Set amongst rolling green hills, cities of art and a sun-drenched coastline, Tuscany offers the perfect setting for a family holiday in a villa in Italy. This region combines cultural heritage, unspoilt nature and the Tuscan way of life, with activities suitable for all ages. From the medieval streets and museums of Florence to the Forte dei Marmi beaches and the hilltop villages of Val d'Orcia, Tuscany has everything you need for a perfect family holiday.
Finding the best place to stay in Tuscany depends on your travel style, whether you prefer the peaceful countryside, historic towns or coastal settings.
The beautiful city of Florence unfolds like an open-air museum, where every square and every alleyway tells the story of the Renaissance. The Duomo of Santa Maria del Fiore dominates the historic centre and captivates adults and children alike with its majestic proportions. Nearby, the iconic Ponte Vecchio, a medieval bridge lined with goldsmiths’ shops, offers a stroll across the Arno River with views of the surrounding hills. Above Florence, kids can pretend to put on plays in the Roman Amphitheatre in Fiesole. Between visits, gelato breaks in shaded streets in the centre of Florence provide a pleasant interlude to the day and allow you to recharge your batteries to continue exploring this cradle of the Renaissance before returning to the comfort of your villa in Tuscany.
The Leaning Tower of Pisa immediately fills children with wonder as soon as they arrive in Piazza dei Miracoli. The square’s vast lawns are perfect for relaxing after the visit to the city's main attraction, and provide a natural playground where everyone can rest at their own pace. A stroll along the Arno River lets you explore the city further, amidst colourful façades and bridges spanning the river in a peaceful atmosphere.
Siena reveals its medieval heritage with undiminished elegance. Piazza del Campo, home of the famous Il Palio horse race in the summer months, is the beating heart of the city and remains one of the most beautiful places in Italy. The pedestrianised narrow streets leading down to the square are easy to explore with children. People can feel the medieval atmosphere on every street corner, amongst ancient towers and terracotta façades. The city’s medieval heritage can be explored effortlessly in this city on a human scale where history remains alive and accessible.
Between cultural stops, the Tuscan coastline offers a relaxing break for the whole family. In Forte dei Marmi, the gorgeous beaches are well-maintained, perfect for families to unwind. Further south, the Maremma coast reveals a wilder side, with unspoilt natural landscapes and dunes fringed by pine forests. Make the most of the seaside to alternate between swimming, coastal walks and exploring the seabed whilst diving or snorkelling. In Maremma Nature Park, accessible trails allow you to observe migratory birds and explore the marshes on foot or by bike.
South of Siena, Val d'Orcia offers one of Tuscany's most iconic landscapes. Family-friendly walks and hikes allow you to explore this beloved area, where every hilltop offers a view of the valley. It is in this unspoilt countryside that the essence of rural Tuscany is revealed, amidst olive groves, traditional farmhouses and ochre-coloured dirt tracks - the ideal place to slow down and soak up the natural beauty of this region.
Chianti offers a different take on the Tuscan countryside that is more forested and undulating. Walks through vineyards and oak forests appeal to families seeking an authentic experience. The idyllic atmosphere of this wine-growing region delights visitors' taste buds, as they watch olive oil and local cheese being made and sample Italian specialities on the farms. The sunset over the Chianti hills is a truly special moment, when the low-angled light carves out the contours of the Tuscan mountains.
Tuscany is home to charming villages where architecture, landscapes and la dolce vita harmoniously blend. Montepulciano, perched majestically on a hilltop, showcases its Renaissance treasures, whilst Pienza, the papal town of the Val d'Orcia that is a UNESCO World Heritage Site, invites you to stroll amongst its gourmet shops. For a more peaceful stopover, the small town of San Quirico d’Orcia charms with its Italian-style gardens.
Must-see, San Gimignano is recognisable by the silhouettes of its medieval tower houses surrounding the Piazza della Cisterna, Collegiata di Santa Maria Assunta and Piazza del Duomo. Finally, Lucca offers a unique experience. People enjoy exploring its ramparts by bike, providing a ride with views of the medieval town’s bell towers for a true journey back in time.
Villa Farfalla in Lucca is the perfect spot for families, with its private grounds, heated swimming pool and tennis court, just a stone’s throw from the town’s famous ramparts.
Perched above Pistoia, Villa Massa offers an elegant retreat amidst olive groves and a panoramic swimming pool – the ideal haven for savouring la dolce vita near the beautiful city of Florence.
Casale Catalina in Siena combines the character of a historic home with the luxury of modern design, featuring an infinity pool with panoramic views of the hills.
Overlooking the Val d'Orcia, Villa Monti offers a haven of absolute tranquillity, with its spectacular views of the iconic cypress trees and the ochre-coloured dirt tracks.v
Set amongst Florence, Siena, Val d'Orcia, Chianti, Arezzo and Lucca, Villanovo offers a selection of hand-picked villas, designed to accommodate families seeking space and comfort. Our villas provide the perfect base for exploring the best places in the region: the vast majority feature a private swimming pool nestled within gardens overlooking the Tuscan hills, whilst others offer authentic charm and are situated close to local villages. These villas provide a natural setting for family holidays with children, where everyone can set their own pace between swimming, al fresco dining and excursions to discover Tuscany and Italy.
From the moment you book, Villanovo’s destination specialists help you choose the right villa based on your preferences, family size and the time of year. Before your arrival, the dedicated concierge service takes care of the initial arrangements: grocery deliveries, a private chef, bike or car hire, and bookings for restaurants, wine-tastings, or guided tours of museums. During your stay, the teams remain available by phone, WhatsApp or email to recommend their top picks for local places or book activities like hiring a truffle hunter for Tuscany's precious tubers.
