Exploring Tuscan Hilltop Towns

Make your own way to Montepulciano. Standing high atop a hill in southern Tuscany, Montepulciano is a medieval town full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners. It boasts vast panoramas all over the wonderful Val d'Orcia and Val di Chiana valleys that surround it.

Starting from the San Biagio Church you follow a quiet track to the peaceful village of Montichiello where you can stop 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; a great spot to indulge in Tuscan treats! Distance 13km/8mi; Ascent 385m/1263ft, descent 505m/1657ft, Surf/Unsurf 20/80%

Today you wander through rolling hills, oak woods, cypress trees and pretty villages. From the start of the walk you will have views across the valley. Descend before climbing up to the town of San Quirico d' Orcia, a walled city with a 12th century church. Make your way to the village of Bagno Vignoni with its thermal hot springs. Distance 12km/7.5mi; Ascent 200m/656ft, descent 420m/1378ft, Surf/Unsurf 11/89%

You will be transferred from Bagno Vignoni to Castelnuovo dell'Abate. As you arrive in the village, you will enjoy the stunning beauty of Sant'Antimo Abbey, a former Benedectine monastery dating back to the 8th century A.C. The first section of the walk to Montalcino will bring you to some panoramic views overlooking the beautiful Orcia Valley. Prepare for some exquisite local wines as you arrive in Montalcino. Distance: 13km/8mi Ascent: 450m/1476ft, descent: 280m/918ft: Surf/Unsurf 14/86%

A hearty breakfast will set you up for an enjoyable day of walking in the famous Brunello wine region, passing vineyards and olive groves, then again entering the beautiful Tuscan landscape of the Crete Sensi and Buonconvento. Depending on accommodation booked, you will either spend two nights in Pieve a Salti (shuttle service available for transfer to/from the restaurant for dinner) or Buonconvento. Distance 15 or 18km/9 or 11mi; Ascent: 315m/1033ft, descent: 620m/2034ft: Surf/Unsurf 23/77%

After breakfast transfer to the monastery at Monte Oliveto Maggiore. Begin your walk at the watchtower and make your way to the little village of Chiusure. Pass farmhouses along the way. Once again this walk provides great views of the Crete Senesi landscapes. Return to your previous nights accommodation. Distance: 14km/8.5mi Ascent: 380m/1247ft, descent: 460m/1510ft: Surf/Unsurf: 23/77%

Today you will start with a short transfer to Monteroni d’Arbia from where you start the walk towards Siena. Hike through a landscape of rolling hills and small hamlets as the unmistakable sight of Siena appears in the distance. Once you reach Arbia train station take the train into Siena. *Option to pre-book a vehicle transfer to Siena (additional cost)* Enjoy the magnificent beauty of Siena, famous for its biannual “Palio” horse race, held in the most beautiful shell-shaped square in Europe: the Piazza del Campo. Don’t miss a visit to the Duomo, an architectural treasure, and numerous imposing medieval palaces. Distance: 10km/6.2mi, Ascent: 230m/755ft, descent: 190m/623ft, Surf/Unsurf: 15/85%