Montalcino to Montepulciano, Italy

You will need a day-pack to carry all essentials such as water and sunscreen, as all of your large baggage will be transported for you, each day.

Montalcino and Montepulciano are famous for their wines, however the area that lies between them is the UNESCO listed valley (Val d’ Orcia).

Val d Orcia – UNESCO Justification for Inscription
Criterion (iv): The Val d’Orcia is an exceptional reflection of the way the landscape was re-written in Renaissance times to reflect the ideals of good governance and to create an aesthetically pleasing pictures.

Criterion (vi): The landscape of the Val d’Orcia was celebrated by painters from the Siennese School, which flourished during the Renaissance. Images of the Val d’Orcia, and particularly depictions of landscapes where people are depicted as living in harmony with nature, have come to be seen as icons of the Renaissance and have profoundly influenced the development of landscape thinking.

Day 1 – Pick up from your Hotel in Siena (the night in Siena is at your own cost). Your group and baggage are transported to Montalcino mid morning, allowing you a full afternoon to explore the famous wine town of Montalcino with it’s medieval castle, which stands over the small town.

Day 2 – Has you walking though the Val d’ Orcia (you would have had wonderful views of the valley during the previous day and night from the height of Montalcino). Today’s walk will take between 2.5 and 3.5 hours, depending on how many times you stop to enjoy or photograph the scenery.

Your destination is the little town of San Quirico. You should arrive there with plenty of time to have lunch and explore the small village prior to checking into your accommodation. You will be staying in San Quirico for two nights.

Day 3 – A short walk today of 1.5 hours to Bagno Vignoni with a pick-up option available to deliver you back to San Quirico, or alternatively, you can walk back to San Quirico. Bagno Vignoni is a beautiful little town with a history around milling and hot water baths.

Day 4 – Today you walk to the lovely little medieval town of Pienza. Today’s walk will take between 3 to 4 hours. Spend the afternoon exploring the little town, but make sure you spend some time enjoying the Italian life in the Piazza later on in the evening.

Day 5 – We have left the longest walk to last, with an option to reduce it if required. The walk from Pienza to Montepulciano can take up to 4.5 hours, when you include a lunch stop at beautiful little hill top town of Montilcchello. This adds approximately 40 to 50 minutes walking to the day, but it is worth it to see the little town and enjoy the views whilst having an authentic Italian lunch. After lunch it’s time to walk to Montepulciano, the largest of the towns on this walk. Famous again, for their wine Montepulciano sits atop a large hill and has commanding views as you walk towards the medieval town. Montepulciano is famous for the many music festivals as well as the annual wine barrel rolling festival (Bravìo delle Botti). Enjoy the many wine tastings (Enotica – Italian for Wine Shop) and historical buildings of Montepulciano. The last section of the walk today is steep, but worth the trip to the magnificent Montepulciano.

Day 6 – No more walking today. Still some time to explore Montepulciano in the morning before your group is picked up from your Hotel and driven to Chuisi Railway Station. Trains from Chiusi will take you to most major cities, North and South, to enable you to continue your journey within Italy or beyond.

What’s included:

  • Detailed Route Notes
  • Tour is exclusive to your group
  • Information on the Villages/Towns/Cities and surrounding area
  • Accommodation
  • Luggage transfers
  • Transportation from Major City Transport Hub
  • Any scheduled transfers as per Trip Notes
  • Emergency support
  • Breakfasts

What’s not included:

  • Lunch and Dinner
  • Any entrance/park fees
  • Travel insurance
  • Personal expenses along the way
  • Unscheduled transfers required during the trip
2021 costs will be provided once confirmation that current travel restrictions has been lifted.
Tour Dates to be advised once COVID restrictions are lifted and we have a clearer indication of when travel can resume.
This Tour is a Grade 3 Walk Rating

g1Grade 1
No bush walking experience required. Flat even surface with no steps or steep sections. Suitable for wheelchair users who have someone to assist them. Walks no greater than 5km.

g2Grade 2
No bush walking experience required. The track is a hardened or compacted surface and may have a gentle hill section or sections and occasional steps. Walks no greater than 10km.

g3Grade 3
Suitable for most ages and fitness levels.
Some bush walking experience recommended. Tracks may have short steep hill sections a rough surface and many steps. Walks up to 20km.

g4Grade 4
Bush walking experience recommended. Tracks may be long, rough and very steep. Directional signage may be limited.

g5Grade 5
Very experienced bush walkers with specialised skills, including navigation and emergency first aid. Tracks are likely to be very rough, very steep and unmarked. Walks may be more than 20km.

Review of This Walk

“The gentle undulation of the Tuscany landscape along with the beautiful history of its towns made this self guided walk a delightful experience. The captivating scenery of sunflower crops, grape vines, olive trees and pencil pines occupied every corner and every hillside. The towns individually set upon the hill top with pebble paved roads, window shutters, buildings of stone were inviting me to experience the culture, history, food and the Italian people. I was charmed by the history, the warmth and the traditional “Siesta”, a truly charming time of day. With everything organised from maps, accommodation and luggage transfers, it was a wonderful and memorable holiday. Thank you Wayfarer Experiences. I will be back!”