a year, with prices ranging from a few hundred thousand dollars to half a billion.

"In a sense we’ve created a business where serious island buyers come to us. We don’t need to look for anybody."

Finding fantasy

Fantasy is the bedrock of Private Islands Inc. Krolow first heard the island’s siren song as a boy when, growing up in Canada, he spent time on the country’s many islands, particularly one in the exclusive Georgian Bay region in Ontario. "It always seemed to be what everybody wanted", he says. "Like, imagine having that all to yourself and the mainland being so crowded." More than this, he says he was "always mesmerised by waterfront property", and what "islands look like from the air".

Despite this lifelong love, his company began as a "fluke". While running a separate business in bringing tourists over to Ontario, mainly from Germany, he noticed that of all the typical tourist spots he brought them to, none left so deep an impression as the islands they visited.

"Picture a tiny little island with a campfire and you’ve got these Europeans from big cities who are experiencing all of this and didn’t pay very much for the trip to begin with", he explains. "I mean, who doesn’t want to be surrounded by water and who doesn’t want, when they’re spending time with family and friends, to have that extra bit of separation from the mainland so you can connect a little bit better?"

A career shift gradually followed, as Krolow set about rooting out and distilling what he calls the "simple pleasures of island life" for the fabulously wealthy. Despite having no experience in real estate, Krolow worked in tourism and ran a website company that advertised his tours. In the process of searching for an island to purchase himself, he got to know island owners in Canada, and decided to display their properties on the site.

"There was actually no plan behind it at all, we just wanted to show off the islands."

A hidden market

Unknowingly, he had stumbled into a hidden market: "I get a call from this guy in Panama who has an island for sale in Belize. He was so happy to meet me and was like, ‘I’ve been trying to sell my island, I had no way to do it. There’s no agents out there’. I says he could put it on our site and told him that I wanted a fee, like $200 or something like that. And he says ‘I’m not paying you two hundred bucks, blah blah blah, I’ll get you a commission’. Six weeks later exactly from that phone call, we got a check for $60,000."

Krolow and his team set about expanding their network, capitalising on what he called the "secret market" of island real estate wherein information about properties coming up on the market is passed through word of mouth from friend to friend, neighbour to neighbour such that the public doesn’t even hear about it. As an example, he explains that of the six properties in the exclusive Georgian Bay area that went sold this year, the public would have only known about three.

Private Islands lists over 800 properties, from Asia to the South Pacific and beyond. (Photo: Planet Observer/Universal Images Group via Getty Images)

Twenty years of business later, and they are the de facto agency for island owners.

"We’ve created such a concentrated niche for this industry that if an island isn’t on our website and it’s for sale, then technically it’s not really for sale. People wouldn't know about it or they might be suspicious as to why it’s not on our site," he explains.

"People had told me I should try and branch out and since the islands are working maybe sell waterfalls or lakes, or castles. And I just stuck with the islands."

Krolow concedes that he’s not your average real estate agent. The process more closely resembles matchmaking, a series of pushes and pulls between owner and buyer. "A lot of the time the owner doesn’t necessarily want to sell the island but they need the money - what do you do? A lot of the time somebody wants to buy the island but they’re too afraid to because they don’t know what they’re getting themselves into."

So, let’s break that down.

Buying an island 101

In their free Buyer’s Guide, Private Islands Inc caution that your island, "this little piece of land that will become more yours than anything you’ve owned in your life", has the very real potential to derail your life with its siren call over the waves. Private Islands are the leading agency in the island business for a reason, and their practices are designed to teach the island-uninitiated everything they need to know about the arduous process.

Central to this is the difference between freehold and leasehold properties, as this will dictate how much freedom you have to craft your personal paradise. Freehold leases are the most similar to what we recognise in property ownership, giving the buyer total control of the island within the confines of the law. There are still some restrictions, such as certain maritime laws that prevent specific waterfront properties from being owned privately.

Leasehold properties, however, are more restricted, and most common in countries across Asia and the South Pacific. A non-national buyer doesn’t purchase the property, but rather the permission to use the land for personal or commercial use, while a government, corporation or another person legally owns the island. "They are sensitive, and if they’re leasehold that means foreigners can pay money to use them and add to their infrastructure and bring jobs and bring money, but they can’t own them", Krolow explains. Leases range in length from 30 years to 99, so if bequeathing your paradise to future generations isn’t a priority, I’d pluck for leasehold.

This is to say nothing of the governmental restrictions, the need for development permits, environmental studies that can take years and proper zoning, as well as a good lawyer to oversee all of this. Once letters are stamped and your own private paradise is secured, building infrastructure is next, with buyers often having to hire labourers through language barriers and a general lack of local knowledge. It seems simple pleasures are hard won.

Fantasy may have gotten you on that helicopter circling islands off the coast of Mauritius, but fantasy doesn’t build villas or install WiFi. In the sage words of Private Island Inc, "While you may have fallen in love with your new island, it’s important to stay sharp and not let your fantasies cloud your vision."


When John Donne wrote, in 1624, that "No man is an island entire of itself; every man/is a piece of the continent, a part of the main", he could have no conception of the "visionaries" yet to come, who in response to the mythical call of sirens on the rock, bought the rock, built 12 villas on it and kicked out the sirens. In these settings, man is the continent, and possessed of the means needed to keep out as much of the unwanted, real world as he or she likes.

Who are these first-class recluses, these idealistic purists chasing a home on the meeting place between solitude and connection?

Krolow concedes that he’s, maybe, a little too close to be objective.

"I live in a bubble, because of the show too, I spend three or four days with these buyers and they all own islands", he says. "It’s so funny, all my friends own islands, literally, and you should hear our conversations, especially up at Georgian Bay. ‘Oh, we’ll have drinks on my island!’ We sound like a bunch of rich, crazy people."

"But in all honesty, I love island owners", he adds, fervently. Struggling to capture their essence, he says "crazy would not be the right word. A little eccentric, stubborn, straight to the point, entrepreneurial. They think outside the box, they like projects. It’s usually magazine cover-worthy."  

"I love that in people. One of the most attractive traits I find in a person is ambition, that sparkle. I see it in my kid’s eye."

Grand designs

It sounds logical to say that fantasy allows for, and even encourages, vaulting ambition. When the laws of the real world are suspended and possibilities are as endless as the cerulean reefs at your feet, the facts of life as a member of the human race drift easily away. Thinking outside the box is all well and good, but when you’re a few hundred kilometres off the coast of Indonesia, it’s less a question of thinking outside of it and more about forgetting the box even exists.  

Krolow is forthcoming on how demanding his clients are. "Imagine this scenario: you’re shopping for property and you’re looking out at these beautiful views and he’s like ‘Chris, this isn’t it because I can see the red roof of the boathouse about a mile away’. How’s that for crazy?"

Krolow understands their relentless verve, and what is at stake when searching for the perfect island: you’re trading in fantasy, a fragile and, frankly, precious thing.

Islands are beacons for ambition and fantasy

"You’re painting this picture of this perfect spot and now you see this red roof and you know someone might be in there working or cooking or whatever, and it just ruins the fantasy of ‘I’m the only person on the planet, I’m here with my family alone.’"

Aside from governmental restrictions and the risk of falling too hard in love with your island, privacy is the main concern for prospective island buyers. Here, Krolow speaks about the islands in Mauritius and how they’re all too close to the mainland, reducing their level of privacy. His tone is frustrated and protective, and it is the first time privacy is referred to in the same awed tones as a new currency.

Hidden costs

This is the new frontier of upscale living, spending obscene amounts of money to hide your extravagance from prying eyes.

Krolow himself has entered a dizzying new level of entrepreneurship. Progressing from rooting out the properties that slot into his clients’ fantasies, he is now developing resorts that cater specifically to their every desire. Gladden, Krolow’s premier resort on the Belize Barrier Reef, is only accessible via helicopter and includes all of the amenities befitting a luxury resort. With room for just one couple, the guests frolic in near total seclusion.

"I’m looking through all of my clients’ eyes and the kinds of people that have the money to stay at this place and what they’re looking for", Krolow says. "It’s so private that when you’re on this island you cannot see any other structures on any other islands, anywhere. In fact, you’re facing the second largest reef in the world, so you’re looking out onto open water but not boring open water: corals and different colours."

"We even designed the whole place so that you can’t see the staff. They’re actually on a smaller island tucked behind it, and the way the landscaping has been done, you can’t see them." When the staff come to clean, lights in the room switch on, so that the guest know they’re there.  

Why the intense need for privacy? Krolow says that people traveling nowadays want "an experience", that their hectic lives make it difficult for them to fully switch off without total solitude. "When people only have a  few weeks off in the year they want to get it right and they’re looking for adventure and an island, it kills a lot of birds with one stones because it’s achieves so much." Still, this seems like a deep dive into alone time.

It is difficult to not wonder what real life expectations this fantasy is this creating. That families appear to have endless luxury at their doorstep without faces to attribute the work to.

Moral compass

It’s just one ethical question that this industry poses, another - more pressing - one being the movement of wealthy business people into developing countries and how to do so with respect. The leasehold properties work to protect some sensitive communities from possible exploitation, but there have been "problems", Krolow says.

He trusts that "anyone who’s going to be doing something higher end, who’s going to be investing money, they’re working with the government and they know what they’re doing", and points out that many resorts will prioritise community involvement. "Whether that’s just to look better or whether it’s coming from the heart, I don’t know."

Just as a private island is beacon for wholesome, albeit grandiose, aspirations, so too does it attract more nefarious ambitions.

Each week, Private Islands Inc. receives applications from people wanting to start their own countries. "And they come with lawyers: ‘I represent blah blah blah, and they would like an island that has this, this and this and has sovereignty where we can issue our own coins and our own stamps and our own passports.’"

He assures me this isn’t possible.

As well as this, cults, high school kids and entrepreneurial types looking to invest big time into sex tourism are frequent applicants. Krolow typically sends them off with a plug for the magazine.

For whom the island calls

It’s undeniable that Private Islands is succeeding in an extremely niche and nebulous industry. But how sustainable is it? The stereotype of A-list celebrity types choosing islands as their second or third holiday homes has been superseded by a more enterprising cohort of island owners, ones that develop their islands and incorporate commercial business there too. It’s conceivable that factors like climate change will curb the selling points of certain properties, and in some cases even raise questions about stricter limitations on vulnerable locations.

"A lot of island owners have pictures of their islands in their wallets", Krolow says

With page views clocking in at over 50 times the amount of subscribers, perhaps what Private Islands really sells is a lifestyle, something to aspire to. But there’s clear joy and a special kind of appreciation in the island owner community, and why not? It’s a monumental undertaking, a responsibility larger than many of us will ever experience and a privileged perspective on the beauty of the world.

"I’m not kidding, a lot of island owners have pictures of their islands in their wallets", Krolow says. "I do. My kid’s is first, but right behind him is my island in Belize."

He knows this sounds a little crazy but, this is the stuff of childhood dreams. It was his childhood dream. He’s still mesmerised. "Just look at some of the aerial photos on my website, that green and blue, the white sandy beaches... Just looking at them, I don’t know, it evokes some kind of emotion in me."

Still, fantasy is always just that. He tells me about night time on Gladden, and how there’s a little red light that flashes from some far off tower that he can do nothing about. "But it bothers me". He says the pulsating red light disrupts the nightscape, it fractures the fantasy. "If you spent years trying to build this place and you had this vision, trust me, it would bother you, too."