Ask Robb: I Want to Go on a Round-the-World Journey—but Where Should I Start?

Welcome to Ask Robb. At Robb Report, we’ve assembled a crack team of the world’s best travel specialists, our Travel Masters. Their expertise and insight in luxury travel of all kinds is unparalleled. So we’re tapping into it directly for a new series, where our readers—that’s you—pose the pickiest travel problems to the panel. These aren’t workaday issues, whether wrangling a refund or booking a guide, but rather the unique, specific challenges that only veteran globetrotters face.

Dear Robb Report: I want to take a round-the-world trip—perhaps not in 80 days, but whatever it takes. What are my options by air and sea, and what would you recommend? What prep should I make for this kind of journey? Yours, Flighty Phileas

It’s not surprising you’re interested in this idea, as the air cruise industry has made these jaunts more accessible than ever. Companies like TCS World Travel, Four Seasons and Safrans du Monde all operate round-the-world itineraries in charter jets that whisk a small group of well-heeled, jet-lag-fighting travelers round the globe at a breakneck pace, usually around three weeks or so.  The real luxury, though, lies in planning one that’s entirely private and personalized, so you don’t ever risk a dull bus tour or a delayed departure thanks to an always-late couple.

Jules Maury of Scott Dunn Private spent a year sailing the high seas herself, bouncing from island to island, so she understands the yearning to circumnavigate the globe at your own pace and to your exact preference. When she’s been tapped to plan such trips for clients, her first question is simple: Where are the must-see destinations? She’ll then suggest the time of year when a client should kick off their trip.

“You can’t go round the world in the same season—you have two hemispheres that are so different,” she explains.

In summertime, for example, northern Australia and Bali are beautiful and it’s peak safari season, too. Tokyo, though, will be clammy and muggy, while India’s temperatures will make much sightseeing impractical. If Japan’s a priority, she’d recommend delaying departure until the fall, though that will likely mean a trade-off in the South Pacific where wet season there starts in November.

One option, of course, is to follow the lead of one Scott Dunn Private client, who simply booked two round-the-worlders, departing months apart, so he could see everywhere at its peak season. Each trip took between 33 and 42 nights. Traveling as a couple, he paid $300,000 but scored some airfare bargains by booking ahead on the other trip, and cut his costs to $225,000. These are longer itineraries than the commercially operated air cruises, and for good reason.

“It’s critical to tell people they can’t do it too fast,” Maury warns. “Or you’ll get exhausted, or bored, or just want to go home.”

Build in buffer time, too, in case of sickness—using a travel specialist, of course, means you can turn to them to rejigger should you fall ill. Don’t forget logistics, either: time to turnaround laundry, for example. “You have to pace it,” says Maury.

Christopher Wilmot-Sitwell of Cazenove & Loyd agrees. Take a moment to consider whether or not you even want to circumnavigate the world in a single trip, he suggests. He worked with one client who wanted to follow the footsteps of an ancestor, an 18th-century sea captain.

“He wanted to take his family to all the places this chap had been to, on the amazing voyage he did. But there was not a way of doing that in a normal way, if you don’t want to take a year out of your life,” Wilmot-Sitwel says. Instead, the client broke up the journey into short trips over a 12-month period, covering four different continents. It was a round-the-world trip, carved into bite-sized pieces.

He also emphasizes that it’s important to consider the modes of transport. Sure, you can fly almost anywhere, but sometimes it’s better to take a train to see the countryside or a boat to experience the thrill of docking in a remote location. That ancestry-obsessed client, for instance, combined a charter plane, helicopter, and yacht on one leg, tapping an historian to join at each juncture.

“All of the locations were so out of the beaten path of scheduled flights that this was the only way to achieve it,” says Wilmot-Sitwell.

Maury concurs. Don’t assume that a private charter for the entire trip is the best option. A Gulfstream 650 isn’t particularly comfortable for long-haul trips, especially compared to, say, the first class cabin on Emirates.

“It’s not that comfortable to charter round the world, and not all the airports where you’re going will have the greatest engineers,” she notes, pointing out that delays can occur when a private plane malfunctions in the middle of nowhere.

To offset the commercial components, Maury has worked in sea planes and the Eastern Orient Express, among others, into such itineraries, in part because the romance of the journey is often at the root of why anyone plans such a trip.

“It’s that nostalgic Phileas Fogg instinct, like going back in time,” she says. “It’s like imagining an old-fashioned globe with passport stamps all over it.”

If you do plan that trip, Flighty Phileas, just make sure to send us a postcard.