Secret guide: Tuscany

Tuscany is quintessential Italy, a distilled version of the charms and passions that make the country so unique. Rolling valleys offer up vineyards of international renown, interspersed by a network of startlingly original medieval towns.

Straddling the hills, they sit resplendent in the glowing Tuscan light, inviting any traveller to explore their labyrinthine streets to find hidden enotecas, trattorias, and artisan workshops. Renaissance splendour resides in the region’s famous and largest cities, where Da Vinci, Michelangelo, Dante and Botticelli all leave traces of their artistic prowess. From the famous Piazza dei Miracoli in Pisa to the hidden charms of small towns like Pitigliano, discover Tuscany below with our guide to the must-see and secret gems in this famed region.


This medieval metropolis is a stunning example of age-old Tuscan identity. The terracotta hues blend the labyrinthine streets into an endless adventure of discovery, where enotecas and trattorias are to be found everywhere, offering Tuscan treats. The magnificent, gleaming Duomo is one of the finest in Italy, setting the Gothic mood that befalls the rest of this largely original, medieval city.


Yes, you should definitely visit the impressive Romanesque marvels of the Piazza dei Miracoli. But for a rare chance to explore a city not brimming with tourists (aside from the aforementioned starlet), explore the buzzing piazzas and lively enotecas that this student-town affords.

Barone Ricasoli

No trip to Tuscany is complete without visiting a vineyard for a taster, so why not alight at the oldest in Italy? This grand 11th-century castle towers over the surrounding landscape, a bastion of centuries-old wine-making. It was here that Chianti Classico was born, so kick-back with a glass and enjoy the incredible views over the Tuscan valleys.


Impossibly magnificent, this hilltop village – dubbed Little Jerusalem – rises from the landscape with stark medieval walls signalling its ancient soul. Quiet, non-touristy, this place is packed with isolated medieval splendour. Once home to a large Jewish community (hence the moniker), its museum and specific landmarks only hint at its important history. A true hidden gem.

Fiera Antiquaria

Head to the charming town of Arezzo, for bucket-loads of old-world charms and plenty of antiques. The antique sellers that line the grand medieval piazza collectively display their wares, along with other traders, in the centre of the square once a month. Cherish the date, as the treasures to be found here are outstanding.


Exiled here in 1814, Napoleon would struggle to see the Elba of today. Far from a place of punishment and hardship, Elba is a small island paradise just off the Tuscan coast. With plenty of hikes, biking and kayaking to try out, not to mention epic views and luscious seafood, Elba is an island sanctuary.

Truffles in San Miniato

Another stunning hill-top medieval town (could you ever get bored of them?) renowned for its foodie offerings. Particularly known for the famous white truffle that grows in the outlying forest, head for delectable dining or to hunt for yourself with a cookery class thrown-in. The historic butchers Falaschi is a great spot to pick up cold cuts – most of the restaurants in town buy their meat here.


The Roman amphitheatre in Fiesole is in remarkable condition – so much so, that it’s still in use. The Estate Fiesole summer events are hosted here every year, bringing the ancient and the new together with great artistic flourish. The rest of the town has plenty more to see, plus stunning views over the countryside.

Castello di Sammezzano

A breathtaking technicolor marvel, the castle of Sammezzano is a true hidden gem. Initially a Moorish creation, the interior was decked out in exotic Arabian styles, with an intricacy and eccentricity that clearly saw no bounds. Unfortunately, it has fallen into disrepair, changed ownership frequently, and its future is uncertain; however, very rare public viewings have been known to take place, making for an unmissable and eternally unique experience.

Palio di Siena

High drama and fervent passion frame this centuries-old tradition – a horse race in Siena’s main square between the competing wards of the city. Held twice a year in July and August, the city is alive with shouts, the sound of thundering horses, and an electric atmosphere that is simply unmissable.