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: € 650


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 your centrally located hotel, and 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’.
Total walking time: around 5 hours + sightseeing time.

Optional extra day
Take your time to explore Siena, one of Italy’s most beautiful medieval towns. Its heart is the perfect, shell shaped Piazza del Campo, scene of the Palio, its Palazzo Publico with pictures and frescoes including Lorenzetti’s ‘Good and Bad Government’. There is also a cathedral built in 1196-1216 with the remarkable Libreria Piccolomini, decorated by Pinturicchio. See the Medieval Duomo of black and white marble, Museo dell’Opera with Duccio’s Maestà, the list goes on and on….

Day 2
Today you first make a short train ride to Asciano, a beautiful, yet unknown, walled town. From here you start your walk in southern direction. You cross the fascinating area of hills called the Crete Senesi and you reach the Monastery of Monte Oliveto Maggiore, built in the 14th century by the Olivetan monks. Surrounded by a forest of cypresses, this place is world-famous for the frescoes in the courtyard painted by the 15th century painters Signorelli and Sodoma. Even the library and the church of the convent are architectural masterpieces. The walk is relatively short so there is time to visit both the charming village of Asciano and the monastery. You settle in one of the quiet, comfortable rooms. In the evening you dine in the nearby restaurant in the old entrance tower.
Total walking time: around 4,5 hours + sightseeing time (5,5 hours with extra option).

Day 3
From the Convent of Monte Oliveto you first walk uphill to the small village of Chiusure, in a commanding position on a ridge, with a wonderful view on the monastery of Monte Oliveto and the whole area of the ‘Crete Senesi’. 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 the Emperor Henry VII died in 1313. From here you have the possibility to either continue the walk or take the bus to San Quirico, where you stay the next two nights.
Total walking time: around 3,5 hours + sightseeing time (shorter option: 1,5 – 2,5 hours).

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 opposite side there is the castle of Rocca d’Orcia and the Monte Amiata, a former volcano, symbol of southern Tuscany and still important for its thermal water. You then walk along the shores of the Orcia river and then reach Bagno Vignoni, which was built in the 13th century to permit Lorenzo de’ Medici and the popes to relax in healthy thermal water. This small 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 opt to take a bus back to San Quirico, or you walk up the gravel road, and along the hamlet of Vignoni you return to San Quirico.
Total walking time: around 3,5 hours + sightseeing time (5,5 hours with extra option).

Day 5
Today you walk from San Quirico to Pienza, a small, perfectly laid out Renaissance town. Through the medieval town gate you leave San Quirico in Eastern direction. The route follows mainly so-called strade bianche through the archetypical Tuscan landscape. At about lunch time you reach the wonderful Renaissance town of Pienza, where you have time to explore, 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 certainly is one of the best planned of Renaissance towns, where a model of ideal living and government was attempted. It represented the so-called 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 a nice welcoming hotel, just below the main square.
Total walking time: around 3,5 hours + sightseeing time (5,5 hours with extra option).

Day 6
After breakfast you walk down the medieval alleys of Montepulciano to the impressive Chiesa di San Biagio, a 16th Century church nestled at the edge of the village walls, overlooking the winding valley below. From here you commence our walk into the picturesque valley and through vineyards, olive groves, past pastel coloured villas and across rolling hills. This is a morning of delightful Tuscan scenery enjoyed and experienced at its best – by foot. You then reach the restful village of Montichiello, where you can enjoy a flavoursome lunch under the welcome shade of creeping grapevines with a stunning view out upon Montichiello’s ancient main village gateway.
After lunch you continue the walk and reach the wonderful Renaissance town of Pienza from the other side. Join the locals on a short local bus ride back to Montepulciano and then enjoy a sightseeing tour of its labyrinthine maze of alleyways and laneways and imposing defensive walls. The rest of the afternoon is then at leisure to explore and perhaps shop amidst Montepulciano’s classy boutiques.
Total walking time: around 4,5 hours + sightseeing time (2,5 hours to Montichiello only).

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 agriturismo’s. All rooms have en-suite facilities. One night you’ll spend in the monastery of Monte Oliveto, with good, but Spartan rooms, in a unique setting.

Accommodation is generally on B&B basis, in most accommodations. Only in the agriturismo (2 nights) and in the monastery of Monte Oliveto (1 night) you are on half board-basis, the other nights you will be free to organise your dinner. 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 stay. On some occasions you have the option to have your lunch in a restaurant along the way.

Night 1: The first night is spent in a good hotel in the historic heart of Siena.

Night 2: This night is spent in one of the most beautiful convents of Tuscany at the Abbazia Monte Oliveto Maggiore, a typical red brick Monastery where friars of the Benedictine Order still worship. Staying overnight there is a memorable experience. You have dinner in the restaurant located in the old entrance gate of the monastery (in alternative: in case the abbey is not available you will sleep in a beautiful agriturismo nearby).

Nights 3 & 4: These nights are spent in the beautiful small medieval town of San Quirico, either in a beautiful hotel in the town centre, or in a comfortable hotel with pool, overlooking the valley.

Nights 5 & 6: These nights are spent in yet another beautiful small medieval town, Montepulciano. Your hotel is located in the town centre, at only a short distance from all the main monuments and many nice restaurants. N.B. In alternative you could opt for 2 nights in Pienza.


It is possible to upgrade this tour, staying in more luxurious 4-star hotels (except for the agriturismo in San Gimignano – which is already 4-star level). Accommodation in Pienza is also available, to substitute for the days in Montepulciano.


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.


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 nigths in Montepulciano*** – BB
  • Extensive route notes, with description of the route & tourist information
  • Maps at 1 : 25.000 scale
  • 24/24 h local assistance
  • Luggage transport
  • Private transfers as specified



  • Departure taxes
  • Visas
  • Travel Insurance
  • 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 after breakfast on day 10 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
7 days prices
  Trip season Tour
On Request 15 November 2020 - 14 March 2021 - - - - - - - - - CONTACT US
Guaranteed 15 March - 30 April 2021 € 650 € 200 € 275
Guaranteed 01 May - 30 September 2021 € 670 € 200 € 275
Guaranteed 01 October - 14 November 2021 € 650 € 200 € 275
On Request 15 November 2021 - 14 March 2022 - - - - - - - - - CONTACT US

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: € 650,00
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