Walking the Val d'Orcia - from Siena to Montepulciano - TUS 4

Walking the Val d'Orcia - from Siena to Montepulciano
Comfort level
7 days - Bases in charming hotels & agriturismo’s
Starting from: € 715


This is a moderately easy tour which is suitable for those who have some experience with walking and a good general physical condition. Through the extensive footpath network of the area, roughly following the traces of the Via Francigena, one of Europe’s most important ‘high ways’ in medieval times, you walk from village to village, a full immersion in the world-famed Tuscan landscape.

It is a perfect introduction to the region and for people who love museums and galleries, Gothic and Romanesque architecture, there is plenty to see and do. You have plenty of time for attraction visits on most days.

You have the time to visit the beautiful historic towns of the Val d’Orcia: Montepulciano, San Quirico, Buonconvento, Bagno Vignoni and Pienza, arguably the most perfect Renaissance town of Tuscany. This tour threads together some of the most attractive towns and villages in Tuscany in an eloquent procession.

However the emphasis of the tour is to enjoy the countryside, the rolling vineyards, the poppies in spring and the wild cyclamen in autumn. Most of all, many of the views have changed little for hundreds of years.  South of Siena, you head off into a coffee table book Tuscan landscape of gentle hills, tipped by a lonely pine or oak tree while cypresses line the way leading to the distant farmhouses.

At first you walk through the spectacular rolling hills of the Crete Senesi, with its extensive fields of wheat and sunflowers, and finally the rolling hills of the Val d’Orcia, scattered with picturesque small towns. Walking here is an unforgettable experience!

You spend a night in one of the most beautiful convents of Tuscany at Monte Oliveto Maggiore. This is a typical red brick Monastery where friars of the Benedictine Order still worship. Staying overnight there is a memorable experience. The next historical villages are Buonconvento and Montalcino, surrounded by vineyards of San Giovese grapes, for the famous Brunello wine. Then you enter the Val d’Orcia, a unique landscape scattered with wonderful small towns; San Quirico, Pienza and Bagno Vignoni, with its unique town square:  a huge pool of healthy sulphurous water. Our tour finishes in the city of Montepulciano where mediaeval architecture and vineyards line the landscape.


Day 1
Arrival in Siena, where you settle in at your centrally located hotel, just a few minutes away from the famous ‘Piazza del Campo’. In the evening you can take a nice stroll into town to have dinner in one of the many nice restaurants, or sip a drink in the ‘Piazza del Campo’.
Hotel *** – Siena
Total walking time: around 5 h. + sightseeing time

Optional Extra day: Siena
Take your time to explore Siena, one of Italy’s most beautiful medieval cities. Its heart is the perfect, shell-shaped Piazza del Campo, scene of the Palio, where you find the Palazzo Pubblico, with its pictures and frescoes including Lorenzetti’s ‘Allegory of Good and Bad Government’. There is also the medieval black-and-white marble Duomo, built in 1196-1216, with the remarkable Libreria Piccolomini, decorated by Pinturicchio. You could also see the Museo dell’Opera with Duccio’s Maestà, the list goes on and on.
Hotel *** – Siena

Day 2
Today you first make a short train journey to Asciano, a beautiful, yet relatively unknown walled town. From here you start your walk in a southern direction. You cross the fascinating hilly region known as the Crete Senesi, a fascinating area of odd-shaped clay hills. In the afternoon you reach the monastery of Monte Oliveto Maggiore, built in the 14th century by the Olivetan monks. Surrounded by a forest of cypresses, this building is famous throughout the world for the frescoes in the courtyard painted by the 15th-century painters Signorelli and Sodoma. The library and church of the convent are architectural masterpieces too. The walk is relatively short so there is time to visit both the charming village of Asciano and the monastery itself. Then you walk the last short stretch and settle in a nearby charming hotel. In the evening you dine at the restaurant on the premises of the hotel.
Hotel *** – Asciano
Distance: 12 km. Approx. 3 h. walking. Ascent & descent: + 100 m./- 25 m.

Day 3
Past the monastery of Monte Oliveto you first walk uphill to the small village of Chiusure, in a commanding position on a ridge, with a wonderful view of the monastery and the whole ‘Crete Senesi’ area. Then you continue your walk, mostly downhill, to Buonconvento, another walled medieval town. Crossing olive tree fields along woodland tracks and so-called ‘strade bianche’ (‘white’ gravel roads), you will eventually reach this small town, where Emperor Henry VII died in 1313. From here you have the possibility of either continuing the walk or taking the bus to San Quirico (or Montepulciano – in case you opt for the 8-day tour), where you stay for the next two nights.
Hotel *** – San Quirico
Distance: 12 km. Approx. walking time: 3-4 h. Ascent & descent: + 25 m./- 150 m.

Day 4
You first make an easy stroll along another ‘strada bianca’ to the wonderful Ripa d’Orcia, a small fortified village in a strategic position above the River Orcia. On the other side of the river lies the castle of Rocca d’Orcia and Monte Amiata, a former volcano, symbol of southern Tuscany and important today for its thermal water. You then walk along the banks of the Orcia and reach Bagno Vignoni, which was built in the 13th century to allow Lorenzo de’ Medici and various popes to relax in healthy thermal water. This little village is very peculiar. Indeed, instead of the usual central square, there is a large thermal pool! Especially on cooler days, the effect of the rising steam is incredible. Then you can either take a bus back to San Quirico or walk up the gravel road and past the hamlet of Vignoni to return to San Quirico.
Hotel *** – San Quirico
Distance: 8 km. Approx. 2,5 h. walking. Ascent & descent: + 75 m./- 50 m.

Optional Extra day: Roundwalk Montalcino – Sant’Antimo
This walk starts from Montalcino, the highest and one of the most scenic villages of the area. It takes you partly through the vineyards, and partly through the more forested landscape south of Montalcino. The goal of the walk is to reach the stunning Abbey of Sant’Antimo (Abbazia di Sant’Antimo), “one of the finest Romanesque religious buildings in Italy.” The church dates from the 12th century and is built in a picture-perfect setting, in a large valley with views of the hill town Castelnuovo dell’Abate, rolling hills covered in olive groves and vineyards, and wild forests.
Hotel *** – San Quirico
Distance: 12,5 km. Approx. 3,5-4 h. walking. Ascent & descent: + 150 m./- 350 m.

Day 5
Today you walk from San Quirico to Pienza, a small, perfectly laid-out Renaissance town. You leave San Quirico in an eastern direction through the medieval town gate. The route mainly follows so-called strade bianche through the archetypal Tuscan landscape. Around lunchtime you reach the wonderful Renaissance town of Pienza, where you have time to look around and perhaps visit the beautiful museum, inside the Palace of Pope Pius II. Pienza is often described as the “ideal city” or the “utopian city”. It is certainly one of the best planned Renaissance towns, where a model of ideal living and government was attempted. It represented the utopia of the “civitas“, based on the concept of a town able to satisfy the needs of a peaceful and hardworking population. Pienza’s location in the centre of the Val d’Orcia, a wonderfully harmonious valley, helps the town to embody the fundamental principle that humanistic architecture attempted to create: a balanced relationship between Man and Nature. After your visit you take the local bus to Montepulciano, where you settle in at a nice welcoming hotel, just below the main square.
Hotel *** – Montepulciano
Distance: 8 km. Approx. 2,5 h. walking. Ascent & descent: + 75 m./- 50 m.

Day 6
After breakfast you walk down the medieval alleys of Montepulciano to the impressive Chiesa di San Biagio, a 16th-Century church nestled on the edge of the village walls, overlooking the winding valley below. From here you commence the walk into the picturesque valley and through vineyards and olive groves, past pastel-coloured villas and across rolling hills. This is a morning of delightful Tuscan scenery, enjoyed and experienced at its best – on foot. You then reach the peaceful village of Montichiello, where you can enjoy a flavoursome lunch under the welcome shade of creeping grapevines with a stunning view out over Montichiello’s ancient village gateway. After lunch you can either continue the walk to the wonderful Renaissance town of Pienza, or join the locals on a short local bus ride back to Montepulciano and enjoy a sightseeing tour of its labyrinthine maze of alleyways and imposing defensive walls. The rest of the afternoon you are free to explore and perhaps shop among Montepulciano’s classy boutiques.
Hotel *** – Montepulciano
Distance: 14 km. Approx. 4-5 h. walking. Ascent & descent: + 250 m./- 350 m.

Day 7
End of the tour. From Montepulciano it’s easy to return to either Rome or Florence.

Tour details


All nights are spent in beautiful, characteristic family-run hotels (generally 3-star; 4/5-star on request) and beautiful agriturismos. All rooms have en-suite facilities. You’ll spend one night in the monastery of Monte Oliveto with good, though spartan rooms, in a unique setting.

Most accommodations are on a B&B basis. Only on the night in Monte Oliveto are you on a half-board basis; the other nights you will be free to make your own dinner arrangements. You can either eat at the premises of the hotel (on some occasions) or choose from the wide choice of restaurants in the area. Your accommodation holder can give you good tips.

No picnic lunches are included in the tour price, but these can be prepared for you by the accommodation holders, or materials for picnics can be purchased in the villages where you’ll be staying. On some occasions you have the option of having your lunch in a restaurant along the way.


It is possible to upgrade this tour, staying in more luxurious 4-star hotels. Accommodation in Pienza is also available, to substitute for the days in Montepulciano. Details and Prices on request.


Moderately easy (2-3): Mostly easy walks, but with nonetheless some walking uphill, sometimes on paths with rough surfaces. On some days extensions or shortcuts are possible.

Fitness: High standard of fitness is not necessary but clients should be able to walk for up to 5 hours a day in hot sun on dusty or stony tracks.

N.B. During Summer, due to the heat, the level of difficulty of this tour definitely increases. We do therefore not recommend to book this tour from about 14th July until 20th August.


Footpaths: Most paths are relatively well maintained; on many occasions you’ll follow so-called strade bianche (un-surfaced roads), easy to follow and very unlikely to get overgrown (we continuously check our routes – please help us by providing you feedback on the quality of the paths).

Waymarking: A large part of the route is waymarked , but on some occasions we have found more interesting routes than those actually waymarked; therefore it is necessary to follow the route descriptions provided together with the maps. With these it is always possible to find your route


  • 1 night in Siena *** – BB
  • 1 night in Monte Oliveto – HB
  • 2 nights in San Quirico d’Orcia *** – BB
  • 2 nights in Montepulciano *** – BB
  • Extensive route notes, with description of the route & tourist information
  • Maps at 1 : 25.000 scale
  • GPS tracks for each day
  • 24/7 assistance
  • Luggage transport
  • Private transfers as specified


  • Departure taxes
  • Visas
  • Travel Insurance
  • Tourist tax
  • Drinks and meals not mentioned in the itinerary
  • Optional additional tours or activities
  • Tips
  • Items of personal nature



Arrival: The tour starts in SIENA, connected with FLORENCE by a frequent bus service.

A taxi pick-up service can be arranged either from Florence (hotel, airport or train station), or from Pisa (airport).

Departure: The tour ends in MONTEPULCIANO. A frequent bus service can bring you to one of the nearest train stations (Montepulciano and Chiusi), from where there are regular trains to both Rome and Florence. Upon request a taxi service is available to bring you directly to your next destination.

Dates & Prices
Please contact us for the latest prices

GuaranteedYou can book this tour with a minimum of 1 person.
LimitedThere are a very limited number of available places on these dates. Immediate booking is recommended.
On RequestAvailability and prices on request.
  • Prices are per person and based on the season within which the first night of the tour falls.
  • Prices are based on 2 people sharing double or twin accommodation. Single rooms (double rooms – single) are available on most trips however the supplements listed apply.
  • If you are travelling alone then on some trips (which include taxi transfers) a ‘Solo Traveller Supplement’ will be applied instead of the normal single supplement.
  • Prices are expressed in Euro’s. There will never be a currency surcharge.
  • Actual exchange rates: GB £ - US $ - CAN $ - CHF - DKK - SEK - NOK - Other currencies.

Tour variations

It is possible to include some extra nights in your tour, in any of the accommodations ‘en route’. For those who have never been in Siena an extra day here is strongly recommended.

At the beginning or the end of the tour there is the opportunity to visit Florence. The tour can easily be extended with a few days there. Also in ROME several good accommodations are available. Details and prices on request.

The tour can also be extended with a few days on a beautiful agriturismo, for some relax in the countryside. Several superb accommodations are available. Details & prices on request.


A luxury version of this tour is also available, with stays in the most authentic luxury hotels of the area. We can offer you a large selection of ‘Premiere Inns’, very good hotels, some among the world’s best hotels, as acclaimed from Condé Nast Traveler, Travel+Leisure and many others.

Genius Loci Travel, as the leading adventure travel company in Italy, can book your room in any hotel you could dream of!


A longer, 10-day version of this tour, which includes both the area North, as well the area South of Siena, is also available.

Also other shorter versions of this tour are available upon request. These tours feature either the area of San Gimignano & Siena, or the Val d’Orcia. See also our other Tuscany tours !


Possible extensions: Rome, Florence, and why not: Umbria ! Prices on request.



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Trip name
Walking the Val d’Orcia – from Siena to Montepulciano
Tour type
Independent Tour
7 days - Bases in charming hotels & agriturismo’s Starting from: € 715,00
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