Every once in a while someone asks me a question I love answering.

“What’s the most amazing trip you can take if money doesn’t matter?”

If a client came to me and said, “I want the most extraordinary trip possible,” these are the kinds of trips I would start talking about.

Four Seasons or TCS World Travel Private Jet Journeys

Private-jet journeys are about seeing an astonishing amount of the world in a short time.

Companies like Four Seasons and TCS World Travel have built entire itineraries around this idea. Instead of navigating airports and layovers, you travel on a beautifully outfitted private aircraft with a small group of guests and a team dedicated entirely to your journey.

One morning you might be exploring temples in Kyoto. A few days later you could be walking through Petra at sunrise. Before long you’re heading out on safari in East Africa.

The entire experience is designed to remove the friction from travel and replace it with something seamless and highly choreographed. It’s less about transportation and more about creating a temporary world where everything simply works. Ready to book? Book a complimentary vacation consultation here.

Aman Private Jet Expedition

For a certain kind of traveler, Aman’s private jet journeys may be even more appealing than the traditional around-the-world itineraries.

Aman has built a reputation for understated luxury and extraordinary design, and their jet expeditions connect some of their most iconic properties. The journey might begin in Tokyo, continue along Vietnam’s dramatic coastline, move on to Angkor Wat in Cambodia, and finish in the Himalayan valleys of Bhutan.

The common thread is Aman’s philosophy of calm, space, and deeply attentive service. These trips tend to attract travelers who already know the brand well and want to experience several of its most remarkable destinations in a single, seamless journey.

It’s a quieter kind of luxury, but no less extraordinary.

The Ultimate African Safari

Africa can become wildly luxurious very quickly when it’s done properly.

A top-tier safari might include a series of small camps across Kenya or Tanzania, each reached by private aircraft so that your time is spent watching wildlife rather than sitting in vehicles. One part of the trip might focus on the Great Migration, while another explores remote landscapes where you see almost no other visitors.

Many travelers add gorilla trekking in Rwanda or Uganda before ending the journey somewhere warm and beautiful like the Seychelles or Zanzibar.

What makes a safari so magical isn’t just the animals. It’s the feeling that you are somewhere profoundly wild while still being incredibly comfortable. You might spend the day watching elephants cross the savanna and return in the evening to a beautifully prepared dinner and a quiet campfire under a sky filled with stars. Ready for your safari? Book a complimentary vacation consultation here.

A Belmond Barge Through Burgundy

Belmond operates a small fleet of elegant barges that glide through the canals of Burgundy and Champagne, carrying only a handful of guests at a time. The experience feels less like a cruise and more like staying in a beautifully designed floating country house.

Days unfold gently. You might cycle through vineyards in the morning, visit historic estates in the afternoon, and return to the barge for a long dinner prepared by the onboard chef while the scenery drifts slowly past.

Add a few nights in Paris before or after the journey and it becomes a wonderfully indulgent two-week exploration of France. This is honestly my dream trip right now.

The New Four Seasons Yacht

Four Seasons is entering the yachting world, and it’s shaping up to be one of the most interesting new offerings in luxury travel.

Unlike traditional cruise ships, the yacht is intentionally small, carrying fewer than a hundred suites. The scale feels closer to a private yacht than a cruise ship, but with the service and infrastructure of a luxury hotel brand behind it.

Suites are enormous, the design is sleek and contemporary, and the itineraries will focus on glamorous destinations across the Mediterranean and Caribbean. For travelers who love the romance of yachting but want the reliability of a luxury hotel brand, it’s likely to become a very compelling option. Ready to experience the new Four Seasons Yacht? Book a complimentary vacation consultation here.

Antarctica by Expedition Yacht

Another way to experience Antarctica is aboard one of the new ultra-luxury expedition ships.

Vessels like Scenic Eclipse and Silversea’s expedition fleet combine serious polar exploration with very refined accommodations. During the day guests head out by Zodiac boat to explore glaciers, ice formations, and wildlife that changes constantly with the conditions.

Evenings, however, feel very different from the rugged stereotype of polar travel. Guests return to excellent dinners, spacious suites, and lounges where the landscape outside the windows still looks almost unreal.

It’s Antarctica, but with a layer of comfort that makes the experience accessible to many more travelers.

A Luxury Galápagos Yacht Journey

The Galápagos Islands are famous for wildlife, but what many people don’t realize is that the luxury version of this trip can be extraordinary.

Small yachts carry just a handful of guests through the archipelago, allowing close encounters with animals that seem almost completely unafraid of humans. Sea lions nap on beaches, blue-footed boobies perform their elaborate courtship dances, and giant tortoises move slowly through the highlands.

In January, I experienced the Galapagos with Lindblad and National Geographic, which was incredible. But I’d call it more of a low 4 star trip when it comes to accomodations. More luxurious versions exist!

Bhutan at the Highest Level

Bhutan offers a completely different kind of luxury.

Instead of extravagance, the appeal here is serenity and landscape. A two-week journey through Bhutan might move between several lodges across the country, allowing travelers to experience its monasteries, mountain valleys, and deeply rooted traditions.

The pace is slower, the scenery dramatic, and the entire country has a feeling of intentional preservation. For travelers who have already seen much of the world and want something that feels meaningful rather than flashy, Bhutan can be profoundly moving.

Japan by Shinkansen and Ryokan

Most people think of Japan as accessible and relatively affordable. And for most travelers, it is.

But there is another version of Japan.

It begins in Tokyo, at one of the city's finest hotels — somewhere with a view of the Imperial Palace gardens and a restaurant that has held Michelin stars for years. From there, the journey moves by shinkansen through the Japanese countryside, arriving in Kyoto in time for an afternoon of unhurried temple visits with a private guide who has spent decades studying the city.

The accommodations, however, are what make this trip truly rare. The finest ryokans in Japan — places like Tawaraya in Kyoto or Beniya Mukayu in Yamanaka Onsen — are among the greatest hospitality experiences in the world. Rooms are spare and exquisite. Kaiseki dinners unfold over twelve courses, each one a small meditation on the season. The onsen is private, the service almost wordless in its attentiveness.

For travelers who want to go further, there is the Seven Stars in Kyushu — Japan's legendary luxury sleeper train, which winds through the island's volcanic landscapes and traditional villages in a way that feels entirely removed from modern life. Bookings are extraordinarily difficult to secure. Which, for certain travelers, is rather the point.

The Orient Express

The Venice Simplon-Orient-Express has been a byword for romantic rail travel for decades. But what's less widely known is that an entirely new chapter of luxury train travel is quietly unfolding across Europe.

New Orient Express trains are being launched across France and Italy — restored carriages, contemporary design, itineraries that move through countryside most travelers only ever see from an airplane window. The experience is less about speed and entirely about the journey itself. Long dinners in the restaurant car. Landscapes that change while you sleep. The particular pleasure of arriving somewhere feeling genuinely unhurried.

For a certain kind of traveler — one who finds airports exhausting and believes the journey should be as memorable as the destination — there is nothing quite like it.

India by Private Train or Plane

The Maharajas' Express is one of the great luxury train journeys in the world. It moves through Rajasthan — past forts and palaces and desert cities — stopping at the Taj Mahal at dawn, continuing to the ghats of Varanasi, where the city's ancient relationship with the river unfolds in a way that is unlike anywhere else on earth. The train itself is palatial. The service is extraordinary. And the window between cities becomes part of the experience rather than merely the means of getting there.

For travelers who want even more flexibility, a private aircraft journey covering the same highlights — with nights in actual former royal palaces converted into extraordinary hotels — offers a different kind of India entirely. Either way, it tends to be transformative. Travelers who come expecting spectacle often leave having been quietly moved by something they didn't anticipate.

Who doesn’t want to go to French Polynesia?

French Polynesia by Private Yacht

Bora Bora is the famous name. The overwater bungalow, the turquoise lagoon, the photograph that appears on roughly half of all honeymoon mood boards.

But the truly extraordinary version of French Polynesia is found further out — in the Tuamotu Archipelago, a scattered chain of low-lying atolls where the water is so clear and the marine life so abundant that divers travel from around the world specifically for what lies beneath the surface.

A private yacht charter through these islands — moving between anchorages that have no hotels, no infrastructure, and no other visitors — is one of the most genuinely remote luxury experiences available in the Pacific. Days are spent snorkeling over coral that appears entirely untouched. Evenings are spent on deck, in waters calm enough to reflect the stars.

It requires more planning than most trips. It is worth considerably more than most trips.

The Real Truth About the “Most Expensive Trip”

The funny thing about this question is that the most expensive trips are rarely the ones you see advertised.

Once you start combining private aviation, yacht charters, exclusive guides, and extraordinary accommodations, the ceiling rises very quickly. The most extravagant two-week journey is usually something designed entirely from scratch for a particular traveler.

Still, the trips above offer a glimpse of what is possible. They represent the outer edge of travel — rare places, remarkable logistics, and experiences that are difficult to replicate any other way.

And for people who love exploring the world, it’s hard not to find that idea a little thrilling.

If any of these made you lean forward in your chair a little, I'd love to know which one. Hit reply and tell me — I'm always curious which destinations stop people in their tracks. And if you want to start talking about turning any of these into an actual itinerary, that's exactly the kind of conversation I enjoy most. Book a complimentary vacation consultation here.

— Krista

About Krista

I’m a Virtuoso travel advisor based in Palm Beach, Florida. I attended the University of Notre Dame for undergrad and I have my MBA from the University of Chicago. Before building my travel business, I spent 20 years in the investment management industry and over a decade living and working in London, England. I’ve personally traveled to 80 countries and now design thoughtful, highly customized trips for travelers who value expertise, access, and a seamless experience.

I offer a complimentary 30-minute consultation for travelers considering a custom itinerary or luxury cruise. Book a complimentary vacation consultation here.

For travel inspiration and real-time updates, you can follow along on Instagram or connect with me on Facebook. I also share a curated list of travel products I genuinely use and recommend in my online store.

What I Offer…

Custom itinerary design for complex, multi-stop trips
VIP hotel benefits through Virtuoso and preferred partner programs (including complimentary breakfast, hotel credits, and priority for upgrades where available)
Luxury ocean, river, and expedition cruises with added onboard credits
Vetted villa rentals with concierge services worldwide
Private guides, small-group touring, and unique local experiences
Private aviation and yacht charters through trusted partners
Airport transfers, VIP arrival and departure services, and full ground logistics
Travel protection and support when plans change

I work best with travelers who want expert planning, trusted partnerships, and someone in their corner from start to finish. That’s what I am best at! Ready to talk travel? Book a complimentary vacation consultation here.

The Most Over-the-Top Trips You Can Take