Exploring Tuscan Hilltop Towns

Exploring Tuscan Hilltop Towns

Trip Highlights

  • Medieval villages & hilltop towns
  • Regional culinary specialities
  • Cypress lined hills & vineyards

Trip Summary

The Tuscan landscape of the Val d’Orcia will open your eyes to its natural beauty. This walk takes you along steep valleys, dense forests, rivers and the legendary “badlands” eroded clay slopes. Walk by quintessential farmhouses nestled amidst olive groves, vineyards and fig trees on your way to the hot spring hamlet of Bagno Vignoni and the Renaissance city of Pienza. On this week long exploration, you will visit palaces, Romanesque churches, thermal baths, and wineries serving the divine local red “Brunello”.


Introductory to Moderate. There are nonetheless some steep and quite long hills, some fairly steep but short descents and some paths with rough gravel, stony and occasionally muddy surfaces. Fitness: High standard of fitness is not necessary but clients should be able to walk for up to 7 hours a day in hot sun on dusty or stony tracks.


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.

Meals:  Nil

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!

Meals:  B

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.

Meals:  B

A challenging but rewarding day’s walking awaits as you follow dry riverbeds through a fairly wild environment to Sant’Antimo, an isolated abbey situated in a Pastoral landscape. After exploring the impressive abbey you will be transferred to Montalcino for your overnight accommodation.

Meals:  B

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 accomodation booked, you will either spend two nights in Pieve a Salti or Buonconvento

Meals:  B,D

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 and once more this walk provides great views of the Crete Senesi landscapes. As you get close to Pieve a Salti you can see views of it to the right on a ridge as you walk. Save some energy for the last kilometre as you have to climb steeply to get back to your accommodation.

Meals:  B,D

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. 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.

Meals:  B

After breakfast, make your way to the train station for your onward journey or book an extra night to spead more time exploring this wonderful city.

Meals:  B

What's Included

  • 7 breakfasts, 2 dinners
  • 7 nights in 3-4 star hotels & agriturismo
  • Vehicle transfers day 4,6 & 7
  • Luggage transfer (1 bag per person not weighing anymore than 20kg)
  • Information pack including route notes & maps
  • GPX tracks
  • Emergency hotline

What's Not Included

  • 5 evening meals, all lunches & beverages
  • Entrance fees
  • Travel insurance
  • Travel to the start and from the end point of the trip
  • Personal expenses such as laundry and phone calls
  • Tourist taxes €1.00 - €2.50 per night

Upcoming Travel Dates


Duration:8 Days
Starting Point:Montepulciano
Finishing Point:Siena
Activities:self-guided walking
Grade:moderate  Click for more information
Trip Code:JTM
Prices From:GBP£1050 Per Person
Single Supplement:GBP£220  Click for more information
Solo Traveller:GBP£430  Click for more information
Please do not book any flights or extra arrangements until such time that your booking is confirmed by Sherpa Expeditions by phone or email.