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Panoramic roads in Tuscany: 5 must-see itineraries
A brief guide for discovering unforgettable views of impressive landscapes

“The meaning of seeking is in the journey, not the destination. The goal of travelling is travelling itself, not getting there.” (Tiziano Terzani)

These words by Tiziano Terzani take on a new meaning when evaluating how to travel in Tuscany. We usually open our maps and point to villages, cities, towns. We pin mental flags to it mark where we want to go but we often don’t consider the journey, or should we say, the inspiring panoramic roads to get there, all of which are picture-perfect. Tuscany’s roads offer unforgettable views of impressive landscapes and deserve a special mention, travel story in and of itself. Here is a list of five trips to jot down in your notebooks.

Viale dei Cipressi in Bolgheri
Viale dei Cipressi
Viale dei Cipressi- Credit:  Elena Tedeschi

"I cipressi che a Bolgheri alti e schietti van da San Guido in duplice filar / Quasi in corsa giganti giovinetti, Mi balzarono incontro e mi guardar."

Famous poet Giosuè Carducci introduced the world to the beautiful of the Viale dei Cipressi in Bolgheri, a breath-taking road that runs between the town of San Guido, in the province of Livorno, to the medieval village. This 4.7-km stretch of road was beloved by the poet and the thousands of tourists who travel along it every year, their admiring eyes fixed on the many trees that flank the way. You can travel the Viale dei Cipressi by car, on motorcycle or on foot before resting in the piazza in Bolgheri or taking a tour of the wine bars to taste delicious cheeses and a glass of red.

Il Romito
Il Romito
Il Romito- Credit:  Elena Tedeschi

The objective beauty of the views characterizing this stretch of coastal road known as Il Romito would impress even the most disenchanted traveler. Il Romito runs between the centre of Livorno and Cecina when coming from the north, and in 1962, the final scene of Dino Risi’s Il Sorpasso was filmed on it. In the movie, a young Vittorio Gassman is driving in a Lancia Aurelia B 24 before it skids off the cliff. Indeed, a portion of this road is all cliffs and castles, which were historically used as lookouts, as well as rocky bays where you can take a dip in the water after a day of snorkeling, enjoying the sunset with a view of the islands in the Tuscan Archipelago.

Down towards Bagno Vignoni
Bagni di San Filippo
Bagni di San Filippo- Credit:  Elena Tedeschi

Let’s head towards the silent, rolling hills found inland. Choose one of the trails that go up and down Monte Amiata, like Strada Provinciale 61, which leads to Bagni di San Filippo, home to free hot springs surrounded by forests. From there, you can reach the town of Bagno Vignoni, whose central piazza conserves a large well, and Pienza. Come here in the late autumn, when the hills are tinted with the colours of this magical season and the air smells of chestnuts, wine and freshly-pressed olive oil.

Fantiscritti Quarries
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- Credit:  Elena Tedeschi

The trails in this area are much less known by international tourists, offering a somewhat secret side of Tuscany, characterized by dark mountains and labour, tunnels dug into the rockface and views of the Carrara marble quarries. You can traverse the trail that starts at the Fantiscritti Quarries: from here, you can go inside the marble quarries and look out from the Ponti di Vara, the main railroad once used to transport marble, connecting the quarries with the port in marina di Carrara. Park your car, take photos and head deep into the mountain with an expert guide.

Chiusure and areas around Asciano
Chiusure and areas around Asciano
Chiusure and areas around Asciano- Credit:  Elena Tedeschi

Visit the village of Chiusure and the mystical Abbey of Monte Oliveto Maggiore before hopping in the car to visit the area around Asciano in search of side streets that lead to charming agritourisms, winding roads lined with cypress trees and the gold-hued Crete Senesi. The two roads I would recommend are the Strada Provinciale del Pecorile, boasting an unforgettable view, near the Agriturismo Baccoleno and the Strada Provinciale 438, which winds through the rolling hills as it runs between Asciano and Siena. Make sure you have your cameras on you!

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