Multigen Travel

Two insiders tell you where to go, what to do

BY ANDREW SESSA — Spring 2018

ot so long ago, “multigenerational travel” meant a vacation house that you and your extended family returned to from time to time, or perhaps a once-in-a-lifetime trip you took to celebrate a milestone such as a 50th anniversary or 75th birthday. These days, it’s something quite different. Large groups of relatives now travel together as often as once a year, if not twice, for lengthier periods, on more involved itineraries, and to different destinations each time. They seek out more immersive, authentic, and rich experiences, too, often in places as unexpected as they are exciting.

Today’s more active-minded and purpose-driven travelers now meet up with relatives in the most far-flung corners of the globe to kick off multistop trips that have them getting under the skin of each place they visit. They might connect with local artists to explore Cuban paintings, then create works of their own. Or they’ll volunteer on Central American philanthropic projects, helping to build a playground; or spend a day at a Southeast Asian school, attending classes and playing soccer with students the same age as kids in their own family. They delve into wildlife conservation when on safari in Africa or while cruising the Galapagos, or even trace their lineage on trips back to ancestral homelands.

Multigenerational travel as we now know it got its start more than 15 years ago, but it has changed dramatically and expanded exponentially since then, especially for the most affluent of vacationers. In the last eight years, it has been the No. 1 trend in the annual “Luxe Report” produced by Virtuoso — a leading consortium of luxury travel advisers and agencies — all but once, and even then it only fell to the No. 2 slot. It certainly appeals to current key desires the wealthiest of travelers have for trips that offer deep meaning, interpersonal connections, a strong sense of authenticity, and true individualization, among other elements. Today, travel and hospitality companies of all varieties have adapted and developed their offerings to meet these wishes, and meet them well.

“I think it all started to blossom after 9/11,” says Virtuoso travel adviser Jack Ezon, president of Ovation Vacations in New York, which books upward of 200 multigenerational trips a year. “There was a change in the tide, and people started to bring their kids everywhere. Time and family started to feel a lot more precious.”

Kimberly Wilson Wetty, co-owner and co-president of the eponymous New York-based Virtuoso travel agency founded by her mother, Valerie Wilson, agrees that 9/11 was a turning point, noting that it triggered a shift from valuing possessions to valuing something much weightier: “Travel became less about purchasing material goods,” says Wilson Wetty, whose firm also books hundreds of multigenerational journeys a year, “and more about accumulating experiences.”

The Great Recession caused the wealthy to put even greater emphasis on experiences, leading them to limit conspicuous consumption and increase expenditure on more meaningful interactions and adventures. All this has gone on while baby boomers enter their golden years as the largest and, importantly, most active generation to ever hit retirement. They’re 65 and 70 years young and looking ahead to decades’ more worth of quality time with their families. “They have disposable income and want to connect with their kids and grandchildren in a way previous generations didn’t,” says Wilson Wetty. “That’s created a real focus on multigen travel recently.”

With folks more spread out around the country — and around the world — than ever before, Sunday family dinners at grandma’s have become a thing of the past, and thanks to our obsession with the screens in our hands and at our desks, our digitally focused days leave each of us in our own little atomized worlds. These factors, too, have made multigenerational travel increasingly of the moment: People see these trips as unique and vital times to unplug from technology and reconnect with the most important people in their lives.

“It’s one of the few ways that families can really engage with and see each other these days,” concludes Wilson Wetty. “That’s why these holidays are becoming more frequent, longer, and more elaborate, as well as more meaningful” — and why multigenerational travel shows no sign of slowing down anytime soon.

Staying on Trend

What’s new in multigenerational travel? Ezon and Wilson Wetty tip you off to some of the latest developments in a quartet of core categories.


Hotels and resorts cater to family groups in two key ways right now: They build accommodations for them, and they create experiences on property and off to interest all ages. In Antigua, Jumby Bay Island recently unveiled its seven-bedroom Pure Turquoise beachfront estate, which Ezon likes for its tennis court, pool, and beach; Turks & Caicos’ Grace Bay Club, meanwhile, has new villas designed by Thom Filicia; and Four Seasons launched a private island in the Maldives called Voavah at Baa Atoll that sleeps 22 people. Hotels have created special suites and blocks of rooms that connect, too, such as the Ritz-Carlton, Grand Cayman’s 2-year-old penthouse that can be combined with other rooms to create a 20,000-square-foot space.

That Ritz also excels in designing experiences, Ezon says, thanks to its Ambassadors of the Environment program, in which kids of all ages can get up close and personal with Caribbean sea life. Wilson Wetty points to Dorchester Collection, which has developed beach picnics with food by Wolfgang Puck at its Hotel Bel-Air in LA and truffle-hunting adventures at its Hotel Principe di Savoia in Milan, among many other excursions beyond the hotel. Just last summer, Auberge Resorts Collection started a slate of family activities that range from stomping grapes into a personal wine blend at Napa Valley’s Calistoga Ranch to horseback riding with a local cowboy at Costa Rica’s Hacienda AltaGracia.


Villas prove perennially popular when large groups gather, but Wilson Wetty says requests for them have “exploded over the last few years,” going on to note that, “in terms of that full-immersion experience, a house can make you feel like you’re more of a local, because you’re going to the bakery, the fish market, the vegetable stand.”

Ezon says people don’t just want private houses these days, but their own private islands. Consider Thailand’s just-opened 10-acre Koh Rang Noi, that’s now available through John B. Sutherland, which offers 19 bedrooms in three newly built villas. 

Hiking to a fishing spot at Deplar Farm in Iceland. PHOTO BY DEPLAR FARMS.

Other travelers look to take over entire estates, such as the ever-expanding number of Scottish castles and manors now available as holiday homes exclusively through the recently launched Edinburgh-based travel outfitter Ossian. Several years back, Eleven Experience premiered with this idea in mind, opening small, full-service properties — including 2016’s Bahama House on Harbour Island and Deplar Farm in northern Iceland — designed for exclusive use. (They can now also be rented room-by-room but still suit multigenerational groups well.) Last fall, the travel company Red Savannah inaugurated its Private Estates concept, which consists of a collection of larger, fully staffed villas in prime locations, including a 10-bedroom Menorcan property, Binicalaf, which comes with its own sailboat.


Of late, cruise companies have put a focus on cabins for larger groups, including those on Holland America’s MS Koningsdam, which can sleep up to five. Royal Caribbean’s Symphony of the Seas will make its maiden voyage in April with a two-level Ultimate Family Suite, sleeping up to eight and featuring its own cinema, bumper pool table, and in-room slide.

Photographing sea lions in the Galapagos. PHOTO BY STEWART COHEN/LINDBLAD.

Active, adventurous destinations such as Alaska, Antarctica, and the Galapagos can prove especially popular for these sorts of trips, and cruise lines have created family programming just for these areas. Lindblad launched its National Geographic Global Explorers offering in the Galapagos last June to help families get the most out of the wildlife-filled islands, and Seabourn’s 3-year-old expert-led Ventures put guests on coast-hugging zodiacs and kayaks in Alaska and Antarctica.

Capitalizing on the current trend for tracing genealogy — something that many families are planning trips around — Cunard will offer a sailing in November in association with with four genealogists onboard.


When it comes to river cruising, Wilson Wetty says that AmaWaterways’ partnerships with Adventures by Disney and the biking, hiking, and walking outfit Backroads on certain sailings have done much to make river cruising more appealing to passengers younger than those often found on journeys down the Danube. Ezon notes that smaller river ships, such as the Aqua Mekong and the Belmond Road to Mandalay, both in Southeast Asia, are great for multigen trips because you can take over the whole vessel with relative ease.


As for safari offerings for multigen travelers, it’s increasingly all about exclusive-use camps and lodges. Singita — which has long had a wide range of specialized, customizable family-friendly fare — debuted its Singita Private offerings at the end of 2016 to help guests easily link stays at the recently renovated private villas at several of its properties. These included the four-suite Serengeti House at Singita Grumeti in Tanzania, which now features an eat-in kitchen, outdoor living room, and tented spa suite. Groups in these accommodations get their own driver-guides and vehicles for the length of their stay, giving them the freedom to fully tailor the game-viewing, wildlife-tracking experience.

The folks at Micato Safaris have seen a rapid rise in requests for lodgings like these. Beyond Singita, they favor the updated two-bedroom tent at Sala’s Camp in Kenya’s Maasai Mara and, from the same owners, a relatively recently added wing — with two new rooms added last June — at Giraffe Manor, on the outskirts of Nairobi, that’s ideal for families to take over. Kenya’s 4-year-old Ol Jogi Wildlife Conservancy, where Micato managing director Dennis Pinto stayed with three generations of his own family last summer, might well be the ultimate exclusive-use safari property, comprising 58,000 acres you and your crew will have all to yourself.

Related Stories

Ten tips from our two experts that will help make your next multigenerational trip an unequivocal success


both top Virtuoso
travel advisers

Jack Ezon and his team at Ovation Vacations book nearly 200 multigen trips a year.

At Valerie Wilson Travel, Kimberly Wilson Wetty and her team also book hundreds of these trips each year.


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