Walking Italy’s Rural Heartland

Italy’s rural heartland is best discovered on foot, where after a day spent trekking through the natural beauty of the regions hilltop towns and forests. This is a region celebrated for the uncompromising quality of its wine and local cuisine, where you can take time to explore the area’s historic towns and culinary specialties. In 2004, the Val d’Orcia was inducted into the UNESCO list of World Heritage Sites for the historic and cultural significance of the landscape.


  • See the beautiful Tuscan landscape up close and on foot, passing vineyards and olive groves of the Brunello wine region (with opportunities en route to sample the Brunello local red)
  • Walking through classic Tuscan scenery: gentle, rolling hills, broken by medieval and renaissance villages and hilltop towns
  • Stay in the beautiful Renaissance city of Pienza, a designated UNESCO world heritage site, where you can visit captivating palaces, Romanesque churches and Pienza Cathedral
  • Visit the historic red brick monastery of Monte Oliveto Maggiore en route
  • The famous medieval city of Siena, the capital of the province of Siena
  • Stay in ‘agriturismo’ farmhouses and the historic settings of the area’s medieval towns and villages

RouteVal d'Orcia
Duration7 nights/6 days walking
Length57.5 mi (78km)
GradeEasy to Moderate
AvailabilityApril - Oct
Price from£765
Holiday CodeITA-VDO

Why this walk?
Take a route through one of Tuscany’s six World Heritage Sites, designated for its influence and depiction in many paintings of the Renaissance era. The area is also renowned for its outstanding local produce, with festivals throughout the calendar celebrating some of Tuscany’s most popular culinary exports (such as truffles and Brunello wine). The Val d’Orcia denotes the valley around the river Orcia, a landscape popular among photographers, with vast, open vistas of rolling hills stretching far into the horizon. As you follow this route through the expansive countryside, you’ll find a scenery punctuated by the clusters of Cypress and vineyards on your way to the region’s beautiful Renaissance towns and villages.

The Path

The Val d’Orcia footpath meanders through gentle, rolling hills, the trail occasionally broken by short, soft ascents and descents through dried up ravines. This is a landscape made iconic through renaissance art and modern photography, a trail leading through famous, picturesque medieval towns and the farms and vineyards that gave the area its important gastronomic and cultural status - still very much in effect as you follow the Val d’Orcia through some of Tuscany's most beautiful stretches of countryside.

The Accommodation

Small, welcoming family-run hotels comprise the accommodation on this journey through the Tuscan countryside. This walking holiday also features the popular Italian institution of ‘Agriturismo’ accommodation, with B&Bs in old farmhouses.

Across the Val d'Orcia, the introduction of rooms and modifications for housing guests have been designed to reflect the original character of the building and locality. All rooms have en-suite facilities, breakfast included on all days and dinner included on two nights where there are no suitable alternative dining options readily available.

Hotel Balcony Tuscany

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Itinerary: Montepulciano to Siena

Days: 6 (7 nights)| Distance: 49 mi (79 km) | Difficulty: Easy to Moderate| Comfort: 3.5/4 | Price: from £805 p.p.

  • Day 1

    Arrival in Montepulciano

    Arrival in Montepulciano by train or bus, easily reached from Rome, Florence or Pisa; catch the train to Chiusi, then take the local bus or a short taxi ride into the town. However you choose to travel to Montepulciano, you're sure to get a glimpse of the rolling hills of the Tuscan countryside that you'll be exploring over the coming week.
  • Day 2

    Montepulciano to Pienza

    8.1 miles/ 13km

    Begin your walk at the San Bagio church, following rolling Tuscan countryside to the quaint, picturesque settings of Pienza, famous for its delicious pecorino cheese and truffles; very much worth a sample. There is an optional detour to the town of Monticchiello (+2km), a relaxed town, ideal for a coffee or bite to eat!
  • Day 3

    Pienza to Bagno Vignoni

    7.5 miles/12km

    A few gentle hills on this walk through a landscape dotted with cypress trees, oak woods and the walled, stone towers of the region’s pretty villages. End today’s walk in the thermal bath town of Bagno Vignoni.
  • Day 4

    Bagno Vignoni to Sant’Antimo, Transfer to Montalcino

    8.9 miles/14.3km

    A more challenging, but rewarding day following the dry riverbeds that comprise today’s walking route through the wilder, more rustic countryside outside of Bagno Vignoni to the isolated abbey of Sant’Atimo. After you’re finished exploring the abbey, a transfer awaits to take you to the hilltop town of Montalcino.
  • Day 5

    Montalcino to Pieve a Salti

    9.1 miles/ 14.6km

    * Please note dependent on accommodation availability this walk may be extended by 3km. Today’s walk takes place in the Brunello region, renowned for its fine wines. On your way through the beautiful Tuscan landscape of the Crete Sensi, you’ll pass vineyards and olive groves to Pieve a Salti, with a transfer to your accommodation in Buonconvento.
  • Day 6

    Transfer to Monte Oliveto Maggiore Monastery Walk to Pieve a Salti

    8.4 miles/ 14km

    The day begins with a transfer to the red brick monastery of Monte Oliveto Maggiore. This is a short, though fairly strenuous day involving a number of undulating gradients on your way back to Pieve a Salti through rugged Tuscan landscape. Transfer back to Buonconvento.
  • Day 7

    Walk Monteroni d’Arbia to Arbia

    7 miles/ 11.2km

    a.m. - Transfer to Monteroni d’Arbia The trail out of Monteroni d’Arbia winds its way around a classic Tuscan landscape of rolling hills and hamlets with panoramic views over the hills to the town of Siena beyond. There is a taxi transfer from Arbia to the famous town of Siena, preserved in its captivating medieval design. p.m. Transfer to accommodation in Siena

Click ' + ' signs to view a detailed daily breakdown

PricesSeason 1
01/04/18 – 31/10/18
Two people sharing (p.p.)£805
Single person in a party£1020
Solo person£1255
  • What's Included?

    Price Includes

    • 7 nights bed and breakfast
    • 2 dinners (Nights 5 & 6)
    • Luggage transfers and personal transfers to/from the path where necessary during the walking programme.
    • Destination Manual and Road Book (route notes) showing directions to your accommodations and two local maps.

    Price Does Not Include

    • City taxes (per person) only payable direct to accommodations – The prices below indicate the total to pay per person, rather than per night.

    Please consider city tax can vary during the year and new taxes can be introduced

    (Montepulciano 1€, Pienza 0,7€, Bagno Vignoni 0,7€, Montalcino 0,7€, Buonconvento 2€, Siena 2,5€)

    • Packed lunches (own arrangements)
    • Travel to Montepulciano / from Siena
    • Postage Overseas ~ £5.00 (Europe), £10.00 (Rest of the World) ~ per walk pack
  • Price Info

    Rest Days: Please enquire for extra night prices at each location

    Holiday arrival/departure dates:

    You choose which day you would like your holiday to start on. We will book your holiday in accordance with your requirements.

    Please check the dates and prices carefully before booking. We will book your holiday in accordance with your requirements. (Holiday runs between 01/04/18 – 31/10/18).

  • Getting There

    The Val d'Orcia is in proximity to the two major airports of Tuscany, but it can also be reached from two of Rome's airports, in the Lazio region.

    Florence “A Vespucci”             (FLR)                    http://www.aeroporto.firenze.it/en/

    Pisa                                         (PSA)               http://www.pisa-airport.com/en/                      

    Rome   Fiumicino                    (FCO)               http://www.adr.it/web/aeroporti-di-roma-en-

    Ciampino                    (CIA)

    You are responsible for booking your air travel to airports and onward travel to your first accommodation and from your accommodation on departure.

    From the airports you can take a train, and a connecting bus service to reach Montepulciano.

  • Best Time to Travel

    Visiting in Spring and Autumn is the best policy for avoiding the heat of high summer, which can make progress a lot harder out on the country tracks.


Enquire About Val d’Orcia

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