Tips on Travel to Tuscany

Get the goods on the logistics of setting up your own family-centric Tuscany adventure

Scenes From Around Tuscany

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We had been talking about this photo op since day one. Our five beautiful subjects sitting on the sprawling green lawn, framed against a backdrop of the stunning Italian countryside. The photo itself sounded easy enough—with so many perfect elements, how could it go wrong—which is probably why we put it off until the end of our week-long stay at a villa in southern Tuscany. But my husband, eight of our closest friends, and I soon learned that trying to get three toddlers and two infants to sit still and smile for a photo is next to impossible. Nevertheless, we were determined. In our minds, we knew it would become the picture that would represent our five-family vacation, the one that we would show our kids one day and ask, "Remember when we all spent a week in Tuscany?"

Of course, they probably won’t remember. At ten months, 11 months, 16 months, two years, and almost three years old, they were too young. In some ways, this was why we planned a family vacation geared toward adults. (News flash: Tuscany isn't exactly known for parades of cartoon characters and kiddie rides.) While we wanted the children to enjoy themselves, we knew this wouldn't qualify as the trip of a lifetime for them (even with their short lives thus far). But that also explains why we organized a group venture; no matter where we went, the kids would have each other.

And so would the adults. It doesn't take a seasoned parent to know that vacationing with children can be tricky. Besides added travel logistics and extra gear, you’ve got to work around sleep schedules and pressures to keep the little ones happy, while also attempting to weave in some grown-up time and a decent dose of rest and relaxation. Traveling as a group would solve some of these issues. With ten pairs of eyes on five children, someone would always be looking out for the tots, allowing us all a little more breathing room. And the camaraderie would provide built-in evening entertainment after the babes' early bedtimes—and, even better, provide a chance to rekindle friendships that had suffered the time-consuming roles of parenthood. On the flip side, whenever we wanted some individual family time, we could take off without leaving anyone by themselves. And as for the kids, they would have a week of consistent playmates.

Nine months out—when we first started to weave this trip together—this approach sounded wonderful. Whether or not our logic would hold up remained to be seen. The long lead time was necessary—there was the villa to book, airplane tickets to acquire, hectic schedules of ten adults to align, and the glorious minutiae of things like international driving permits and debates about which kid (young or old) would be the first to pee in the pool, the latter hashed out by voluminous email exchanges.

Entrusted with finding our vacation digs, my gateway to the wide world of villa options began with a simple Google search. After much scrutiny of what seemed like every villa imaginable, we made our selection—a six-bedroom, two-level, 17th-century manor house in the Val D'Orcia region called Il Casato. From the online description and photos, plus discussions with our rental agent Franco, Il Casato met all our criteria: It had at least five double bedrooms, enough square footage for ten adults and five youngsters to spread out; child-friendly interiors; an outdoor play area for the kids; a pool far enough from the house for child safety; and a location accessible to daytrip destinations. On top of that, the villa owners agreed to provide cribs (at no extra cost) and offered home-cooked meals, for a fee, at our request.