Multigenerational travel has been the biggest trend in tourism for more than five years. Now it’s changing the configuration of resort and second-home destinations as the wealthy demand ever-larger lodgings to accommodate extended families and friends—and sometimes, entire communities.

By Dianna Carr

Among the many revelations of our Future of Luxury Travel Report, our study of the top 1% and 5% of the wealthiest U.S. travelers released last fall, was the fact that America’s most affluent globetrotters not only go to more places in more ways than other travelers, they want everyone to come with them. Forty-five percent of the top 1% (those surveyed with household incomes of $400k+ and/or a net worth of $8 million+) want to vacation with friends—even more than they want to take a family vacation with kids (41%).

And 30% want to take a multigenerational vacation, all in numbers significantly higher than total U.S. travelers. But to accommodate these new luxury holiday tribes, with kids, friends and possibly a grandparent in tow, hospitality providers and resort destinations are rethinking the notion of family “unit.”

Luxury travel

Luxury travelers over-index heavily in multi-group travel preferences.


But while generations travel together because they want to get closer, that doesn’t mean they don’t need space to stretch out. And the wealthier the traveler, the more space they need.

At Four Seasons Los Cabos at Costa Palmas, 10,000-square-foot villas on the beachfront have been designed specifically for a new generation of wealthy travelers and their entourages. At Four Seasons Resort and Residences Anguilla, stand-alone $6-million villas are attracting European and American families who bring friends and family to stay for extended periods. “One of our recent families decided to purchase a 6,185-square-foot beachfront villa because they have three small children, and the villa affords them the size and privacy to enable the entire family, along with a caregiver and grandparents, to vacation together,” says Nick Cassini, director of sales for Four Seasons Private Residences Anguilla. “They said that this was one of the most important factors in their decision-making.”

At Rosewood Hotels & Resorts, president Radha Arora told Resonance his properties are offering ever-larger suites, villas and residences, from San Miguel de Allende (residences), to Castiglion del Bosco in Tuscany (villas) and Las Ventanas al Paraiso in Cabo (signature villas). The Wall Street Journal reported that Rosewood is increasing the percentage of suites at its resort properties to more than 40% of total rooms, up from around 30%, to accommodate strong demand.

“These multigenerational families that want to travel together take up not just one room, two rooms but a handful of rooms at the same time, driving the occupancy up,” Arora said.

millennial travel Airbnb tourism

The accommodation preferences of Millennials closely track the gilded 1%.


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