Beyond Florence: Tuscany’s undiscovered towns

Some years ago, I found myself staying in a hotel outside Florence, without having arranged a hire car. With no way to visit Siena or San Gimingano other than spending a gazillion Euros on the hotel’s tour, I decided to walk into the nearest town for a change of scene.  The streets of Tavanelle di Pesa were quiet and unshowy, but I stumbled across a gem of a restaurant, the Borgo Antico, where I ate the freshest carciofi (artichokes) and an unctuous carbonara, while local families tucked into antipasti and tagliata, washed down with carafes of rose. It served as an excellent lesson that Italy’s most popular region is so much more than the big draws – and that smaller, under-the-radar towns are often where you’ll have the most authentic experiences. Here are six such places, all of them oozing classic Tuscan charm.  

Pitigliano

Tucked away in the southerly Maremma region, Pitigliano’s centuries-old houses rise up from a tufa cliff, over 300 metres above sea level. Spectacular from a distance, a lattice of quiet streets wind around the Baroque cathedral, grandiose Orsini Palace and the 16th century aqueduct bridge, with glorious views across the lush river valleys below.

Most famous for its ‘Little Jerusalem’ neighbourhood – inhabited since the 15th century by a vibrant Jewish community – the Synagogue and Museum of Jewish Culture are both well worth a visit. For me though, the greatest pleasure is wandering the narrow streets before stopping for a glass of Bianco di Pitigliano – one of Italy’s best white wines, made in the vineyards that roll out beneath the town.  Lunch choices are plentiful; La Rocca is usually mine – the linguine mancini, rich with olive oil and fresh seafood – is a perfect match for the wine. 

Lucignano

The village of Lucignano has punched above its weight for centuries, due to its strategic location between Siena and Arezzo, but it’s most famous for its unique layout; built as a series of concentric circles. Pop into the Church of San Francesco to see vivid 15th and 16th frescoes and, if it’s open (and the hours it keeps are irregular, to say the least), do visit the Museo Communale inside the Town Hall. Here, the fresco-covered walls of the Sala delle Udienze (Halls of the Audiences) form a spectacular backdrop to the glittering 2.5m ‘Tree of Life’ in the centre. Created by two medieval jewellers, the branches drip with crystals and corals, representing the blood of Christ, with a crucified figure on the top. Afterwards, bag a table on the terrace at La Tavernetta to feast on wild boar ragu and velvety-soft bresaola.  

Cutigliano

Set 700 metres above sea level in the heart of the Apennines and close to Pistoia, Cutigliano has won the ‘Orange Flag’ – awarded to inland villages that have preserved their cultural heritage. The narrow streets, dotted with potted plants by wooden front doors, are shady and cool for a gentle amble; most lead to the central piazza where the saffron-hued Town Hall is covered with coats of arms of the ‘Captains of the Mountains’ over the centuries. Defined by its mountainous location, walking, cycling and hiking trails lead off from the town – a great way to work up an appetite for a late lunch. My pick is Trattoria da Fagaolino, open since the 1950’s, and serving up hearty pastas with a great selection of local wines. 

Monticchiello

Surrounded by the tranquil landscapes of the Val d’Orcia, Monticchiello is smaller than many of the Tuscan villages that draw in the crowds, with a charming central square, Piazzetta della Vittoria, surrounded by quiet alleyways. It’s a great place to come for lunch on a day’s touring (Pienza and Montepulciano are both close by); beforehand, take a stroll along the gravel path that traces the line of the town’s historic walls for some truly beautiful views. La Guardiola, set just outside the walls, has a terrace with more great views; to sit with a ‘Val d’Orcia Mix’ – locally produced salamis, cold meats and pecorino from Pienze – is a glorious way to spend an afternoon. 

Bagno Vignoni, Val d’Orcia

Alongside the bucolic landscapes, the Val d’Orcia is also famous for its hot mineral springs, and Bagno Vignoni differs from most other Tuscan towns by having a central pool, rather than a piazza. It’s not open for bathing, but it’s a lovely place to sit with a coffee and slow the pace for an hour.  If you do want a dip, there are several hotels that offer thermal spas, while the nearby Parco dei Mulini has a shallow outdoor pool that is free to use. For lunch, Il Loggiato is a great choice, with a daily changing menu and a focus on traditional local dishes, including pici al ragu – traditional hand-rolled pasta – and slow-cooked pork. 

Carmignano

Vinophiles will love this charming hill town, dominated by the imposing 10th century fortress and the church of San Michele e Francesco, famous for Visitation – a 16th century panel painting by Pontormo, considered a masterpiece of its kind. The other main draw is the Museum of Wine and Vine, which traces the evolution of winemaking in and around Carmignano, including a proclamation by Grand Duke Cosmo de Medici in 1716, setting out acceptable rules of production. All of which is the perfect precursor to a tasting at Tenuta di Capezzana, one of the region’s oldest vineyards, dating back to the 9th century, or a glass or two with lunch at the Antica Torre.

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