Sure, the House Has High Chairs. But What About a Roman Gladiator?

A few summers ago, Rebecca Messina watched her children Zara and Luca, then 6 and 4, squish tomatoes at Casa Carcicera, a picturesque villa in Southeastern Sicily. The vacation scene bordered on cinematic: Their tiny hands maneuvered thin slices of eggplant as a local cooking instructor — with the last name Amore — supervised encouragingly.

“We’ve always believed that your kids should fit into your life, so we had to make the trip something they’d look forward to,” said Ms. Messina, 46, a San Francisco-based tech executive. “Sicily is famous for its cooking, and we wanted to include them in that experience. We don’t just want them only plopping in front of the pool or the TV.”

For Ms. Messina and other parents with the wherewithal to travel internationally with children, villas are as practical as they are romantic, with many bedrooms under a single roof, ample communal space, a kitchen, and often a private pool and yard.

Yet achieving a family-friendly version of the “Under the Tuscan Sun” idyll goes beyond having high chairs or play areas. To meet increasing demand, luxury villa companies and travel advisers are stepping in to design culturally immersive activities — all for guests who can count their age on one or two hands.

“People used to be very happy to get a babysitter. Now we’re hearing, ‘If we did this or that cultural experience, could we do a junior version so the kids can participate as well?’ said Philip Leighton, the villa program manager at Abercrombie & Kent Villas, which has a portfolio of about 600 private homes around Europe.

Abercrombie & Kent has delighted children staying at Il Palagio, a 15-bedroom Tuscan villa (from $76,032 a week), with visits from a professional falconer, and once organized a perfume-making workshop for a 4- and 6-year-old staying at La Corniche (from $10,427 a week) on the French Riviera.

Although certain top-tier hotels might also be able to coordinate such pursuits, the cost of booking multiple rooms — say, in the case of a multigenerational group — quickly adds up. A 2018 Skift survey of more than 1,300 affluent travelers found that 64 percent of those with children prefer vacation rentals to hotels.

One luxury villa company that caters to families is The Thinking Traveller, which manages Casa Carcicera (from $3,696 a week) and about 220 other privately owned villas around Europe. In Sicily alone, youngsters can watch a private puppet show ($1,679) at Don Venerando (which starts at $6,768 a week), learn to make marzipan fruit ($56 per person) at I Lentischi (from $3,979 a week), take watercolor-painting lessons ($145) at Il Palmento dei Castagni (from $4,532 a week), and go olive-picking (gratis) at Domus Olivae (from $13,407 a week).

“For children, villas are educational — they can see how people in other countries live. And for parents, life in a villa is stress-free. After a busy year, staying together as a family is a very relaxed experience,” said Rossella Beaugié, who co-founded The Thinking Traveller with her husband, Huw.

To bring The Thinking Traveller’s kiddie offerings to life for guests, the Beaugiés test-drive the company’s villas and vendors — cooking instructors, tour guides — with their children (ages 15, 13, 11).

“Our daughter still remembers the first time she took her bucket of handpicked olives to the press, saw the squeezing process and walked away with olive oil,” recalled Ms. Beaugié.

David Prior, the co-founder of PRIOR, a members-only travel company which plans worldwide journeys and events, has also used his family as guinea pigs. Last year, on an 18-day Japan trip, his crew of 13 — ranging from 8 months to nearly 80 years old — piled into two connecting machiya houses, essentially urban villas, in Kyoto, where the children tried everything from samurai knife-making and kimono-tying to taiko drumming.

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“When we’re designing experiences for kids, it’s like a Pixar film: It needs to be colorful and stimulating, and it needs to grab their attention,” said Mr. Prior, whose team at PRIOR last summer arranged a craft room and a plein-air watercolor class, complete with child-size easels, for four families renting a 17th-century villa in Siena, Italy. “People want to spend quality, concentrated time with their families, learn new skills and enrich their lives.”

According to a 2018 report published by the Family Travel Association and New York University that surveyed more than 1,700 parents, the two chief motivations for traveling as a family are the opportunity for children to see new places and gain new experiences, and the chance to bond.

“These trips are about disconnecting to reconnect and building lifelong memories. With so much social media, parents are trying to regain the meaning in travel,” said Jack Ezon, founder and managing partner at Embark, a travel company focusing on luxury multigenerational and family trips.

Last year, for a family of 11 renting Villa Nocetta (from $5,470 a night), a six-bedroom villa in Rome, Embark (then part of Ovation Travel Group) worked with a local destination-management company to rent out the Circus Maximus and hired actors to lead educational gladiator games for the six children, ages 10 to 15. That vacation also included a gelato-making lesson in a fifth-generation gelateria and a citywide horse-and-chariot scavenger hunt.

And then there’s what Mr. Ezon calls the “best-case scenario”: rentable stand-alone villas at luxury hotels.

Children at Su Casa (from $10,000 a night), a five-bedroom villa at Dorado Beach, a Ritz-Carlton Reserve, in Puerto Rico, can bake cookies in a solar oven or participate in ecology-themed scavenger hunts. At The Muraka (from $40,000 a night), a villa at Conrad Maldives Rangali Island, little ones can “glamp” in an undersea suite while marine experts — also trained babysitters — read them bedtime stories.

“Another beach vacation is not going to move the needle. You want to create a legacy; you want to create something for your family name and heritage to grow from,” said Mr. Ezon.

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