Day Walks in Tuscany

Caspin Journeys - unique walking holidays in Italy and England

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Montepulciano - Montichiello - Pienza

We wind through the streets of Montepulciano, known as the pearl of the Renaissance, admiring its wonderful buildings .We then visit the Cantina del Redi, where Vino Nobile is aged in vaulted caves beneath the foundations of the city. We leave through the ancient gates, passing the church of San Biagio and walk through picturesque countryside to Montichiello. Time to explore this tiny hamlet before continuing to Pienza a marvel of the 15thC, completely rebuilt by Pope Pius II to create the setting for a utopian society, which we can admire today.

Walking – 5hrs moderate-strenuous


Montefollonico - Montepulciano

We begin our walk at the fortified village of Montefollonico standing on a ridge between the Val D’Orcia & Val di Chiana. After enjoying its sleepy atmosphere, we leave through thick oak woods and descend gradually, emerging into an open landscape of cultivated fields, pretty vineyards and rolling hills. We have magnificent views as we approach Montepulciano, passing the Tempio of San Biagio, one of the great churches of the high Renaissance and enter town through one of its ancient gates.

Walking – 5hrs moderate


Montalcino - S Antimo - Bagno Vignoni

The walled hill-town of Montalcino, famous for its Brunello wine, is our starting point today. After a short visit of the town we make our way to the battlements of the Rocca castle for magnificent views of the Val D’Orcia. A few miles down the valley is the beautiful 8thC Romanesque abbey of Sant’Antimo and the start of our walk where we ascend a trail lined with cypress & oak. We continue our walk to the Castello di Ripa D’Orcia and end with a swim at the restorative hot springs of the charming hamlet of Bagno Vignoni.

Walking – 5hrs moderate-strenuous


Monte Oliveto - S. Giovanni d’Asso

A spectacular drive through the crete senese landscape takes us to the Bendictine abbey of Monte Oliveto. Guided tour of the amazing 16thC frescoes by Sodoma & Signorelli telling the story of St Benedict. Our walk offers gorgeous views of a very different countryside as we walk up to the little village of Chiusure with a wonderful opportunity to look back at Monte Oliveto standing in the midst of tall cypresses. Our walk continues on along a ridge until we reach San Giovanni d’Asso.

Walking – 3hrs easy-moderate


Castello di Brolio circular walk

This wonderful walk takes us through some of the most delicately attractive countryside in Chianti, to one of the most impressive castles in Tuscany, the home of the Ricasoli family since 1067 when they bought it from the Vallombrosan monks. Bettino Ricasoli, who died in 1880, was responsible for the blend of grapes that gave us Chianti Classico and the second Prime Minister of united Italy. The magnificent views from here stretch to Monte Amiata, Siena and beyond. A gloriously photogenic area, we walk through some of the most serious wine country in Italy.

Walking – 3hrs easy-moderate