Everyone knows Florence. Everyone has heard of Siena and San Gimignano. And these places are, genuinely, magnificent — but in high season they can feel less like living Italian communities and more like open-air museums, dense with tourists and selfie sticks.

Tuscany's true character, however, lives in its villages — the small, sometimes barely signposted medieval burghs that sit atop hills, overlooking cypress-lined valleys, largely unchanged for centuries. These are the places where the Chianina cattle graze on hillsides unmarked by any guidebook, where the local osteria has three tables and a hand-written menu, where you are sometimes the only person in the piazza who doesn't speak Italian.

Here are ten Tuscan villages that deserve a place on your itinerary.

1. Pienza

Designed in the 15th century as the world's first ideal city by Pope Pius II, Pienza is a masterpiece of Renaissance urban planning compressed into a single street. The Pecorino di Pienza cheese produced in the surrounding Val d'Orcia is among Italy's finest. Come for the Piazza Pio II, stay for the view from the cathedral garden over the cypress-studded valley.

2. Montalcino

Home to Brunello di Montalcino, considered by many sommeliers to be Italy's greatest red wine. The medieval fortress at the town's summit offers extraordinary views, and the surrounding Val d'Orcia (a UNESCO World Heritage landscape) is at its most otherworldly in May and October. Book a tasting at Biondi-Santi — the estate that effectively invented Brunello.

3. Pitigliano

Known as Little Jerusalem for its historic Jewish quarter, Pitigliano is one of Tuscany's most dramatic sights: an entire medieval city built atop a volcanic tufa rock outcrop, seemingly growing organically from the cliff. The caves carved into the rock below — the vie cave — were used by the Etruscans and run for kilometres through the surrounding countryside.

4. Sorano

Just 12 kilometres from Pitigliano, Sorano is even less visited and equally spectacular. Another tufa-perched village, with a remarkable 15th-century Orsini fortress and streets so narrow that the buildings overhead nearly touch. Stay at Hotel della Fortezza, built into the ramparts of the fortress itself.

5. Anghiari

Perched above the Tiber Valley near the Umbrian border, Anghiari is where Leonardo da Vinci depicted one of history's great lost paintings (the Battle of Anghiari, now vanished beneath a Vasari fresco in Florence's Palazzo Vecchio). The village is unchanged since the Renaissance; its artisan woodworkers still produce some of Tuscany's finest furniture.

6. Cetona

A near-perfect Etruscan hilltop town, Cetona has managed to attract a discreet community of artists and writers without losing any of its authenticity. The trattoria La Frateria di Padre Eligio — set in a restored 13th-century Franciscan convent — offers some of the most remarkable and soulful cooking in all of Italy.

7. Cortona

Famous to English-speaking readers through Frances Mayes's Under the Tuscan Sun, Cortona — sitting above Lake Trasimeno on the Umbrian border — has somehow resisted becoming a cliché. The Museo Diocesano holds a Fra Angelico Annunciation of staggering beauty, and the evening passeggiata on Via Nazionale remains a genuinely Italian ritual.

8. Barga

In the Garfagnana valley of northern Tuscany, Barga is a medieval gem with a remarkable Romanesque cathedral, a thriving arts scene, and a significant Scottish-Italian cultural connection (many local families emigrated to Scotland in the early 20th century, making it the only Italian village where you might hear Scots dialect in a bar). The surrounding Apuan Alps are extraordinary walking country.

9. Pescia

The flower capital of Tuscany, Pescia sits in the Valdinievole — a lush valley of nurseries and paper mills. Far less visited than the hill towns of the Chianti, it offers a glimpse of working Tuscan life: the fish market on Tuesday and Friday mornings is extraordinary, and the paper museum in the old mill district is a hidden delight.

10. Murlo

With fewer than 800 inhabitants, Murlo is one of Tuscany's smallest villages — and one of its most mysterious. An Etruscan palace was discovered here in the 1960s, and the local museum holds artefacts that have genuinely puzzled historians. The surrounding Crete Senesi landscape — rolling, treeless clay hills unlike anything else in Italy — is best experienced on horseback at dawn.

Planning Your Village Tour

The key to visiting Tuscan villages well is pace — and a car. Rent a small vehicle (the lanes in some villages admit nothing wider than a Fiat Panda) and resist the urge to tick off too many places in a single day.

Base yourself in one of the slower-paced agriturismo estates — many of these working farms offer accommodation that is at once deeply comfortable and completely authentic. Two villages per day is a sensible maximum; often one is better.

"The best of Tuscany is found in the places that don't appear in the tour itineraries — the villages where the bar owner knows everyone by name, and where lunch lasts three hours as a matter of principle."

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If you'd like to design a Tuscany itinerary that goes beyond the obvious — one that takes in the landscapes, wines, and villages that most visitors never find — Extraordinary Travel would love to help. Lura has spent considerable time in these hills and knows exactly where to take you.

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