I thought I'd made it until I saw how rich people really vacation at these 9 places

I was sitting in first class, sipping champagne on my way to a boutique hotel in Tulum, feeling pretty damn successful. After years of grinding in restaurant kitchens and working my way up through luxury hospitality, I'd finally reached a point where I could afford the finer things. Or so I thought.

Then I spent the next decade serving ultra-wealthy families at high-end resorts and organizing charity galas for billionaires. What I witnessed completely shattered my understanding of luxury travel. The vacation experiences I thought were the pinnacle? They were basically the kiddie pool compared to how the truly wealthy vacation.

Here's the thing: there's rich, and then there's RICH. The difference isn't just about money. It's about access, privacy, and experiences so exclusive that most people don't even know they exist.

After managing events for elite clientele and serving families whose net worth had more zeros than I could count, I learned that real luxury operates on a completely different plane.

Let me take you behind the velvet rope and show you nine places where I discovered how the ultra-wealthy really vacation. Trust me, it's nothing like what you see on Instagram.

1) Private islands that aren't on any booking site

You know those private island resorts you can find on luxury travel sites? The ones that cost $5,000 a night? Yeah, those are for regular rich people. The ultra-wealthy don't share their islands with other guests, no matter how exclusive the resort claims to be.

I once helped coordinate a week-long retreat for a tech founder who rented an entire island in the Caribbean. Not a resort on an island. The whole island. It came with a staff of 30, including a Michelin-starred chef I'd worked with years earlier, three massage therapists, and a team whose only job was to rake the beach each morning before the family woke up.

The kicker? This island doesn't have a website. You can't Google it. The only way to book it is through a specific concierge service that requires a referral from an existing client. The owner told me he turns down 90% of inquiries because he only wants guests who understand that true luxury means never having to see another tourist.

The cost for a week? More than most people's houses. But for these families, the price of absolute privacy and control over every detail of their environment is a bargain.

2) Yacht hopping in places you can't pronounce

Forget Mediterranean yacht charters that dock in Monaco or Santorini. Those are practically cruise ships compared to how the ultra-wealthy do yachting.

During my time organizing high-profile events, I worked with a family who spent summers yacht hopping through the Svalbard archipelago near the Arctic Circle. They'd helicopter between friend's yachts, each one positioned in a different fjord, having dinner on a different $100 million vessel each night.

The crews would coordinate months in advance, shipping in specific wines, flying in chefs from favorite restaurants, and even arranging for string quartets to be helicoptered in for sunset performances on deck. One evening, they had a famous DJ flown in from Ibiza just to play a two-hour set for eight people.

What struck me most was the casual coordination between these yacht owners. They'd created their own floating society, moving together through remote waters where they'd never encounter regular tourists or paparazzi. It was like watching a secret club operate in international waters.

3) Buying out entire luxury safari camps

When I first heard about luxury safaris, I imagined stunning lodges with infinity pools overlooking the savanna. And sure, wealthy people do that. But the ultra-rich? They buy out entire camps and bring their own staff.

A client once invited me to help manage a family reunion at a safari camp in Botswana. They didn't just book the presidential suite. They rented all 12 tents, flew in their personal chef from New York, their kids' tutors, a yoga instructor, and even their family doctor.

The camp's staff was supplemented with the family's own team. They modified the entire camp's schedule around the family's preferences. Game drives started whenever they woke up. Meals happened when they were hungry, not at set times.

They even had the camp's helicopter on standby for spontaneous trips to see specific animals their kids wanted to photograph.

The most surreal part? They did this every year at different camps, treating Africa's most exclusive lodges like their personal vacation homes.

4) Antarctic expeditions with custom everything

While some affluent travelers join luxury Antarctic cruises, the ultra-wealthy charter private expeditions with hand-picked scientists, photographers, and guides.

I learned about this world when coordinating supplies for a billionaire's Antarctic expedition. They chartered a research vessel, but retrofitted it with luxury cabins, a wine cellar, and a kitchen that could handle their dietary requirements. They brought two Michelin-starred chefs because, and I quote, "one might get seasick."

The expedition included a team of marine biologists, a NatGeo photographer as their personal documentarian, and even an artist to paint landscapes. They arranged for a temporary camp to be set up inland for a champagne dinner under the Antarctic sun. The logistics involved were mind-boggling, requiring permits that took a year to secure.

The price tag for three weeks? North of $2 million. But as the client explained to me, you can't put a price on giving your children dinner with penguins in Antarctica with no other tourists for thousands of miles.

5) Japanese ryokans you've never heard of

Everyone knows about luxury ryokans in Kyoto. But the ultra-wealthy stay at places that have been serving the same families for centuries, places that don't accept new guests without a formal introduction from an existing patron.

Through my work with a hospitality consultant, I learned about ryokans that have never appeared in any guidebook. These aren't just exclusive. They're invisible to anyone outside a specific circle. Some have been in operation for 500 years, serving the same families generation after generation.

One client described staying at a ryokan where the chef prepared a meal using recipes that had been served to her family for 200 years, using ingredients from the same suppliers her great-grandfather's meals came from. The owner had records of her family's preferences dating back generations.

These places don't advertise. They don't have websites. They survive entirely on relationships maintained over centuries. The idea of a stranger calling for a reservation would be as absurd as trying to join a family reunion.

6) Wellness retreats that cost more than medical school

Forget the $10,000 week-long wellness retreats in Bali. The ultra-wealthy go to medical compounds in Switzerland where teams of doctors create personalized health optimization programs that cost more than a year at Harvard.

I once helped arrange logistics for an executive who spent three weeks at a Swiss medical retreat. It wasn't a spa with nice doctors. It was essentially a private hospital dedicated to one patient. They ran every conceivable test, created a personalized nutrition plan based on his genetics, and had a team of 15 specialists focused solely on optimizing his health.

The facility looked more like a boutique hotel than a clinic, complete with a private chef who worked with the nutritionist, a sommelier who selected wines based on his treatment plan, and views of the Alps that probably had healing powers of their own.

The treatment included everything from stem cell therapy to experimental treatments not yet available in the U.S. By the end, they'd created a health protocol so detailed it came with its own app and a team available 24/7 for the next year.

7) Scottish castles that aren't for rent (until they are)

There are Scottish castles you can rent online. Then there are Scottish castles that belong to families who might let you stay if the introduction comes from the right person and the offer is substantial enough.

During a stint working with European clients, I learned about castles that technically aren't available for rent but somehow become available when the right person inquires. These aren't commercial properties. They're family homes that open their doors to certain guests who understand the unspoken rules of old money hospitality.

One family I worked with stayed at a castle where the owner, an elderly earl, joined them for dinner each night, sharing stories about the ghost in the tower and the time Churchill stayed in the same room. The staff had been with the family for generations. The head butler's father had served the earl's father.

The experience included hunting with the earl's gamekeeper on land that had been private for 400 years, using rifles that had been in the family since the 1800s. There was no price list for this. It was arranged through relationships and understandings that money alone could never buy.

8) Space hotels (yes, really)

While most of us are impressed by overwater bungalows, the ultra-wealthy are already booking spots on space hotels scheduled to open in the next few years.

Through my connections in luxury hospitality, I've learned about people putting down deposits of $5 million or more for a week in orbit. These aren't just rides to space. They're fully functional hotels being built in orbit, complete with gourmet dining, viewing lounges, and suites with better views than any penthouse on Earth.

One client showed me the plans for his upcoming stay. The preparation alone takes six months, including physical training, custom space suit fittings, and planning meals that work in zero gravity with a chef who trained with NASA. They're even working on ways to serve wine in space, because apparently, that's a priority.

What amazed me was how casual he was about it. For him, space was just the next destination after he'd been everywhere on Earth.

9) Bhutan, but not the way you think

Bhutan already limits tourists and charges a daily fee. But the ultra-wealthy experience Bhutan in a way that makes the regular luxury tours look like backpacking trips.

I learned about this through a former client who spent three weeks in Bhutan with unprecedented access. They didn't just visit temples. They had private audiences with monks who never see tourists. They stayed in the royal family's guesthouses. They attended ceremonies that outsiders typically never witness.

Their guide wasn't just a tour guide but a scholar who had written books on Bhutanese culture. They had a helicopter for transportation, avoiding the winding mountain roads that regular tourists navigate.

They even participated in a private festival arranged specifically for them, complete with masked dancers and traditional music performed by masters of their craft.

The government doesn't advertise this level of access. It's arranged through relationships built over years, often involving substantial contributions to preservation efforts and cultural initiatives.

The real difference

After years of witnessing how the ultra-wealthy vacation, I've realized something important. It's not just about money. It's about access to experiences that money alone can't buy. These people have created a parallel tourism industry that operates on relationships, referrals, and resources that go beyond writing a check.

But here's what my time in Thailand taught me, and what living in Austin with my simple 1920s bungalow reinforces daily: the most exclusive vacation in the world can't give you what a sunset beer with good friends can.

The ultra-wealthy might own islands, but they can't buy the feeling of contentment I found living in a small Bangkok apartment, making friends with the local coffee cart owner who gave me free biscuits.

I've kept one luxury item from my high-end hospitality days, a vintage Omega watch that sits on my wrist. It reminds me that I've seen both sides. I've organized dinners that cost more than houses and I've had meals at Thai street stalls that were infinitely more memorable.

The ultra-rich have turned vacationing into something unrecognizable to the rest of us. But after seeing it all up close, I'm pretty happy with my occasional trips to Mexico, staying in neighborhoods where the tacos are cheap and the hospitality is genuine.

Because real wealth? As I learned serving billionaires, it's not about the private island. It's about knowing you have enough.

And that vintage Omega? It tells the same time whether you're on a superyacht in Svalbard or sitting on your porch in East Austin. That's the only luxury that really matters.