8 days
Easy to Moderate

  Explore the charming Medieval and Renaissance villages of Tuscany’s beautiful Val d’Orcia region

  Hike amid the characteristic Tuscan landscape of rolling hills, olive groves and vineyards

  Enjoy the world-famous local wines and let your senses be seduced by the delicious Tuscan cuisine

  Relax and feel the healing power of the warm underground springs in Bagno Vignoni

  Visit the impressive Benedictine monastery Monte Oliveto Maggiore, beautifully located on a wooded peak

Hiking in the Val d’Orcia

Discover the hilltop towns of Tuscany

Soft rolling hills, cypress alleys, golden wheat fields, silver green olive groves and straight-lined vineyards surrounded by wooded mountain ranges to the north and small islands lying like pearls in the glittering blue sea to the south. Add to this an exceptional kitchen and some equally exceptional wines, historical towns and a rich cultural heritage – then you have Tuscany!

On this 8 day self-guided hiking trip you will walk in the Val d’Orcia. This beautiful part of Tuscany stretches for about 80 km, from Siena in the north to the great volcano Amiata in the south. Val d’Orcia was added to the UNESCO list of World Heritage Sites in 2004 and if you want to experience the classic Tuscany landscapes that you know from renaissance paintings, postcards and films such as Gladiator, The English Patient and A Midsummer Night’s Dream then this is the place to go!

With its lyrical landscapes, world-class art and a superb cucina contadina (farmer’s kitchen), the Tuscan experience is perfectly in symbiosis with the land. – Lonely Planet

The soft, fertile landscape is tied together by the hilltops’ medieval stone villages, and it is between these charming hamlets that you will hike. You will stay in the two cosy villages of Montepulciano and Montalcino, both producers of world-famous wines, and in the beautiful UNESCO town Pienza, which offers unique renaissance architecture and an unsurpassed view of the valley. You will also pass Bagno Vignoni where you can relax in the thermal baths supplied with water from the warm, underground springs.

It is hardly necessary to mention that both the food and the wine in this region is in a class of its own, so when the day’s hike is over you can look forward to spoiling your taste buds with an exquisite Tuscan dinner.

8 DAYS / 7 NIGHTS €850 per person sharing*

*Discounts available for triple rooms. Please enquire for prices.
*A single supplement fee will apply to solo walkers

ACCOMMODATION In 3* and hotels and agriturismo on a bed & breakfast basis. All rooms are en-suite.
You can book additional night(s) at any of the accommodations along the way.
AVAILABILITY You can start on any day of the week, subject to availability, between April and October
7 x nights in selected B&Bs, hotels and agriturismo
7 x Breakfasts
Luggage transfers while you walk
Private transfer on Day 4, Day 6 and Day 7
Detailed route notes and maps with tracks on
Pre-departure information pack
24/7 telephone support
Flights & travel insurance
Lunches & dinners if not specifically mentioned above
Travel to Montepulciano and from Siena
Personal expenses (drinks, phone calls, tips, etc.)

Day 1: Arrive in Montepulciano

Your hiking holiday in Tuscany starts in the wine town of Montepulciano. Situated high on a hilltop with medieval architecture and steep streets, the little town reeks of historical charm. Getting to Montepulciano is easy; from either Rome, Florence or Pisa you can take the train to Chiusi and from there a local bus or taxi. When you have arrived we recommended taking a seat in one of the many lovely wine bars and enjoy a glass of local red while enjoying the impressive view over the hilly Tuscan landscape that you will soon explore on foot.

Overnight: Montepulciano


Day 2: Montepulciano to Pienza

Distance: 13/15 km | Ascent: 384 m | Descent: 504 m | Time: 4 hrs approx.

Starting from the church San Biagio you follow a quiet path with great views through undulating landscapes, passing wineries, vineyards and olive groves galore. After a while you reach the peaceful village of Montichiello where you can stop for lunch or a quick cappuccino before continuing to Pienza.

Pienza has been a popular destination since the 1400s and the pope palace, the cathedral and the gardens still look like they did in the Renaissance. The town, known for its truffles and delicious pecorino cheese, is a great place to sample some of the many Tuscan delicacies. The view over Val d’Orcia from the town walls is spectacular!

Overnight: Pienza


Day 3: Pienza to Bagno Vignoni

Distance: 12 km | Ascent: 197 m | Descent: 418 m | Time: 4 hrs approx.

This day you will be walking through a beautiful area of soft hills, oak forests, cypress trees and pretty villages. In Bagno Vignoni you can spend the afternoon relaxing in the thermal baths that get its warm water directly from the town’s underground springs. People have benefited from the healing power of this water since the Roman times, and it is perfect for tender legs and feet.

Overnight: Bagno Vignoni


Day 4: Bagno Vignoni to Sant'Antimo

Distance: 14 km | Ascent: 227 m | Descent: 187 m | Time: 5 hrs approx.

This is a more challenging, although rewarding day where you follow dried-up river beds through wild surroundings to Sant’Atimo; an isolated monastery in an idyllic landscape. When you have explored the monastery you will get a transfer to Montalcino where your next accommodation awaits.

Montalcino is situated about 750 metres above the sea and there’s a fine view over the surrounding area from there. The world-famous wine Brunello di Montalcino is produced here, and in the historic centre you will find several wine cellars, craft workshops, charming cafés and shops selling local specialties such as honey and ‘ossi di morto’ biscuits.

Overnight: Montalcino


Day 5: Montalcino to Buonconvento

Distance: 15/18 km | Ascent: 316 m | Descent: 619 m | Time: 5 hrs approx.

A hearty breakfast will set you up for a long but enjoyable day of walking in the famous Brunello wine region, passing vineyards and olive groves, then again entering the beautiful Tuscan landscape of the Crete Sensi and Buonconvento.

Overnight: Buonconvento


Day 6: Monte Oliveto Maggiore to Buonconvento

Distance: 14 km | Ascent: 382 m | Descent: 460 m | Time: 5 hrs approx.

You start the day with a short transfer to the Benedictine monastery Monte Oliveto Maggiore situated high on a wooded peak in lonely majesty. The monastery was founded in the beginning of the 14th century and quickly obtained a great reputation due to its many prominent religious personalities. Most of the impressive complex dates back to the 15th and 16th centuries and today it is home to one of the largest and most active Benedictine assemblies. The monastery’s church is open to visitors and there is also a small restaurant, a café and a souvenir shop run by the monks.

When you have finished exploring the monastery you walk back through a beautiful, undulating landscape passing the village of Chiusure en route. The track also leads you through a wooded area and once again you will have some lovely views over the Crete Senesi landscape before reaching Bunconvento once again.

Overnight: Buonconvento


Day 7: Monteroni d’Arbia to Siena

Distance: 10 km | Ascent: 227 | Descent: 187 m | Time: 4 hrs approx.

You start your last day of hiking with a transfer to Monteroni d’Arbia from where you start your walk towards Siena. The route traverses a hilly terrain with several villages along the way. When you reach Arbia you take the train to Siena; a beautiful and historically interesting town that you have plenty of time to explore.

Overnight: Siena


Day 8: Arrivederci Tuscany!

Your Val d’Orcia hiking holiday has come to an end. From Siena there are good train connections to Rome, Pisa and Florence.

Getting to Montepulciano

  We recommend flying to PisaFlorence or Rome.
/ From the city centre railway station in either of the three cities you can catch a train to Chiusi and continue from there with a local bus or taxi to Montepulciano (25 mins). Approx. journey times to Montepulciano; Pisa 2h50-3h20, Florence 1h50-2h15, Rome 1h50-3h15.

Visit www.trenitalia.it for times, prices and booking. Tickets can be purchased on arrival or online prior to departure.

Departure from Siena

  From Siena you can take the train back to Pisa (2h00-3h15), Florence (2h15-3h15) or Rome (2h15-3h20). Again, please see Trenitalia’s website for timetable planning.
  We will send you a pre-departure information pack, which contains detailed public transport information.
Val d'Orcia Montepulciano walking holiday
Hiker in the medieval hilltop village of Montepulciano
The rooftops of Montepulciano
Walking to the Templo di San Biagio
View over the beautiful Val d'Orcia countryside from Montepulciano
Hiking towards the hilltop village of Pienza
Staircase in Pienza
Hiking trail from Pienza
Hiking in the Val d'Orcia towards Bagno Vignoni
Cappella di Vitaletta
Val d'Orcia countryside near Bagno Vignoni
Hiking trail in the Val d'Orcia
Signpost for Bagno Vignoni
Bagno Vignoni
Castello di Ripa d'Orcia
Mastrojani vineyards, Ripa d'Orcia
The Abbey of Sant'Animo
Wine tasting at the Abbazia di Sant'Animo
Montalcino Fortress
View from Montalcino Fortress
Monte Oliveto Maggiore Monastery
The stunning hilltop city of Siena
The Piazza del Campo, Siena

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