Staggering, right? The world’s most expensive holidays cost more than most Toronto homes. And we’re not talking about splurging on a penthouse in New York. We’re talking week-long getaways that could swallow your life savings whole. These aren’t your run-of-the-mill beach breaks with poolside cocktail service. We’re stepping into a universe where travel becomes jaw-dropping extravagance – think private islands, onboard chefs, diamond-encrusted hotel suites, and experiences so rare you’ll barely believe they exist. Curious what drops jaws wide open on the vacation price scale? Let’s break down why some holidays end up rivaling private jets in price tags, what exactly you get for your millions, who books these legendary trips, and most importantly, how you can snag even a taste of this high-flying luxury (without selling your condo).
The Most Expensive Holiday Experiences on Earth
First, let’s shine a light on trips that set the record for jaw-dropping price tags. The name “most expensive holiday” goes to a rotating cast, but a few contenders keep coming up every year thanks to travel agents who cater to ultra-high-net-worth folks. Top of the list: a $13 million, two-year, 150-country jaunt on a luxury private jet, organized by DreamMaker. This journey isn’t just about sights; it comes with a private chef, a medical team, and even a personal photographer. Imagine taking off from London, sipping 30-year-old Macallan as you fly over the Mongolian steppe, your every whim catered to before you land in Bhutan for a private blessing from monks.
Another serious contender: renting Calivigny Island, just off Grenada, for $140,000 a night. We’re talking 80,000 tropical square feet, only accessible by private yacht or helicopter. You get a staff of 85 on hand, including Michelin-star chefs, for you and just 49 guests. If dropping $980,000 for a week on a private island sounds wild, remember this: past guests have included movie stars looking for privacy and peace, away from the paparazzi’s choppers in St. Barts.
If you want something wilder, Abercrombie & Kent offers a 25-day Arctic and Antarctic adventure for $2.1 million, with only 12 seats. The kicker? It’s all by private jet, and includes polar bear safaris, whale-watching in Antarctica from a heated deck, and even lunch with scientists at a polar research station. Ever heard of the Royal Penthouse Suite at the Hotel President Wilson in Geneva? $80,000 a night. It takes up the entire top floor, 12 bedrooms, a Steinway grand piano, bulletproof windows, and a view of Lake Geneva you won’t find on postcards.
Where Do Rich People Go? Ultra-Exclusive Destinations
When you look at lists made by travel experts in 2024, it’s places like Musha Cay (Bahamas), Necker Island (Richard Branson’s slice of paradise), and Laucala Island (Fiji) topping the ultra-expensive heap. These private islands are decked out with everything; think open-air cinemas, underwater wine cellars, and fleets of speedboats ready at your call. Renting Laucala, for example, is about $150,000 a night, but you get total run of 25 overwater villas, a private golf course, and meals whipped up by world-renowned chefs. No tourists, no trek lines, no strangers hogging the pool chairs.
Diving deeper into city escapes, the Burj Al Arab’s Royal Suite in Dubai clocks in around $30,000 a night—with your own butler, driver, and private elevator. Paris? Suite Belle Etoile at Le Meurice draws similar prices, with its heated rooftop Jacuzzi and 360-degree views of the City of Light. For winter escapes, Igloo Village in Zermatt, Switzerland, lets you sleep under the stars, cozy in heated fur-draped ice-suites, for around $10,000 a night, complete with private chef-prepared fondue dinners and dog-sled rides at dawn.
Let’s not overlook “destination events,” either. Super-rich folks sometimes buy out entire small resorts for wedding weeks, milestone birthdays, or even group meditation retreats. In 2023, an anonymous Silicon Valley billionaire rented every villa in Maldives’ Cheval Blanc Randheli for his 40th birthday—bringing friends, Michelin chefs, live concerts, and even rare blue lobsters flown in from France.
What You Actually Get For the Money
Sure, some of the price is about location, but much of the sticker shock comes from how customized the experience is. When you fork out $1 million or more on a trip, you’re not just booking better seats or fancier meals. Every second gets tailored—sometimes right down to the brand of soap in your ensuite. If you want a sunrise yoga session on a platform built in a rainforest canopy or a dinner hosted by a Michelin-starred chef on a sandbar only accessible by seaplane, you get it.
24/7 staff is the norm at this level, not a perk. These holidays often include private tutors for kids, personal trainers, on-call physios, sommeliers, yacht captains, and dedicated guides with PhDs in art history or zoology to enhance excursions. The food is outrageously good and always personalized. Fancy eggs Benedict at 4 a.m.? Not a problem. Guests also get “insider” access: private tours of museums after hours, dinners with local royalty, personalized shopping at closed salons, and helicopter rights to skip lines or reach spots regular tourists never see.
Security and privacy are top priorities too. These places often run background checks on staff, block airspace to keep paparazzi at bay, and can even arrange for decoy vehicles so guests never attract attention when stepping out. Did I mention customized menus for your pets, or private doctors who fly in for routine checkups? You can see why a week racks up costs faster than a Toronto Raptors courtside seat.
Why Are These Holidays So Expensive?
The cost isn’t just about gold taps and white-glove service. These trips often involve rare experiences or nearly impossible access. Take space tourism. Both SpaceX and Blue Origin are now offering civilian seats for sub-orbital flights: Virgin Galactic’s standard ticket price as of 2025 is $450,000 per seat, a figure that doesn’t even include custom astronaut training or pre-launch consultations with nutritionists and psychologists. Jeff Bezos himself greeted the world’s first all-civilian crew on Blue Origin’s capsule in August 2022—talk about bragging rights. If you want a seat on Elon Musk’s longer “dearMoon” lunar flyby scheduled for 2027, you’re shelling out millions, most via invitation only.
Back on Earth, another reason for the ballooning costs is sheer demand. There are only so many private islands or medieval castles for rent. When the world’s one percent want in, prices shoot up. Luxury travel companies like Black Tomato and Red Savannah have built entire businesses around discretion and personalization. In a pandemic or other crisis, these providers can deliver emergency extraction. This kind of flexibility adds huge value for buyers who want certainty over everything—weather, safety, food, and privacy.
Some of it really is just keeping up with the Joneses. In elite circles, bragging about “exclusivity” is part of the draw. Did you get flown to a glacier in Patagonia via private chopper and have ceviche while watching the sun set over a mirror lake? The ‘rare factor’ is a huge deal among those who can already afford every car and villa on Earth. And yes, a solid chunk of the fee is about peace of mind: knowing there’s a private medic, a disaster plan, and top-tier security if anything goes sideways.
Tips for Experiencing Luxury Without the Billionaire Price Tag
Here’s where it gets fun. Want a slice of that bling without remortgaging everything? There are a few sneaky ways to get a taste of the high-life. First up: timing. Most five-star resorts have “shoulder seasons” (just before or after peak), where $8,000 suites drop to $800. Yes, staff is still world-class. In places like the Maldives, Seychelles, or St. Lucia, off-peak bookings can cut rates by more than half.
Some luxury travel agencies run “empty leg” deals for private jets or yacht charters that need to reposition. You can snag a spot on a $50,000 jet flight for under $5,000 if your schedule is flexible. That’s how a few clever Torontonians I know have surprised loved ones with experiences usually reserved for celebrities. And don’t forget credit card rewards: the right card with a hefty sign-up bonus can land you nights at suites in Singapore’s Marina Bay Sands or New York’s Plaza Hotel—if you’re disciplined about spending and points hacks.
A different hack? Look for “day passes” at elite resorts or beach clubs—even if you can’t swing the $10,000-a-night villa, you can sip champagne by the infinity pool for the day, rub shoulders with the elite, and get that Instagram shot. Web forums (like FlyerTalk and Luxury Travel Diary) sometimes highlight “error fares” and rare deals, so sign up for fare alerts and keep your passport handy.
Want a taste of unique luxury? Some countries offer bespoke experiences without the full billionaire markup. Portugal has boutique vineyard hotels with personal chefs, while in Thailand, you’ll find private island glamping for under $400 a night, complete with butler service. Book far in advance—sometimes even a year—before rates go up, and always ask about free upgrades or extra perks. The travel world loves loyal customers, and a simple ask can land a bottle of champagne or even a one-off spa upgrade.
Truth is, spending like a billionaire on holiday is wild—and rare. But with a little research, you can experience slivers of their world without going broke. Most expensive holiday doesn’t have to mean “out of reach forever.” Sometimes, it’s mostly about knowing where—and when—to look.