The shopping list of the ultra high net worth individual: Private plane, check. Super yacht, check. Personal island ... personal island?

A privately owned piece of island paradise, à la Richard Branson (who has one of the British Virgin Islands) and Leonardo DiCaprio (who has one off the coast of Belize), has become the vacation accessory amongst today’s Hollywood and business titan elite (see 6 Wealthy People Who Owned Private Islands). It’s the bigger-than-Ben-Hur real estate business that’s set a new lifestyle benchmark for the 1% with a taste for the intrepid: In recent years, advancements in communications tech, a growing private jet set and modern airports in far-flung places have made it much easier to own the ultimate island escape. Why bother with St. Barts when secluded white sand beaches, VIP sunsets and pristine aqua waters (perfect for skinny-dipping) can be exclusively yours without a single tourist or paparazzo in sight?

Nearly a thousand isles appear on the market worldwide each year, and depending on your needs, a decent one can set you back anywhere from a measly few mill' to $50 million and (well) beyond. The priciest private island ever (Hawaii’s sixth largest) is believed to have cost entrepreneur Larry Ellison a whopping $500 million or so. Less pricey properties are also available, but luxurious they are not – and many lack housing and other necessities that have to be installed (see Can I Afford To Buy A Private Island?).

Of course, for many deep-pocketed island shoppers, this particular luxury purchase isn’t about cost or return on investment. It’s about passion – the romance-driven search to find a sublime, secret little spot somewhere in the world. As with any other property, however, islands require maintenance and islands don't make that easy. Many conveniences people take for granted on the mainland become logistical – and costly – headaches in a remote setting. Importing provisions (often by barge) and parking the yacht are common examples, but there are numerous considerations to take on board before diving in.

If the world is quite literally your oyster, where will you lay your island hat? It’s a big question that begs many, many more. For instance:

  • Are you seeking a year-round or summer escape purely for your own personal pleasure?
  • Is it intended as a family legacy to be enjoyed for future generations?
  • Would you like to construct a house, compound or a resort on it?
  • Do you prefer to be handy to the mainland, or is remote more your style?
  • What outdoor activities float your leisure boat?
  • Climate: Bracing or balmy? Terrain: sandy, woodsy or something in between? 

You get the drift.

Location, Location, Location

It’s easy to fall in love with the idea of private islands. But beyond the fantasy island daydream, the search for that ideal location encompasses so much: a region’s culture and language; seasonal conditions and what they allow; travel proximity from your usual place of residence; and access to provisions. Narrow down the location list by asking yourself: How far are you willing to travel? How much island time can you realistically enjoy? And have you considered the practicality of getting there? A pristine Polynesian atoll may sound like your tropical heaven on earth, but it comes with a 10-plus hour plane ride if you’re based in the U.S.

Beyond distance considerations, accessing an island generally requires a suitable vessel. If you already have a boat, can the island and its bays accommodate it? Deep-water access for larger vessels is deemed a valuable attribute. And if the island hasn't already been equipped with a dock, you may need to construct one.

It’s also crucial to consider Mother Nature’s moods. Ensure the seasonal forecast complements your vacation schedule and general climatic preferences. There’d be nothing worse than finally arriving at your island escape… just in time for hurricane season, or the fishing lake to freeze over. If you envision certain water sports or recreational activities, do the local conditions (and surrounding waters) support them? Rips wreak havoc on open beaches, while sand flies, poisonous snakes and currents known to carry jellyfish could seriously cramp your holiday style.  

Construction Considerations

It’s fair to assume any island will require some level of construction, even if it's just installing basic infrastructure, utilities or a dock. Are you planning to build a large residence or luxurious hotel? If so, what level of development (if any) is permitted, and can the island’s geography facilitate your dream? Your private island broker should be au fait with local zoning regulations and environmental laws, but obtaining development approval for an undeveloped island can take far longer than buyers might expect.

Sure, your island is surrounded by water. But that's salt water, and you’ll need access to a reliable fresh water supply to survive. Typically, the smaller the island or the rockier it is, the fewer natural sources (rivers, springs) it will provide. Interestingly, obtaining H2O isn’t as big a deal in the tropics, thanks to regular downpours you can save for a sunny day – assuming you have reliable collection measures in place.Otherwise, you may have to allocate a hefty budget for barge transport.

You also need to consider how elevated your island is. Good elevation not only translates to great views, it also withstands changes in sea level. An island at low tide can appear much larger than when the sea is at its highest point. “Absolute beachfront” sounds just dreamy, until the water’s literally lapping at your doorstep. 

Paying For It All

Banks typically don’t finance the purchase of private islands, unless they are income-producing (with a hotel or rental properties for instance), because it’s so difficult to accurately appraise them. In other words, once you've decided on your island paradise, prepare to pay in cash.

Islands are acquired in one of two ways:

  1. Freehold, or buying the island outright, which grants 100% ownership of the land and any buildings on it. This is more common in the Caribbean, Europe and the Americas.
  2. Leasehold, or purchasing the rights for a specific timeframe (generally between 30 and 99 years), functions more like a traditional lease which grants temporary possession through the government entity, corporation, or individual that legally owns the land. Leasehold is more common in Asia and the South Pacific, and is frequently less expensive.

Surprise, Surprise

Regardless of available wealth, anyone shopping for an island needs to understand it’s rarely all smooth sailing, and unexpected surprises can pop up. In fact, you can pretty much put money on it. Rumor has it Nicholas Cage was barred from developing a Bahamas island retreat, thanks to an endangered Bahamian iguana subspecies. David Copperfield, who owns 11 Bahamian islands, has spoken of "everyday problems," such as a broken pipe that required a plane ride just to keep the water running.

The Bottom Line

Private islands have officially emerged as the ultimate lifestyle status symbol. In the market for one? The process isn't that dissimilar to buying a house. It just happens to come with a few more (exotic) considerations. A handful of specialist firms offer private island inventory and brokerage services online: Main players with the majority of global listings are Private Islands Online and Vladi Private Islands. For more thoughts, see How To Buy Your Own Private Island.

Start by asking yourself why you crave an island investment in the first place, then set down your criteria and preferences. Eventually, your dream setting will materialize. And don’t forget to enjoy the ride: Pursuit of the perfect patch is often thrilling adventure in itself. “Islomania” could be the most desirable destination on earth; just be prepared for the hurdles that come with it.