Tuscany - Along the Via Francigena from San Gimignano to Siena - TUS 2

Tuscany - Along the Via Francigena from San Gimignano to Siena
Comfort level
5 Days - Bases in charming hotels & agriturismo’s
Starting from: € 520


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 all the beautiful medieval villages and historic towns along Italy’s most famous medieval pilgrim’s road, the Via Francigena: Monteriggioni, already admired by Dante, San Gimignano, Colle Val d’Elsa and of course Siena, arguably the most perfectly preserved medieval 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, poppies in Spring and the wild cyclamen in autumn. Most of all, many of the views have changed little for hundreds of years.  The area North of Siena is an amazing landscape of rolling hills, alternating vineyards and forests, while cypresses line the way leading to the distant farmhouses. Walking here is an unforgettable experience!

You spend a night in beautiful Colle Val d’Elsa, a few nights in one of the best agriturismo’s of Tuscany, and the last night in the heart of Siena, in one of the most characteristic small hotels.



Day 1
Arrival in Florence and transfer to Colle Val d’Elsa (either by private taxi or public transport), where you settle in at your hotel just below the medieval town centre, known for its perfectly preserved ‘tunnel’ streets and its crystalware. Depending on your arrival time, you could go for a quick visit to the town centre.
Hotel *** – Colle Val d’Elsa
Approx. walking time: 1 h. + sightseeing time

Day 2
The first day walk initially takes you all the way round the historical town of Colle Val D’Elsa, perhaps not as famous as other Tuscan towns, but with a very interesting town 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, which you follow for a short stretch. Then you start to climb up on a comfortable track to the beautiful agriturismo where you will spend the next two nights. Make sure you’re there on time to enjoy its fabulous setting and surroundings, and perhaps its library and swimming pool too. For those who feel like it there is also a longer walking option to get here. Dinner at the private restaurant is included tonight.
Agriturismo *** – San Gimignano
Distance: 14 km. Approx. 4 h. walking. Ascent & descent: + 125 m./- 100 m.

Day 3
After breakfast you begin your walk to San Gimignano, straight from the agriturismo. First you make your way up along the ridge to the hamlets of Ciuciano and San Donato, going past several old ‘pievi’ (countryside churches) and villas and often with wonderful views of the San Gimignano skyline. This wonderful medieval town – sometimes referred to as having the only “skyscrapers” in Tuscany – is an absolute must, with picturesque vineyards and olive and cypress groves on either side. You have some time to explore this little romantic town with its medieval towers, of which there were once 52 (there are now less than a dozen) – wealthy, prominent families would use the height of these towers to distinguish themselves, but the towers also had a practical use in alerting the inhabitants of this walled town of approaching friends and foes. Do make a nice stroll around its impressive town walls. 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. In the evening you have another nice meal at the agriturismo.
Agriturismo *** – San Gimignano
Distance: 16 km. Approx. 5 h. walking. Ascent & descent: +/- 250 m.

Day 4
Today you leave the agriturismo and head for Monteriggioni, described as a crown in the landscape by Dante. 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 in Tuscany, la Badia a Conèo. The next stop is Quartaia, followed by Gracciano, once one of the most important wheat towns in 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 time for a drink in the square. Then you are picked up by your taxi and transferred to 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
Distance: 20 km. Approx. 5,5 h. walking. Ascent & descent: +/- 100 m.

Day 5
End of the tour. From Siena there are regular buses back to Florence (and also to Rome).

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.

Only the two nights at the agriturismo are on a half-board (HB) basis, i.e. with dinner included; the other nights you will be free to make your own dinner arrangements. You can then 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 to have your lunch in a restaurant along the way.


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 as an alternative to the hotel 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.

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 Colle Val d’Elsa *** – BB
  • 2 nights in S. Gimignano **** – HB
  • 1 night in Siena *** – 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


The tour starts in COLLE VAL D’ELSA, 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).

The tour ends in SIENA. A frequent bus service can bring you back to Florence. Upon request a taxi service is available to bring you directly to your next destination.

Dates & Prices
5 days prices
  Trip season Tour
On Request 01 November 2021 - 14 March 2022 - - - - - - - - - CONTACT US
Guaranteed 15 March - 05 November 2022 € 520 € 110 € 160
On Request 06 November 2022 - 14 March 2023 - - - - - - - - - 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 longer, 8- or 10-day version of this tour, which includes beautiful walks in Val d’Orcia is also available.

In this tour some of the best parts of the Via Francigena are included. In case you want to walk more stages, several tours – also through this area – are available.

See also our other Tuscany tours !


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Trip name
Tuscany – Along the Via Francigena from San Gimignano to Siena
Tour type
Independent Tour
5 Days - Bases in charming hotels & agriturismo’s Starting from: € 520,00
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End date
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