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.

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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.

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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.

The walks

The walks

This is a Grade 2 walk. The walks are from 10 to 12 kilometres and take between 3 to 4 hours. 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.  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 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 and wine

The food and wine

The traditional dishes of Tuscany are Italy's most influential cuisine.  The ingredients and techniques of the region have made their mark not just on the menus of the rest of Italy but also abroad, even in France.  The produce is of the highest quality, with its mushrooms, truffles and prosciutto especially prized.  Wine has always been central to Tuscany's economy and way of life, familiar names like Chianti and Brunello are just a portion of their enormous output.

Generous breakfasts are included each day (you'll need them for your walks).  Hidden Italy will provide you with a curated list with descriptions and locations of three to four restaurants for each town/village you visit (from fancy to more relaxed).  This information will be on the Hidden Italy walking App and you will be able to book your meals directly through the App.

Support on the walk

Support on the walk

To guide you through this wonderful walk, you will receive:  the Hidden Italy roadbook (an eighty-page A5 booklet that includes comprehensive daily walking notes accompanied by detailed maps, updated and revised each year);  access to the exclusive Hidden Italy App to complement the roadbook (the App is downloadable to Apple and Android devices and features information about the routes: maps, GPS tracks, altimetric profiles, etc; GPS navigation on all the routes; an alert function if you stray off the track; and an emergency function);  twenty-four-hour phone support from our Florence-based Operations Manager.

Booking conditions

To confirm the booking, a deposit of 25% of the total booking cost is required within 7 days of the issue of the invoice.  Please note that in the event of customer cancellation, deposits are refunded, less a cancellation fee of $500 per person per tour.  Click here for full T&C’s

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 included
  • Reading lists and historical and cultural notes
  • Maps and detailed walking instructions
  • Hidden Italy App with GPS to complement the roadbook
  • 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
  • City taxes are not included in the cost of the tour 

Cost Options

$2750 b&b per person

Single supplement:  $800

** Please note a high season surcharge may apply.

Tour costs quoted are in Australian dollars (AUD)




"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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