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:

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.

Please note, the viticultural traditions of Montalcino can be experienced at an organic vineyard a short walk (or drive) from your accommodation on Day 2.  This includes a guided vineyard visit plus a variety of tasting in the cellars: 'Welcome to Montalcino' (3 wines, 1.5 hours), 'Terroir Experience' (5 wines, 2 hours); and 'Vertical Tasting' (6 wines, 2.5 hours).  Please contact us for details.

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:

We require a $500 per person non-refundable deposit to confirm the booking.  Should government COVID-19 travel restrictions prevent the tour from operating, the tour will be rescheduled.  In the event the new dates are not suitable, you will have the option of a credit note for the amount paid which can be used towards future tours or a full refund, minus the deposit which will be held as credit for future tours.  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
  • 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

$1995 B&B only p/p


$2260 with dinners included p/p

Single supplement:  $600




"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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