The reality of just getting there
The isolation is the whole selling point, which means just getting there is usually a complete disaster.
Take December 2021. I had a client trying to get his family to this super remote spot in the Caribbean. He assumed he could just take his G650 straight there. Obviously you can't land a Gulfstream on a 2,000-foot dirt patch, so we had to park his jet at a mainland hub and cram everyone into a noisy little Cessna Caravan for the final jump.
Of course, a squall hit right as they took off.
The pilot couldn't land the Cessna safely and had to turn around and dump them right back on the mainland. So now it's 2 AM, I'm sitting in my kitchen in New York, and this guy is absolutely losing his mind over a choppy sat-phone, demanding that I "fix the wind." Fix the wind. I remember eating three stale granola bars around 4 AM waiting for his assistant to text me, just staring at the wall thinking, what exactly does he expect me to do about a Caribbean storm system? He ended up having to sleep in a Marriott. It was glorious.
The part nobody mentions: the plumbing
The brochures never mention the plumbing. They show the beach, the villa and the cocktails. Nobody shows you what happens when the water system breaks.
When you rent these places, you are completely off the grid. You rely on diesel generators and massive reverse osmosis desalination plants just to flush the toilets. In 2019, I had a client drop $400,000 on a week-long buyout in the Bahamas. On day two, the primary water pump for the desalination plant simply exploded.
Suddenly, there was zero fresh water. For forty guests. No showers. No running sinks. No ice.
The island manager basically had a meltdown. We ended up having to wake up some guy with an industrial barge in Nassau, pay him God knows how much to fill it with 5,000 gallons of water, and literally tow it across the ocean in the pitch dark. I had to stand there the next morning and watch a billionaire family try to brush their teeth with warm Evian water because the bathroom taps were completely dead.
Off-menu requests and tipping
A full island buyout is generally around $50,000 to $150,000 a night, which usually covers the room and local food. But the real financial hemorrhage is the off-menu requests.
Ultra-rich people do not like being told "we don't have that." I once had a guy who demanded a highly specific, incredibly rare vintage of Bordeaux for his anniversary dinner on an island in the middle of the South Pacific. The island didn't have it. We eventually found the bottle through a collector in Singapore. Getting it to the island was another problem entirely. Flights, customs, a local broker and finally a speedboat.
The freight costs basically added six grand to the price of the wine. It just got buried somewhere on page four of his final folio, right next to thousands of dollars in jet ski fuel.
Staff drama (what happens when you trap 50 people on a sandbar)
Then there’s the staff. Nobody talks about how insane the crew dynamics get when you trap forty people on a sandbar for months. Put fifty people together on a tiny island and eventually someone is going to lose it. In this case, it was the chef and the chief engineer.
I once had an island manager call me in tears, begging me to delay a very important client's arrival by 24 hours. They had gotten into a physical fistfight over the thermostat settings in the staff quarters. The chef quit on the spot and took the only outbound supply boat back to the mainland. I had to frantically source a replacement executive chef in Miami, pay him triple his normal day rate, and fly him down on a four-hour notice just so someone could cook the client's lobster dinner.
And you still have to tip these people at the end of the week. A standard gratuity for a full buyout is easily $15,000 to $25,000 in cash. Do you have any idea how hard it is to get a bank wire cleared for $25k cash on a Sunday morning in the Bahamas?
Maldives vs Caribbean: which is actually better?
I honestly tried to talk clients out of the Maldives if they were flying from the US. Everyone sees the photos and wants the overwater bungalow, but they don't factor in the 24 hours of pure transit. You do a 14-hour leg to Dubai, try to sleep in a lounge, jump on another flight to Malé, and then half the time the seaplanes are delayed anyway. I’ve had clients arrive so jet-lagged they literally slept through the first three days of their $100,000 vacation.
And God help you if you check a bag. I had one family fly to the Maldives for a two-week buyout. Somewhere during their layover in Dubai, the airline lost all six of their designer trunks. The island boutique was basically useless, mostly just selling overpriced sunscreen and cheap linen shirts. I spent three days fighting with baggage claim over the phone while this guy worth two billion dollars walked around paradise in the exact same stained sweatpants he wore on the flight.
With the Caribbean, you at least avoid that whole nightmare. Yeah, there are bugs. The humidity is awful. But you leave Miami at 9 AM and by lunchtime you're already on the sand drinking rum.
What do billionaires even do all day?
You can only sit in a hammock reading a book for so long before you start to lose your mind. That is why these places engineer absolutely insane activities to keep billionaires entertained.
I'm not talking about a generic snorkeling trip. One client paid a $15,000 premium just to have a PhD marine biologist flown in to dive down and physically point out rare nudibranchs (which are basically just underwater sea slugs) to his twelve-year-old kids.
Yes. Fifteen grand. To look at sea slugs.
Another client wanted to play tennis, but the island didn't have a court. So the island management team spent three days building a makeshift grass court on a flat clearing, complete with regulation nets and freshly painted white lines. They played on it exactly once for twenty minutes, got too hot, and went back to the pool.
People asked me if I ever got to enjoy the beach while working those gigs. Enjoy it? I was lucky if I slept four uninterrupted hours without a generator alarm going off. Never again.
