With their winding medieval streets, ancient architecture and unrivalled landscape, the hilltop towns of Tuscany have remained largely unchanged for hundreds of years. Tucked into the verdant hills, these towns lie amidst vineyards and olive groves, where local grapes are transformed into robust “Super Tuscan” wines, and aromatic sun-dried tomatoes and olive oil are enjoyed alongside rustic homemade pasta and crusty bread. A region that fully embraces its inherent beauty and unhurried pace of life, Tuscany’s hilltop towns are the perfect place to experience authentic Italian culture first-hand.


Hilltop Towns of Tuscany

Try the therapeutic water of Montecatini © iStock / Frankvanden Bergh

In the sun-soaked hills between Pisa and Florence lies the medieval spa town of Montecatini, clustered around Tuscany’s natural thermal springs. Named a ‘city of the arts’, it’s no surprise that artists and designers – from René Magritte to Versace – have found inspiration here, with many of these works now on display at Montecatini Terme Contemporary Art. Set amid rolling hills and towering cypress trees, the town’s 18th century Belle Epoque and Art Nouveau buildings overlook a spectacular natural canvas that could tempt even the most timid of painters to pick up a brush.

But it’s the natural flow of spring water that really makes Montecatini remarkable. Famous the world over for its ancient baths, Montecatini has attracted all manner of visitors with the promise of its therapeutic thermal treatments; movie stars such as Clark Gable and Katharine Hepburn are even rumoured to have taken the waters here. The 14th century Tettuccio Terme is the main draw, where tall marble columns encircle an open-air atrium, housing these health-giving pools.

Just outside this historic city, the Callistri family have owned Borgo della Limonaia farmhouse since 1700. Here, amidst the olive groves and lemon trees, the family produce fruity red wine and fragrant olive oil, while welcoming Trafalgar guests into their home to share stories and dine on home-made Italian fare made from local, organic produce.


Hilltop Towns of Tuscany

The world’s most exciting horserace, Palio di Siena © iStock / mrohana

The UNESCO World Heritage city of Siena draws travellers from far and wide for its ornate architecture and exquisite artworks, as well as The Palio di Siena, the city’s dramatic and fiercely contested horse races. Dating back to the 12th century, these thrilling spectacles still take place twice a year in the fan-shaped Piazza del Campo, the historic heart of Siena.

At the centre of the piazza sits the city’s Gothic palace, the Palazzo Pubblico, and its 14th century clock tower. From the top of the tower’s 400 stone steps, panoramic views unfold over the city, which finally gives way to the rich colours of the Tuscan countryside. Perhaps Siena’s greatest architectural feat, though, is its cavernous marble cathedral – widely regarded as Italy’s most impressive. From Giovanni Pisano, who created the colourful marble façade, to frescoes by Pinturicchio and sculptures by Michelangelo and Gian Lorenzo Bernini, this is a place where the majesty and emotion of Italy’s cultural heritage comes to light.

Fattoria di Petroio winery and estate lies in the Chianti hills just outside the city, and as a historic marker between Siena and Florence, is home to ruins that span many centuries. The Pallini-Lenzi family, who have run the estate since the 19th century, now produce classic Chianti wines here. Welcoming guests into their home and inspiring visitors with tales of Tuscan winemaking and the estate’s fascinating past, the family cooks up tantalising Italian dishes like Grouper fillet with zucchini flowers, which is washed down with the estate’s own wine.

San Gimignano

Hilltop Towns of Tuscany

San Gimignano overlooks Tuscany’s beautiful vineyards © iStock / bluejayphoto

With its ring of medieval towers, the small, walled town of San Gimignano can be seen from afar, set into the hillside overlooking the surrounding valley and vineyards. Of the 72 towers that once rose above the town, 14 still remain, making it a treasured UNESCO World Heritage site with a skyline that’s given it the name ‘medieval Manhattan’.

Housed within these historic buildings is an astounding collection of 14th and 15th century paintings, alongside magnificent frescoes and friezes. On the town’s atmospheric streets, pilgrims once trod on their long and arduous journey to Rome, while outside the town walls, vineyards flourished with the region’s indigenous Vernaccia grapes, known today for producing some of the best white wine in Italy.

Aside from Tuscany’s affluence of wine, olive oil and saffron, San Gimignano is also famous for a sweeter sort of delicacy, the deliciously crumbly pine nut cake, Pinolata, not to mention some wonderfully indulgent gelato. Famous for inventive flavours such as saffron and pine nut, Gelateria Dondoli has won culinary awards worldwide.

Hilltop Towns of Tuscany

Relaxing with a glass of wine at a Tuscan vineyard © Trafalgar

Visit these hilltop towns on the Rome and Tuscan Highlights tour with Trafalgar

Header image: Explore the Tuscan vineyards © iStock / franckreporter 

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