Starting from the San Biagio church, follow a quiet dirt road to the enchanting village of Monticchiello, perched on a hill and known as the balcony of the Val d'Orcia. Pause for a cappuccino before continuing to Pienza. A UNESCO World Heritage site, Pienza is famous for its unique Renaissance architecture and delicious pecorino cheese.

Today’s route is classic Tuscany, taking you through rolling hills lined with cypress trees to the tiny medieval town of San Quirico d'Orcia, located on the old Via Francigena pilgrim route. Continue to the highly picturesque village of Bagno Vignoni, famous for its Roman and Renaissance thermal baths.

Walk in and out of woods to reach the Benedictine Monastery of Sant'Antimo, an extraordinary example of Romanesque architecture where monks sing Gregorian chants. After exploring, you will be transferred to Montalcino. Dominated by a mighty fortress built in 1361, Montalcino offers spectacular views stretching across the Val d'Orcia toward Monte Amiata and Siena.

Prepare for a fairly tough day of walking through the famous Brunello wine region. You will pass through vineyards and olive groves before entering the beautiful Tuscan landscape of the "Crete". Arrive in Buonconvento, where you will spend the night in a lovely rural agriturismo.

Enjoy a short day full of ups and downs. Start with a transfer to Monte Oliveto Maggiore, an impressive red-brick abbey set in the rugged landscape, visiting early to avoid crowds. Walk back to Buonconvento, followed by an afternoon transfer to your centrally located hotel in the magnificent city of Siena.

Spend the day exploring Siena, one of Europe's best-preserved medieval cities. At 11:00 am, join an included 90-minute guided walking tour of main attractions like the Basilica of San Domenico and the magnificent Duomo Cathedral (exterior). Alternatively, join a 90-minute guided Sienese food and Chianti wine tasting tour. Spend your afternoon wandering cobbled streets and people-watching at the famous Il Campo square.