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Montepulciano

Montepulciano is effortlessly civilised and makes a beguiling base should you have accommodation nearby. Its appeal lies in the mellow mix of Renaissance palaces and moody wine bars made for sipping Vino Nobile di Montepulciano. Like all quintessential Tuscan towns, it is built on a human scale so designed for strolling and relaxing on a Renaissance stage set, with set-pieces around every corner.

The main square sits at the town’s highest point, both culturally and geographically.

On one side is the 15th-century Palazzo Comunale (Town Hall), a miniature version of the Palazzo Vecchio in Florence.

Pienza

Pienza is an exquisite Renaissance doll’s house, almost too perfect for its own good. Pienza’s popularity has been boosted by its Unesco recognition and by its attraction as a film set. More heretically, visitors flock to the town almost as much for its superb array of Pecorino cheeses as for its perfect Renaissance architecture.

Before looking at specific buildings, just soak up the atmosphere. Pienza is a Utopian town. After Pienza, other cities in Tuscany or elsewhere are liable to look chaotic.

The scenery around Pienza is equally lovely, with the town framed by chestnuts and cypresses, olive groves, poppies and sunflower fields.

Bath Vignoni

Bagno Vignoni, a beautiful village in the Val d’Orcia, a hamlet of San Quirico d’Orcia, is famous for its unique square, which has a large pool fed by a hot thermal water spring in the center. But it is also famous for its free hot springs, the Parco dei Mulini, where the thermal water has carved several pools in the rock where you can bathe.

The waters gush out from several springs at 50°C but, due to the fact that they flow through natural channels for long stretches under the open sky, the perceived temperature is significantly lower (as a result, Bagno Vignoni is preferred by spa-goers especially in summer), and are indicated for the treatment of rheumatic and respiratory ailments.

Arezzo

When visiting Tuscany, the city of Arezzo, nestled in the heart of the region, invites visitors to explore its rich history, culture and artistic heritage, making it worth a visit. Renowned as the birthplace of famed artists like Piero della Francesca, this enchanting city boasts captivating medieval architecture, including the iconic Piazza Grande sitting on an angle.

Every first Sunday of the month and the Saturday before, the extraordinary settings of piazza San Francesco, Piazza Grande and the Logge Vasari, the very heart of Arezzo, fill with stands, antiques dealers, collectors, tourists and all those curious to see the event.

Siena - on the way to Florence. Recommended hotel - Grand Hotel Continental Siena
Perugia - famous for chocolate, across the border in Umbria
San Quirico d' Orcia & La Foce Cypress Road

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Further recommendations

Cortona

Cortona’s appeal lies in its lofty setting, splendid views and medieval mood. Set close to the Umbrian border, 30 km south of Arezzo, Cortona is one of the most delightful hill towns in Tuscany. It was founded by the Etruscans, colonised by the Romans, and, after its sale to the Florentines in 1409, thrived under the Grand Duchy of Tuscany. Cortona is perched majestically on a ridge of Monte Sant’Egidio, dominating the Val di Chiana. The approach road winds through terraced olive groves and vineyards, past villas, farms and monasteries.

Cortona is a tourism hotspot so its over-popularity is a given. The city’s slow burn was accelerated after the town found fame in Under the Tuscan Sun, a book which led to a film and a summer festival.

Recommended restaurant - Ristorante La Loggetta

Monticchiello

Monticchiello is at its best in the summer when you can watch a performance of the town’s outdoor theatre and have dinner on a patio that spills into one of the village’s cobblestone streets. You’ll see the most visitors in the summer, and it’s when the village is most alive.

Monticchiello doesn’t have anything major to ‘check off your list.’ Instead, it’s a place to wander, admire the small cobblestone streets, take in the views of the Val d’Orcia, and enjoy some local food and wine.

The teatro povero (literally ‘poor theatre’) is one of the most interesting and unique things about Monticchiello, maybe you'll be lucky to catch a show: https://teatropovero.it