A Toddler-Friendly Tuscan Holiday with Ciao Bambino

When Emma Crosby and Jeremy Peters decided on a trip to Tuscany with their toddler daughter, Mary, they reached out to our Ciao Bambino planning team for help. Needless to say, we were up for the challenge! Our Italy expertise runs deep — we’ve been working with families of all ages to plan unforgettable vacations here since 2004. Read on for Emma’s rave review of our service!

Travelling around Tuscany with a toddler! Were we, as Italians say, a little pazzo in the head? And could we still have an out-of-this-world experience, even though it’s now more about Aptamil than Aperol at aperitivo time?

Ciao Bambino was our starting point, and what a lifeline they provided! The CB team seemed to know Tuscany like the back of their hand and, crucially, they had a very clear idea of what would and wouldn’t work with 10-month-old Mary in tow. Within a few days we had our itinerary sorted. Rural life, check. Wine tasting, check. Beach time, check. Cultural experience, check. Spa time? Oh yes, check. Armed with Ciao Bambino’s encouraging advice that Italians love children, we landed at Pisa airport and arrived 2 hours’ drive later in the Val d’Orcia, where rolling hills, rustic farmhouses and rural life abound.

Tuscany with a Toddler

Val d’Orcia

La Bandita was our first pit stop. It’s a 200-year-old property with an incredible hilltop setting, converted into a cool minimalist villa by a former U.S. music executive. Its home-from-home attitude worked great for us. The property has lots of space to spread out as well as an outdoor pool, and we could use the villa’s kitchen for Mary anytime. Not that I lifted one utensil, mind, as the chef rustled up delicious dinners with fresh ingredients bought daily.

Baby food is a bit of an anathema to most Italians; here everybody eats together at mealtimes and children enjoy the same menu as the grownups. Not sure how this would work out, I was pleasantly surprised to see how much Mary relished tackling her plates of fresh pasta. And despite most of it ending up on the floor, it didn’t seem to faze anyone. Guests eat round a communal table at La Bandita, which we really enjoyed, but that might not suit all, especially if you want some privacy.

There’s plenty to do in the surrounding area for kids of all ages. The perched hilltop town of Pienza is a great spot for people-watching over a cappuccino. And it would have been rude not to taste the local tipple, the Brunello di Montalcino, which just happens to be one of Italy’s finest red wines. With plenty of vineyards in the vicinity, Mary — very helpfully for us — took our wine tasting in her stride.

Forte dei Marmi

Most Brits and Americans bypass the beaches in Tuscany, but I wanted to dip Mary’s toes in the Mediterranean for the first time, so after a few nights in our rural idyll, we bundled back into the car and headed west to Forte dei Marmi. With the Apuan Alps framing miles of wide, sandy beaches, Forte dei Marmi is a stunning spot. The resort has a down-to-earth Hamptons-like charm; the expensive clothes shops are the only giveaway that this is a holiday destination of the wealthy.

Italians somehow manage to make even sunbathing stylish, and here beach clubs rule. There’s row after row of brightly painted, immaculately kept sun loungers, with matching umbrellas and chairs. In fact, the facilities are perfect for families; there are restaurants, cute changing huts, plenty of space for running around and plenty of shade too. Each club has its own life guard, a big thumbs up for those with little ones. Another plus for families is that everyone cycles in Forte dei Marmi. With bicycle lanes and rental shops galore, even a toddler can be safely strapped in and carted around. After a few days of being cooped up in the car battling Val d’Orcia’s winding roads, it was bliss to dump the keys and get on two wheels.

Not wanting to venture too far from the beach, we stayed right opposite the seafront at Hotel Byron. It’s a fantastic family-run hotel with the old-school glamour that Italians do so well. We stayed in one of the hotel’s ground floor suites, which was great for stroller access and had lots of crawling space for Mary. Another plus is the hotel’s Michelin-starred restaurant, Magnolia — upscale but not uptight. Call it cheating, but we procured the services of the hotel’s nanny for a few hours at a very good rate. Mary had a wonderful time being entertained by someone new and far more interesting, and Mum and Dad feasted on gamberi and risotto. Everyone’s a winner!

Florence

So far so good, but how about throwing in a cultural pit stop in Florence with a little one? Ha, we thought — now the wheels will come off! Surprisingly enough, they didn’t, and again the hotel made all the difference. We stayed at the Four Seasons Firenze. Yes, it’s an expensive treat. But the wonderful location, in Florence’s biggest private park with a fabulous heated outdoor pool, was worth it. The hotel is within spitting distance of the Duomo and the Accademia; we ventured out to give Mary her first taste of sightseeing and made a hasty retreat to our urban oasis when the crowds became too much.

Although the Four Seasons is beautiful (it’s a renovated palace that belonged to one of the Renaissance’s most powerful families), it couldn’t have been more child-friendly, despite our worries that our little adventurer would go barreling into some Murano masterpiece. The concierge organises a host of fun kids’ activities — who wouldn’t want to go on a gelato tour of Florence? Cooking classes are a favourite, and so too are art lessons if you have a mini Michelangelo in the family.

Our bedroom was kitted out with everything a baby could need: fresh fruit, a bath seat, a nappy bin, baby toiletries, even a mini crockery set, bathrobe and slippers. And Mary delighted at the attention she received at mealtimes. With her own menu choices and the cooing staff, she was one spoilt bambino! It wasn’t all toddler time, though — wanting to enjoy one romantic evening in Florence, we hired a babysitter and enjoyed a delicious al fresco dinner at the hotel’s Michelin-starred restaurant, Il Palagio. Bellissimo!

Casole d’Elsa

To finish off our trip, we headed back into the heart of the Tuscan countryside, near to the town of Casole d’Elsa and within easy reach of Siena and San Gimignano. The scenery here is the stuff of postcards, jaw-dropping gorgeous. Even Mary stopped chewing on her breadstick to admire the sunsets. We stayed at Castello di Casole, a medieval village that’s been remodeled into a 41-room boutique hotel, with three onsite restaurants and a fabulous spa.

Again, this is a great place for families. With acres and acres of estate land to explore, there are tonnes of outdoor activities: horseback riding, hiking and mountain biking, to name but a few. The restaurants cater for all tastes; a great trattoria, with its own wood-fired pizza oven, is a real hit with the kids and a fine dining experience for the adults when it’s time to call in the babysitters. All rooms have been purposefully made into suites, with luxurious bathrooms as big as the bedrooms.

We arrived at Castello di Casole after a week on the move, and despite our best intentions to see the local gems, we tore up the sightseeing schedule and decided this was the place to flop. We picked our spot by the infinity pool (heated, so Mary could happily splash around in the shallow end), and ordered chilled glasses of Pinot Grigio to toast the view. Molto bene!

Relevant Links:

Browse all family-friendly accommodations and things to do in Tuscany on Ciao Bambino

How to Make Traveling With Toddlers Fun (Yes, Fun!)

Essential tips for a farm stay in Tuscany with kids

Tips for exploring southern Tuscany with kids

Best Tuscan hill towns with kids: I heart Pienza

Things to do in Siena with kids

Four Seasons Hotel Firenze: A resort oasis in Florence

Editor’s Note: Photos by Jeremy Peters.