A guide to luxury travel in Tuscany with kids

The best places to visit in Tuscany as a family

With so many villages, towns, and cities to choose from, pinning down precisely the best places to visit in Tuscany with kids can be overwhelming. But that’s where we come in. As luxury travel experts, we’ve weaved our way (families in tow) along everything from the iconic rolling hills of Val d’Orcia (as shown in Gladiator) to the fourteen medieval towers of San Gimignano. Now, it’s your turn.

Florence

The region’s historic capital city (and the birthplace of the Italian Renaissance), Florence is one of the best places to visit in Tuscany with kids. A classic ‘must-do’ destination for history buffs and art lovers, Florence boasts countless iconic sites: the Ponte Vecchio with its tiny ‘gioiellerie’ (jewellery shops), the w-shaped hub of Piazza della Signoria, and the spectacular Duomo (or the Santa Maria del Fiore Cathedral, as it’s also known) . But that’s not all.

Keeping everyone (kids included) happy can be tricky. In Florence, that’s not a problem. Brimming with treasures, it instantly becomes a classroom for curious minds to latch onto as you wander and explore. Whether you’re rolling up your sleeves and mastering that all-important toss in a pizza-making masterclass, cycling through the city’s cobblestone streets, or embarking on a private cruise down the River Arno at sunset, there’s never a dull moment here.

Siena

For a family vacation in Tuscany with a dash of competitive spirit, Siena is the place to be. Twice a year, the city comes to life with the Palio – a nail-biting horserace of immense theatrical proportions. But, in the interim, there’s plenty of things to keep everybody entertained. Whether you’re embarking on a contrade (district) treasure hunt, ticking off the specific flag, animal and fountain that marks each neighborhood, or uncovering the Renaissance masterpieces of the Sienese School of Painting.

The Tuscan countryside

If you’re wondering what to do in Tuscany, don’t worry; we’ve got you covered. A rural paradise filled with cypress trees, wheat fields, and Renaissance settlements, you’ll explore to your heart’s content beneath the Tuscan sun. Cycle along gently rolling hills in Val d’Orcia (the filming location of Gladiator), picnic at family-run fattorie (local farms), or take to the skies in a hot air balloon ride over the sweeping vineyards of Chianti. Here, you’ll embrace the rural way of life.

San Gimignano

With walls dating back to the 13th century, and the city’s historical center boasting UNESCO World Heritage Site accreditation, San Gimignano is one of our favorite places to visit in Tuscany. Take some time to explore the medieval town and 14 of its perfectly preserved towers with one of our expert local guides as they teach you all about this mesmerising city, where families (and competitive neighbors) would once build towers taller than those of their peers as a show of wealth and status.

Our favorite family-friendly things to do in Tuscany

When planning a family vacation in Tuscany, deciding on the places you’d like to visit is important, but so is choosing the activities you’d like to experience there. But with Black Tomato, planning a family vacation in Tuscany is easy, with our Travel Experts on hand to tailor every little detail exactly to you. On our ventures, we’ve traversed the region from end to end with our own families in tow – finding the very best experiences for travelers of all ages. Here’s just a few of our favorites.

Admire the architecture of Florence Cathedral

Kickstart your Tuscany vacation with a private tour of Florence, the region’s mesmerising capital. Accompanied by a private guide, you’ll explore the birthplace of the Italian Renaissance and unravel the city’s history , from its establishment in 59BC to its Renaissance revival in the 15th century and modernisation in the more recent years. Climb the 463 steps of Brunelleschi’s Dome of the Cathedral (or, ‘il Duomo’) for a breathtaking 360-degree panorama. Perched 100 meters above Florence’s terracotta rooftops, you’ll feel as if you’ve stepped back in time to a realm of ambitious Medici, medieval poetry, and the tucked-away workshops of da Vinci where his inventions were brought to life.

Try your hand at Tuscan focaccia-making in Chianti

Today, you’ll head south, driving past Tuscan villas, olive groves and lush vineyards to reach Greve in Chianti. Here, you’ll meet Giulietta, your host and cooking instructor for the day. From the grounds of her hillside Tuscan villa, you’ll embark on a private cooking class, hearing captivating tales of Tuscan cuisine and discovering the secrets of family recipes that have been passed down for generations. Learn to prepare focaccia, the technique of making the perfect risotto con zucca, and the ingredients for Giuletta’s one-of-a-kind lasagne. After showing off your culinary talents, you and your loved ones will enjoy the delicious lunch you’ve prepared, accompanied by a glass (or two) of local Chianti Classico Riserva Badia a Passignano wine – for the adults, of course.

Cycle through the Tuscan hills near San Gimignano

Just a stone’s throw from the medieval town of San Gimignano, you’ll set out on a leisurely⁠ bike ride through the Tuscan vineyards; marvelling at sweeping views of sunflower fields and clusters of Vernaccia grapes (used to create the area’s renowned white wine, Vernaccia di San Gimignano). Like with everything, we’ll tailor it entirely to you. With routes for all ages and abilities, a bike ride is the perfect way to discover the more remote areas of the region. Along the way, stop at a secluded spot for a picnic packed with your favorite snacks and drinks.

Cooking classes

Another of the best things to do in Tuscany with kids is to take part in a hands-on cooking class. Italy is renowned for its mouthwatering cuisine such as fettucine alfredo and fresh tomato bruschetta and traditional recipes passed down from generation to generation. And Tuscany is no different. Rolling up your sleeves, together you’ll learn the secrets of crafting the perfect pizza, pasta, or gelato. Just say the word and we’ll make it happen.

Where to stay in Tuscany with kids

Deciding where to stay in Tuscany with kids can be a little daunting. After all, there’s a lot of choice. But not to worry. After countless trips to this captivating region, we know the best child-friendly hotels around. Below, our favorites.

COMO Castello del Nero

High in the Tuscan vineyards and twisting olive groves of Tavarnelle Val di Pesa, you and your family will stay in a beautifully renovated 12th-century castle: COMO Castello del Nero. With rooms featuring traditional castle touches like vaulted ceilings, mosaics, and ‘cotto’ floors, you’ll feel as if you’ve wandered through the pages of your favorite fairytale. Here, there’s also a dazzling array of activities to keep the kids (and yourselves) entertained. Whether that’s enjoying a picnic among the vineyards, embarking on a truffle hunt, riding on horseback through the surrounding hillsides, or soaring over the valley via hot air balloon. At this 740-acre estate, anything is possible.

From a sustainability perspective, the hotel also has a strong focus on farm-to-table experiences. You can even choose your own produce directly from the kitchen garden to be prepared into your meal.

Hotel Lungarno

Located at the heart of Florence, Hotel Lungarno is perfectly positioned so that you can explore Tuscany’s capital city every hour of the day. Perched over the Arno River, and just steps away from the Ponte Vecchio, the wonders of Florence are quite literally on your doorstep. Just thirty minutes from both the airport and the Tuscan countryside, you’ll be strolling those cobbled streets with a gelato in no time. No more ‘are we there yets’.

For the art enthusiasts in your family, this is the place to be. The hotel’s walls are adorned with masterpieces from the likes of Picasso and Cocteau and the Uffizi Gallery is just a five-minute walk away.

Borgo Pignano

If you’re seeking an idyllic place to stay and an exciting variety of things to do in Tuscany with kids, Borgo Pignano is for you. Set amongst 750 hectares of rolling Tuscan hills and 30-minute drive from San Gimignano, this unique retreat was originally a hamlet dating back from the Etruscan times. For families or those traveling with friends, find your own space as you hole up in one of the hotel’s spacious villas and cottages.

Now, for the activities. For kids, there’s plenty to keep them entertained while encouraging them to connect with the spectacular natural surroundings. They can take a tour of the verdant vegetable garden, learn to make fresh pasta and soda bread, craft homemade soaps and honey with the beekeepers, check out the hotel’s solar energy efforts, or enjoy a yoga class in the studio. Borgo Pignano also boasts a heated infinity pool overlooking the Tuscan hills, a spa, and open-air pizza evenings.

Relais Borgo Santo Pietro

A beautifully restored 13th-century country villa set amongst a 200-acre estate, Relais Borgo Santo Pietro is one of our favorite places to stay in Tuscany with kids. Each elegant room feels as if you’ve stepped back in time – think glittering chandeliers, hand-painted murals, and tapestries draped along the walls. But for kids, there’s all the mod-cons too, including discreetly concealed plasma TVs and tucked-away iPads.

You and your family will spend your days strolling through the fragrant rose gardens, exploring the nearby medieval villages of Palazzetto and Chuisdino, swimming and splashing to your heart’s content in the striking infinity pool, and going for picnics in the tranquil countryside.

Best time to visit Tuscany

To really get the most out of your family vacation to Tuscany, the best time to visit Tuscany is April through to November. However, our favorite months for a family Tuscany vacation is June, when the hills are scattered with wildflowers and the weather is warm, or October when truffle hunting season is in full swing and the Autumn leaves are glowing.

Why book a trip to Tuscany with Black Tomato

Our family trips to Tuscany (and everywhere else) are created by families, for families. Many of us are parents ourselves, so we know first-hand the challenges, time and energy that goes into planning a successful trip. We’re here to make that all fade away, to make everything flow seamlessly. So that you can focus on what’s really important: spending time with your loved ones and creating unforgettable memories together. Whether that’s flying over sun-soaked Tuscan vineyards by hot air balloon, learning how to make the perfect Italian pizza with that all-important signature toss in Florence, or getting swept up in the cheers and the chaos of Siena’s nail-biting Palio.

We understand that every family is different, so – naturally – every family trip to Tuscany should be different too. We’ll learn what precisely makes your family tick, listening to each member of your clan’s ideas, passions, favorites (snacks, games, you name it) and ‘must-dos’. Whatever you’re dreaming of, we’ll make it happen.