Rebecca Engel
Some trips you just book. Others you build towards, putting a bit away every month for a year or two until the thing that seemed silly starts to look possible. This list is the second kind.
These are luxury travel destinations that earn the saving, which is a different test from simply being expensive. Plenty of places will happily take a lot of money off you and hand back a nice room. The twenty one here give you something you can’t get at any other price, whether that’s a house reef outside your door, a tent in the middle of a migration, or a boat to somewhere almost nobody goes.
1. The Maldives
Nearly twelve hundred islands scattered across twenty six atolls, and the thing that makes the Maldives what it is has nothing to do with the water. It’s the one resort per island rule.
You aren’t staying at a hotel on a beach. You’re staying on the whole island, and there is nobody else on it. That’s what the money buys, along with an overwater villa with a ladder straight down into the lagoon and a house reef you can snorkel from your own steps.
Getting there is part of the cost. Most resorts are a seaplane hop from Malé and that transfer lands as a real line item on top of everything else. The dry season runs November to April.
2. Bora Bora, French Polynesia
The overwater bungalow was invented here, and not for the reason you’d guess. In 1967 three American hotel owners on the island of Raiatea had a plot with a road on one side, the sea on the other and almost no beach to build on, so they put the huts out over the water instead.
They cut windows into the floors and called it Tahitian TV. Marlon Brando checked in almost immediately and the idea spread to everywhere warm enough to copy it.
Bora Bora is where it grew up. A lagoon running through about six shades of blue with Mount Otemanu standing in the middle, and enough space between resorts that you rarely see another one. Fly through Tahiti and go May to October.
3. Santorini, Greece
Santorini is the rim of a volcano that blew its middle out, which is why the island curves the way it does and why the hotels are stacked down the inside of a cliff.
The rooms are the attraction here. Cave suites cut back into the rock with private plunge pools hanging over a nine hundred foot drop, all pointed the same way for the same reason.
The mistake is going in August. Cruise ships unload into Oia in the middle of the day and the lanes become impassable. May, June and late September give you the same view with room to stand in it.
4. The Amalfi Coast, Italy
Forty miles of cliff with towns wedged into it wherever the rock allowed. Positano pours down towards the water in stacked pastel, Ravello sits high above with gardens looking along the whole coast, and the road between them is famous for being terrifying.
The luxury here is old rather than new. Converted monasteries and cliffside hotels that have been taking guests for more than a century, most with a lift cut down through the rock to a swimming platform.
Hire a boat for a day. The coast was built to be seen from the water and it’s the one thing that makes the traffic on the road irrelevant. May or September.
5. Dubai, United Arab Emirates
Dubai does one thing better than anywhere, and that thing is scale. The Burj Khalifa is a little over 2,700 feet tall, roughly twice the Empire State Building, and it isn’t even the point.
The point is that the city treats service as a competitive sport. Suites in sail shaped hotels on their own island, and restaurants run by chefs who moved here because this is where the budget went.
An hour outside, the desert does the opposite. Private camps in the dunes with nothing around them at all. Go November to March, because summer here sits well above a hundred degrees.
6. Lake Como, Italy
Como is a lake shaped like an upside down Y with the Alps standing at the top of it, and people with money have been building on its shores since the Romans. That’s a long time for a place to get good at this.
The grand old villa hotels are the reason to come. Nineteenth century buildings with terraced gardens running down to the water, swimming pools floating just off the shore, and boats that collect you from the steps.
Bellagio sits where the three arms meet and gets most of the attention. Varenna across the water is quieter and nicer to stay in. April to October, and the shoulder months are far calmer.
7. The Seychelles
A hundred and fifteen islands sitting on their own in the Indian Ocean, and what separates them from every other tropical destination is the rock. Enormous smooth granite boulders sit right on the sand, worn into shapes that look deliberate.
Anse Source d’Argent on La Digue is the beach everyone photographs and it holds up in person. Praslin has a palm forest called the Vallée de Mai, a world heritage site full of a nut that grows nowhere else.
Resorts run small and spread out here. It’s a quieter, more barefoot luxury than the Maldives and it’s much easier to move between islands. April, May, October and November are the calmest months.
8. Bali, Indonesia
Bali is two luxury destinations at once and they look nothing alike. In Ubud it’s jungle, with villas built into the valley sides and infinity pools hanging out over the trees.
On the southern cliffs at Uluwatu it’s the opposite. White stone, open air, and a straight drop to the ocean below. Same island, an hour apart.
It’s also by some distance the cheapest place on this list for the standard of villa you get, which is a large part of why it’s here. April to October is the dry season.
9. The Okavango Delta, Botswana
A river that never reaches the sea. The Okavango runs down out of Angola and empties into the Kalahari, spreading into a delta in the middle of a desert, which is as odd as it sounds.
The strangest part is the timing. The flood arrives during the dry season, so the water peaks around June to October, exactly when everything else has dried up and the animals come to it.
Botswana deliberately keeps visitor numbers low and prices high, and the money goes into conservation. What you get is a camp with a handful of tents, no fences, and a dugout canoe called a mokoro poled through the channels at eye level with everything in them.
10. Kyoto, Japan
Kyoto is on this list for one thing in particular, and that’s the ryokan. A traditional inn with tatami floors, a private cypress bath and a multi course kaiseki dinner brought to your room by someone who has been doing it for thirty years.
The best of them have been run by the same family for generations and take a handful of guests a night. It’s the least flashy luxury here and probably the most memorable.
Book a long way ahead for April and November, which are blossom and autumn colour and the two windows everybody wants. The rest of the year is far easier and still beautiful.
11. St Barths, French West Indies
Eight square miles of French Caribbean, reached by a short hop from St Martin onto one of the more alarming runways in the hemisphere. The approach comes over a hill and drops onto the strip.
What separates it from the rest of the Caribbean is that it is genuinely French. The food is French, the shops are French, and there are no large resorts, because the island doesn’t permit them.
You rent a villa instead. High season runs December to April and the holidays are chaos, so the weeks on either side are the smart booking.
12. Aspen, Colorado
Four separate mountains on one lift ticket, an old silver mining town sitting at the bottom of them, and a main street carrying more fur than most cities.
Skiing is the headline and Aspen Highlands is where the serious version lives, with a bowl you have to hike to reach. But the town is why people come back, and it works just as well in summer when the wildflowers are out and everything costs less.
Book absurdly early for Christmas and the weeks around it. That’s when the town is at its most extreme in both directions.
13. Maui, Hawaii
Maui does luxury without asking you to fly halfway around the world, which counts for something. Wailea on the south shore and Kapalua in the northwest are where the good resorts sit, and both look straight out at other islands.
The island earns its place with what’s beyond the resort. Haleakala rises over ten thousand feet and the sunrise from the summit needs a reservation and a warm coat. The Road to Hana is a full day of waterfalls and one lane bridges.
It’s the easiest place here to combine a resort week with something more active. Peak season is winter, when the humpbacks are in the channel between the islands.
14. Courchevel, France
Courchevel sits inside the Three Valleys, the largest linked ski area in the world, which means you can ski for a week straight without repeating yourself.
The top village, known as 1850, is where the money is. Chalets that come with staff, a private altiport where small planes land on a sloped runway, and a cluster of Michelin starred restaurants that would be remarkable at sea level, let alone at altitude.
The season runs December to April. February is school holidays across Europe and the prices know it, so January and late March give you the same snow for less.
15. Marrakech, Morocco
The luxury here is behind a door in a wall. Riads are old houses built around a central courtyard, and from the lane outside they look like nothing at all. Inside there’s a fountain, a garden and a roof terrace.
The medina is loud and relentless and the riad is the counterweight to it, which is the entire point of the design. Jemaa el-Fnaa fills with food stalls and crowds after dark a few minutes’ walk away.
Camps out in the Agafay desert give you a second night somewhere completely silent. Spring and autumn are the seasons to aim for. Summer is brutal.
16. The Serengeti, Tanzania
Somewhere between one and a half and two million wildebeest move around this ecosystem in a slow loop, and the entire luxury safari industry here is built around putting you in the right part of it.
Calving season runs January to March in the south, when the plains fill with newborns and everything that hunts them. The river crossings people picture happen further north, roughly July to October.
The best camps move with the herds. Canvas, a handful of tents, taken down and rebuilt somewhere else a few times a year. Booking a year out is completely normal.
17. Queenstown, New Zealand
Queenstown sits on a lake with a mountain range behind it called the Remarkables, which is a name that only works if the place delivers. It does.
Luxury here means lodges rather than hotels. A handful of rooms, a lot of glass, a chef, and a helicopter pad, because much of what you’d want to do involves flying somewhere first. Heli skiing in winter, glacier landings and Milford Sound in summer.
It’s a long way from almost everywhere, and that’s the real cost. Once you’re in New Zealand, though, it’s the obvious place to spend the splurge part of the trip.
18. Antarctica
The most expensive thing on this list and the least like a holiday. You sail from Ushuaia at the bottom of Argentina, cross the Drake Passage for two days, and arrive somewhere with no permanent human population at all.
Ships are small because landings are limited by rule, so you travel with a hundred or so people rather than a few thousand. The season is short, November to March, and that’s the whole window.
What you’re paying for is a place almost nobody goes. Penguin colonies, ice the size of buildings, and a silence that people struggle to describe afterwards. If a list of destinations worth saving up for means anything, this is the one it was written for.
19. Singapore
Singapore decided at some point to be excellent at hospitality and then simply was. The service standard across the whole city is higher than almost anywhere, at every price level.
The famous version is a hotel with a ship on the roof and an infinity pool fifty seven floors up, and it earns the attention. The older version is Raffles, a colonial hotel restored to within an inch of its life.
The food is the sleeper reason to come. There are hawker stalls here with Michelin stars where lunch costs less than a coffee, and you can eat like that all week between the expensive dinners. It works year round.
20. Monaco
Less than a square mile, most of it built vertically, and more concentrated money per square foot than anywhere on earth.
The Monte Carlo end is the picture everyone has. A casino from 1863 that you have to dress for, a hotel across the square that’s older than the casino, and a harbour full of boats worth more than most streets.
Come in May if you want the Grand Prix and don’t mind paying several times over for it. Come any other summer month if you’d rather watch the place breathe.
21. Napa Valley, California
Thirty miles of valley floor carrying something like four hundred wineries, and a hospitality scene that grew up right alongside them.
The good hotels sit up on the hillsides looking down the valley, with a terrace, a long lunch and very little else scheduled. That’s the correct way to use Napa.
Tastings are by appointment at most places worth visiting, so this is a trip that needs a little planning. Harvest runs August through October and is the best time to be there, and also the busiest.
More Luxury Travel Destinations Worth Considering
A few that didn’t make the twenty one but would on a different day.
Patagonia gives you something close to the Antarctica feeling for a fraction of the cost, with lodges in Torres del Paine looking straight at the towers. Bhutan limits visitor numbers by design and charges a daily fee that goes back into the country, which makes it one of the least crowded places you can go.
Turks and Caicos has the best beach in the Caribbean by most counts and is a far shorter flight than the Indian Ocean. Provence in early summer is lavender, hilltop villages and old farmhouses done properly.
And the winelands outside Cape Town do roughly what Napa does at about half the price, with mountains standing behind them.
How To Do A Luxury Trip For Less
None of this is cheap. But the gap between high and low season at the same property is often enormous, and the weather difference is usually small.
Shoulder season is the single biggest lever you have. Santorini in late September, the Maldives in May, Aspen in March. You’re frequently paying half for the same room.
Fewer nights somewhere better beats more nights somewhere worse, and it’s the trade most people get backwards. Four nights somewhere genuinely special is a better trip than ten somewhere fine.
Points and miles are worth learning if this is a once every few years thing, because a long haul business class seat booked with points is usually the largest single saving available. And always ask what’s included, since a rate that looks higher often covers transfers, meals and drinks that would otherwise land as a few hundred extra a day.
Final Thoughts
The common thread across these luxury travel destinations isn’t the thread count. It’s that every one of them gives you something the money is genuinely buying rather than just decorating.
An island with nobody else on it. A camp that moves with the animals. A boat to somewhere almost no one has been. Those are the trips people are still talking about decades later, and none of them are improved by a bigger television.
So pick one and start putting it aside. The saving is the easy part once you know exactly what it’s for.
