Bringing kids to Tuscany, the most romantic of Italian regions, seems almost as absurd as letting your five-year-old order a $50 truffle-garnished hamburger. Will your brood be able to appreciate fully the vineyard dotted vistas, quaint piazzas, and history lessons around every corner? Not very likely. But there is plenty in Tuscany to appeal to the bambini.
The obvious starting point for a Tuscan vacation is Florence, where the surfeit of art — and other travellers — is mind-boggling. Pisa, too, with its iconic Leaning Tower and proximity to Aeroporto Galileo Galilei, Tuscany’s largest airport, is an inevitable stop. But the real challenge lies in deciding where to go after everyone has had enough of shuffling past nude Michelangelos and brushing shoulders with tour groups.
Our top five suggestions include a mix of cities and villages, five-star resorts and country homes. You can plan a whole vacation around any of these sites. Or, if your family is lucky enough to have a long stretch of time, you can create an itinerary that includes all of these locales. Believe it or not, a Tuscan trip with the kids can be as good as — or better — than the one you dreamed of before you started a family.

Lucca
Travel literature likes to talk up Tuscany’s hill towns, but little Lucca, which lies in the valley of the Apuan Alps, lives up to the hype. A compact city center of a few manageable sites, Lucca’s most family-friendly feature is that it is almost entirely closed off to cars. Bicycles — albeit older, single-speed types — rule the roads here, and an umbrella stroller wouldn’t be out of place, either.
Head to the tourist kiosk in Piazzale Verdi, where, at €2.50 per bike per hour, you can rent bikes for the entire family — bicycles equipped with baby seats are also available at no extra charge. With your transportation set, pedal from one piazza to the next. Or, take a spin on top of Le Mura, the city’s medieval fortifications that do double-duty as Lucca’s public parks and passegiata paths.
Staying overnight, when the city has been drained of its tour bus crowds, is the best way to do Lucca with kids. Hotel Ilaria, located along a canal near the Botanical Gardens, has wi-fi, satellite tv, and babysitting services, as well as free bikes to use during your stay.
Hotel Ilaria, suites from €180
Tuscany: Runners-Up
Arezzo

The genius of Il Borro, a 2,000-acre country estate just a few miles from Arezzo, is that you can physically contain your kids without containing their enthusiasm. Owned by the famous Ferragamos, who redeveloped this vast Arno Valley lot to use as a family retreat, Il Borro includes farm land, complete with orchards, olive groves, sunflower fields, and vineyards; wilderness areas for mountain biking, horseback riding, and fishing; and an entire medieval village of shops, rentable apartments, and holiday homes.
While you’re sipping the latest vintage from the Borro’s cantina, your kids can play in the swimming pool or on the full-size soccer pitch. Resident artisans provide a full roster of courses, such as ceramic making, wood-turning, painting, and cooking, so your family has plenty of opportunities to spend some quality time together. But, should you wish to venture out to Arezzo’s antique market or to the Prada outlet in Montevarchi senza bambini , you can call in one of Il Borro’s team of babysitters.
Il Borro — 3 bedroom apartments start at €350
Siena

The Palio horserace, a twice-yearly event on July 2 and August 16, is Siena’s biggest — and, arguably, most kid-thrilling — attraction, pitting a selection of Siena’s seventeen districts against one another in a breakneck derby around the main Piazza del Campo. But, unless you’ve got a masochistic need to herd your group through throngs of worked-up race fans, you’ll visit at any other time, when the shell-shaped piazza is a stage for flocks of pigeons, and, yes, handfuls of day-trippers.
Kids who are into Eragon but haven’t quite moved on to D&D will dig Siena for its moody, medieval feel, while the young ones will be able to make a game looking for the mascot of each neighborhood. Each district, or contrada, is represented by an animal, such as a tortoise or owl, or by something more nebulous, like a forest, which makes a simple family stroll through Siena’s cobbled streets more like a scavenger hunt.
Although the city has several worthy hotels within its borders, a holiday here is best when coupled with a stay in the Sienese countryside. Hotel Borgo Grondaie, located about a mile outside of town, offers comfortable apartments with kitchenettes and washing machines.
Hotel Borgo Grondaie, Apartment for four people start at €178
Collodi

It isn’t exactly Disney World — or EuroDisney, for that matter — but the Parco di Pinocchio is the spot in Tuscany to bring your grade schoolers, if only so they can commune with other kids their age. Pinocchio Park gets its inspiration from the world’s best selling children’s book, written by Collodi son Carlo Lorenzini. The original story about the mischievous puppet is a much darker tale than Walt would have us remember.
If you think your kids can handle encounters with grotesque, bronze sculptures, intimidating topiary, and original Pinocchio characters, such as the coffin-carrying rabbits and the great whale, then you’ve just bought yourself a few hours without the kids bouncing off the walls.
Located about halfway between Lucca and Florence, Collodi is ripe for a daytrip. But if you want to keep it local, head south to the spa town of Montecatini Terme. Hotel Columbia has discounts and amenities for kids and relaxation treatments for mum and dad.
Parco di Pinocchio:
http://www.pinocchio.it/old/uk/infouk.htm
Hotel Columbia, suites from €150 (or $205) per night
Forte dei Marmi

When all else fails, you can always pack ‘em up and head to the beach. Forte dei Marmi isn’t just any beach, though. This seaside town on the sandy Riviera Versilia is like the Tuscan Hamptons, with a walkable downtown, fine dining, and prime people-watching.
Within sight of the colorful umbrella-dotted beach, Hotel Il Negresco is a godsend for parents who want to soak up the sun without having to worry too much about the kids. The hotel provides children with drawing kits, bike rentals, nighttime cartoons, and kid-sized portions at dinner. A swimming pool and a supervised play area also keep them busy. Adults are treated well, too, with amenities like an outdoor Jacuzzi and discounts at the local golf club. You can even have the concierge call in a local nanny — for an extra €25 per hour. This place is like the Hamptons, after all.
Hotel Il Negresco, sea view rooms start at €290






Great guide, some really versatile options.
For anyone staying in Siena, I know the Acqua Village water park in Follonica is popular with kids, especially to break up a week of sightseeing in the hot sun. It’s not the most historical experience, but you know what kids are like!
I actually helped produce a guide for Tuscany with kids, which could be useful as well: http://www.to-tuscany.com/local-tuscany/tuscany-for-children/
Annelies
Nice guide, but don’t forget San Gimignano, a small medieval village near Siena, it’s a total charm!
Mari