The New Family Vacation

From glamping in Montana to easy mansion living in Jamaica, today’s first-rate family vacation destinations are like your easy, relaxing summers at the Shore, but with way more amenities—and much bluer water. Here, some spots worth exploring together.

Monteverdi in Tuscany makes for a great new family vacation destination.

Rome was full of tourists. Americans, Germans, Australians—I didn’t even get to practice my high-school Italian. It felt like everyone in the Eternal City was speaking English. Which is why our trip didn’t really feel like a vacation until we pulled off the Autostrada and drove through the lone town square of tiny Sarteano, then onto a dirt road that switchbacked through vineyards, olive trees and clouds to the even smaller town of Castiglioncello del Trinoro.

At that point, the directions became vague. “The concierge will be on your left,” they read. But there was no hotel lobby, no glittery sign, no capped b­ellhop—only a path that passed a modest church, a tiny outdoor cafe, and what I could only imagine was an ancient stone wall, dotted with wild red poppies. No concierge. And suddenly, since there was only one road, we were heading out of town. We looped back around, and this time—since, clearly, a car that passes through and doesn’t stop is the equivalent of big news here—the well-dressed staff was standing outside the cafe. They flagged us down, popped prosecco, and said, “Si. Tu sei qui.” We had arrived at Monteverdi.


Everyone dreams of buying a house in Tuscany, but Cincinnati lawyer Michael Cioffi did one better. He bought a series of beautiful but dilapidated buildings in a hilltop Tuscan town with a population that you could count on two hands. Meticulous, historically accurate renovations turned this forgotten village, with views straight out of a travel ad, into a true Italian experience (with only a few fellow foreigners).

The entire town becomes yours while you’re there. The staff is always ready with a glass of perfectly temped local wine, a nibble of local cheese (they’ll point out where in the valley the cows are from), and fresh, delicious, simple, real Italian food. We’ve never had eggplant parm this good. The finer-dining restaurant, the only one in town, is helmed by Chef Paolo. If you reserve one of the villas with a kitchen, Chef Paolo comes to you.

One must-do: finding new places to lounge, like on the grassy terraces that overlook the Val d’Orcia, or near the dipping pool, or on the lower patio with shade from the pergola—you won’t want to leave any medieval stone undiscovered. It’s so peaceful that at night, we sat outside just listening to the silence. Above the building that serves as a small hotel is an actual excavation, financed by the owner. The ruins being unearthed date to the 12th century.

The villas themselves are something out of Architectural Digest. Designed by Rome’s Ilaria Miani, they manage to be both understated and highly styled. A single tawny wooden shelf lines three walls of a room and serves as bench, desk and side table; the antique wooden door is painted bright green; a stainless villa kitchen has reclaimed stools; and a step-down travertine soaking tub is also a shower. The rooms are so harmoniously designed that the flat-screen actually seems out of place.

While your hamlet is hard to leave, this is Italy, and you should explore. Little neighboring towns come with their own histories, eateries and attractions. There are hikes, wineries and natural hot springs. You’re halfway between Rome and Florence and an hour from Siena, which makes this a worthy home base. After you see all the musts—the Colosseum, the Vatican, the Duomo, the Pantheon—with all the other people, all you’ll think about is getting back to your small mountain town.

Monteverdi at a Glance:

Ages: Monteverdi is classy but casual. Babies are welcome; otherwise, it’s best for kids who are mature enough to appreciate the experience.
Kid stuff: There are cooking lessons, a pool, TVs and wi-fi. The staff will help arrange hikes, bikes and horseback riding.
Grown-up stuff: Try winery visits, outlet-mall shopping (hello, Prada), and Fonte Verdi, a day spa built around a natural hot spring.
Together time: Exploring Tuscany’s many small villages.
Eats: The two property eateries are accommodating and delicious.
Quiet time: With some notice, babysitting can easily be arranged.
Getting there: Monteverdi is a two-and-a-half-hour drive from Rome, which has direct flights from PHL.
Stay details: Two-bedroom villas start at 5,500 euros a week (about $7,300). Breakfast (with local yogurt, of course) is included.

Take your family to:

>>A Ranch in Montana: Paws Up
>>A Manse on Mustique: The Mustique Company
>>A Villa in California: Pelican Hill
>>A Cottage in Upstate New York: Mohonk Mountain House
>>A Manor in Jamaica: Moon Dance Cliffs

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