Tuscany Val d'Orcia walk

Starting with a private transfer to the charming medieval town of Montalcino, this walk tour crosses the Orcia River Valley in southern Tuscany, passing through some of the most beautiful country in central Italy.

Leaving the medieval walls of Montalcino, four days later you'll finish in Montepulciano, having passed through an area as famous for its rolling hills, wheat fields dotted with red brick farmhouses, stands of deep green cypress pines and endless views, as it is famous for its wines and food.

tuscany strip 1

The Via Francigena was the medieval road that bisected the valley and was for several centuries the principal way linking Papal Rome with northern Europe, carrying pilgrims, traders, Crusader armies, emperors and popes. It is lined with castles, monasteries and villages that date from this period. Most of the paths and thoroughfares that you follow also date from the era.

Along the way you stay in some of the cultural treasures of southern Tuscany: a beautifully restored pilgrim town with a large pedestrian centre; a magnificent papal town and Montepulciano, 'pearl of the Renaissance'.

The walks

The walks

This is a Grade 1 walk (click here for details).  The walks are from 10 to 12 kilometres and take between 3 to 4 hours and will leave you plenty of time to explore the gorgeous places you'll be staying in.  They are well marked and generally follow good, unsealed country roads through undulating hills.  There are several rougher sections but the trails are easy to follow.  The walk is suitable throughout the year.

The self-guided itineraries are rewalked and the notes updated each year.

The accommodation

The accommodation

Hidden Italy uses the best accommodation available.  On this tour all the accommodation is in  family-run, three star hotels which are based in centrally located, restored heritage buildings which themselves are part of the the local history.  The exception is Day 2 when you'll stay in a private serviced apartment in the centre of a tiny medieval village (there are no hotels here).

The food

The food

Generous breakfasts are included each day (you'll need them for your walks).  With notice, the hotels wil be able to prepare a cut lunch for the walk.  The Val d'Orcia is celebrated for its wines (eg Brunello and Vino Nobile) as well as its classic cuisine: pastas, soups, meats, cheeses, frsh vegatables.... Dinners are not included in the standard tour, however, if you select the 'Dinners option' (which we recommend) this will include 3 course meals alla carte in some of the finest restaurants in the area.  The dinner option also means you'll have a guaranteed booking each night.

Guided city tours of Siena and Florence

My friend and colleague Anna, the Hidden Italy operations manager, is a fully qualified guide for both Siena and Florence and is now available for private tours to these two extraordinary cities.  If you would like to book a tour, email: info@hiddenitaly.com.au.  Click here for a profile of Anna.

"But most of all Anna is marvelous - such an excellent guide and companion. She brings the history to life and she is a lovely, lovely woman."  Melissa and Bob C (Florence and Siena).

Interested in the 2. Central Italy: Tuscany 1, from Montalcino to Montepulciano Self-Guided Walk?

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This 6 day walk can be personalised to meet your interests and dates.

  • Cost


    per person
  • Five nights accommodation
  • all breakfasts
  • reading lists and historical and cultural notes
  • maps and detailed walking instructions
  • daily transfers of baggage between hotels
  • pick up at either Siena or Chiusi (on the Rome/Florence rail line) and drop-off at the end back in Chiusi
  • 24 hour backup from local manager

Cost Options

$1840 b&b or $2100 with dinners included

Single supplement:  $550

Montalcino Wine and Cooking Option - $990 per person

5% discount when 4 people or more book and deposit together.



"I'm back from my holiday and back at work! My walk from Montalcino to Montepulciano was marvellous and, given the opportunity, I'd do it again tomorrow! I've certainly told friends what a great time I had and would recommend it to anyone."

– Bridget N, Tuscany 1 walk

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2. Central Italy: Tuscany 1, from Montalcino to Montepulciano FAQs

Find out a little more about the 2. Central Italy: Tuscany 1, from Montalcino to Montepulciano tour by reading some of our most frequently asked questions.

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2. Central Italy: Tuscany 1, from Montalcino to Montepulciano

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