The essence of Tuscany: Via Francigena & Val d’Orcia

The essence of Tuscany: Via Francigena & Val d’Orcia

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 historic towns of San Gimignano, Colle Val D’Elsa Siena and Montepulciano, and of course all the beautiful medieval villages long the Via Francigena and in the Val d’Orcia: Monteriggioni, already admired by Dante, San Quirico, Buonconvento, Bagno Vignoni and Pienza, arguably the most perfect Renaissance town of Tuscany, as 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 mainly through forests and vineyards, then 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.

Holiday TypeSelf guided walking
Start/FinishColle Val d’Elsa
Duration8 days 7 nights. 6 days walking
SeasonMarch to November


What we do

We put together the trip for you: reserve the hotels, transfer the luggage and organise your transfers to the start of your itineraries. Each tour includes a complete Road book with detailed itineraries, information for visits along the way, a detailed map and total peace of mind with our 24-hour local support.

We work with local operators through-out each destination that are passionate about their regions.

We can tailor make this tour, if you want to add an extra rest day, spend a few days relaxing before or after the trip just let us know and we will be happy to provide a quotation.

Day 1
Arrival in Florence and transfer to Colle Val d’Elsa (either by private taxi or public transport), where you settle in your hotel in the old town, known for its perfectly preserved “tunnel” streets and for its crystal ware. According to your arrival time, you can go for a short visit to the town centre.
Total walking time: around 1 hour + sightseeing time

Day 2
The first day walk takes you at first through the whole historical town centre of Colle Val D’Elsa, perhaps not as famous as other Tuscan towns, but with a very interesting centre. Then you descend into the valley where you pick up one of the supposed routes of the ancient Via Francigena. Along this route, through a pleasant hilly landscape of vineyards and forests you reach the small hamlet of Bibbiano. Another descent brings you down into the valley of the river Foci. Follows a short stretch through the river valley and past an old water mill. Then you start to climb up along a comfortable track up to the beautiful agriturismo, where you will spend the next two nights. Be sure to be there on time, to enjoy its fabulous setting and surroundings, and perhaps its library or swimming pool. For those who want there is also a longer option to walk to here. Dinner at the private restaurant is included tonight.
Total walking time: around 3,5 hours + sightseeing time (4-5 hours with extra option).

Day 3
After breakfast you begin your walk to San Gimignano, directly from the agriturismo. First make your way up along the ridge to the small hamlets of Ciuciano and San Donato, passing along several old ‘pievi’ (countryside churches) and villa’s and often with wonderful views of the skyline of San Gimignano. This town – sometimes referred to as having the only “skyscrapers” in Tuscany – is an absolute must, a wonderful medieval city with picturesque vineyards, olive and cypress groves on either side. You have time to explore this small romantic old town with towers that remain from medieval times. The town once had 52 of these towers (there are now less than a dozen). Wealthy, prominent families would use the height of these towers to distinguish themselves, and the towers also served to alert the inhabitants of this walled town of approaching friends and foes. Do make a nice stroll along its impressive medieval town walls. In the town itself there are numerous places to enjoy lunch. Then you follow the Via Francigena back to your agriturismo: first to the convent of Monte Oliveto, located on a wide ridge, then down to a small stream, which you have to cross, before you climb back up to your agriturismo. At night you have another good meal at the agriturismo.
Total walking time: around 4 – 5 hours (+ circa 1 h. in San Gimignano – various options).

Day 4
Today you leave the agriturismo, heading for Monteriggioni, defined by Dante as a crown in the landscape. The walk first brings you down into the river valley, and then more or less following the Foci, you reach one of the most wonderful Romanesque churches of Tuscany, la Badia a Conèo. The next stop is Quartaia, followed by Gracciano, once one of the most important wheat towns of Tuscany. Another short stretch brings you to the Badia ad Isola, once an important stop on the medieval Via Francigena, and a very intriguing building. The final destination for today is Monteriggioni, where you’ll have the time for a drink in the square. Then you are picked up by your taxi and transferred to 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 5
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 6
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 Montepulciano, where you stay the last two nights.
Total walking time: around 3,5 hours + sightseeing time (shorter option: 1,5 – 2,5 hours).

Day 7
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 can either continue the walk and reach the wonderful Renaissance town of Pienza, or 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 3,5 hours + sightseeing time (5,5 hours with extra option).

Day 8
End of the tour. From Montepulciano it’s easy to return to either Rome or Florence.

Trip season Tour price Single supplementSolo traveller supplement
15 March – 14 April 2019 € 910 € 175 € 275
15 April – 30 September 2019 € 930 € 175 € 275
01 October – 15 November 2019€ 910 € 175 € 275


  • 1 night Hotel in Colle Val d’Elsa*** – BB
  • 2 nights Agriturismo in San Gimignano*** – HB
  • 1 night in Siena*** – BB
  • 1 night in Monte Oliveto – HB
  • 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

Your Accommodation


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 Colle Val d’Elsa. Here you stay in a comfortable 3-star hotel in the old town centre, centrally located at walking distance from the bus station, all the main monuments of the medieval town centre and close to many nice restaurants.

Nights 2 & 3: These are spent at one of the nicest agriturismo’s of Tuscany, a beautifully restored old fortress along the Via Francigena. The evening dinners are prepared by one of the best Tuscan chefs, who is also a painter.

Night 4: This night is spent in a good hotel in the historic heart of Siena.

Night 5: 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 6 & 7: The last nights are spent in 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.


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 San Quirico or Pienza is also available, to substitute for the days in Montepulciano.

Where you rest your head after an active day is hugely important to us. We go to great lengths to find properties that are unique expressions of the region you are travelling through. Think of them as the charming and intimate garnish atop your trip. 

Whether nestled in the heart of a village or lost in the countryside and surrounded by nature, all accommodations are chosen using a strict criteria of comforthospitality, and authentic charm. We like to use locally run independent small hotels, guest houses and B&Bs instead of the larger “chain” hotels.  All of them are hand-picked, visited, and re-visited by our local partners. On most of our holidays you will be staying in different hotels and their  uniqueness and individual character only adds to the enjoyment of your holiday. You will also benifit with knowledge that your trip is contributing to local economies, and supporting local family run businesses.

You will be welcomed in a double or twin room (2 beds) – based on double occupancy.
All of our rooms have private bathrooms.
Individual rooms are possible upon request when you book; they are subject to availability and incur a supplemental fee.
For biking trips, all of our inns have a safe place to keep bicycles for the night

Flights are not included in the price. Adventure Holidays do not book flights. We will  advise you on best times, dates and airfares to book.


Arrival: The tour starts in COLLE VAL D’ELSA, connected with FLORENCE & PISA by frequent public transport.

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 8 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.

From Price pp


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