Hill Top Towns of Tuscany

Starting from the San Biagio church you will follow a quiet trail to the peaceful village of Monticchiello where you can take a break for a relaxed lunch or perhaps just a quick cappuccino before continuing to Pienza. Pienza is a UNESCO World Heritage site with unique Renaissance architecture. The town is well known for its delicious pecorino cheese and truffles; this is a great spot to indulge in local Tuscan treats!

Today’s route takes you through a beautiful region of rolling hills, oak woods, cypress trees and pretty villages. The thermal baths and complex at Bagno Vignoni sitting on a hill above Val D’Orcia it is the perfect location to spend the afternoon soaking up the Tuscan warmth.  Perhaps a visit to the Old Baths of St. Catherine or the church of St. John the Baptist.

Today first we have a transfer to Castelnuovo where we start the walk mainly on wide dirt roads. Before starting your walk visit the stunning abbey of Sant’Antimo. This is a former Benedictine Monastery which dates from the 8th century. During the walk, you will have many stunning panoramic landscapes to admire across the Orca Valley. In Montalcino why not enjoy one of the fine local wines famous from this region?

A hearty breakfast will set you up for a long but enjoyable day of walking in the famous Brunello wine region. In the first part of today’s walk you will pass through the many vineyards and olive groves; before later entering the beautiful Tuscan landscape of the Crete Sensi and Buonconvento.  Buonconvento is widely regarded as one of the most beautiful towns in Tuscany, if not Italy. 

A short day which is full of ups and downs, beginning with a transfer to the monastery at Monte Oliveto Maggiore, an impressive abbey built of red brick and set in the rugged Tuscan landscape, with its Benedictine Monastery and Museum. After an early visit to avoid the crowd, walk back to Buonconvento.

Today will start with a short transfer to Monteroni d’Arbia from where you start your walk to Siena. Hiking through a landscape of rolling hills and small hamlets as the unmistakable sight of Siena appears in the distance. Enter the town through Porta Romana, one of the medieval gates and walk through the city to reach your hotel.

Once you reach Arbia train station take the train into Siena. Take in the sites of this quintessential Italian city, enjoying a refreshment in the Piazza del Campo or take a stroll along the many quaint streets around Siena Cathedral. 

Depart after breakfast.