Tuscany and
the Best of the
Via Francigena

From San Miniato to Buonconvento
along the Pilgrims Path

The heart of the Via Francigena. Your trip starts in San Miniato, one of the hidden gems of the route and continues along an itinerary of extraordinary beauty; from the thousand-year-old Pieve di Chianni, where Sigerico himself slept, to the crenellated towers of the Monteriggioni Castle. Walk the legendary dirt roads of Siena, among dreamy views and fortified villages where time seems to have frozen. Finally, upon reaching Buonconvento you’ll discover why it’s called ‘happy fortunate place’. 

We offer this as an 9 day self guided walking tour
or a shorter 5 day trip from San Gimignano to Siena.

Key information

April to October

Self Guided

Duration: 5 or 9 days

Grading: Moderate

Nearest Airport: Pisa (PSA), Florence (FLR), Bologna (BLQ)
or Milano (MXP or LIN)

Starting point: San Miniato

Dog friendly 

At A Glance

Days 1 - 2

Your trip starts from San Miniato, a jewel of the Via Francigena. The Seminary, (from which the main square takes its name), will surprise you with its façade: don’t miss it illuminated! Perhaps after having enjoyed a risotto powdered with the typical white truffle, a local gastronomic pride.

A demanding leg, but one with unique beautiful scenery, awaits you. From San Miniato you walk along an asphalted section of road, before passing through the glorious crests of the hills of the Val d’Elsa: along the road you can cross the threshold of the Pieve di Chianni, following in the footsteps of entire generations of pilgrims.  


Days 3 - 4

This leg of the journey is short but rich in splendid natural scenery. Leading to San Gimignano – one of the most beautiful towns along the Via Francigena, you will get a taste of your arrival when you see the famous towers that make its skyline unmistakeable. Do not miss the view of the medieval town and its surrounding valleys from the top of the Torre Grossa, and if you have enough energy, venture up the steps of the Rocca di Montestaffoli, for an even more special view. During the evening you can take a quiet stroll to admire the illuminated town.

From San Gimignano you will continue, up and down, through the Tuscan hills. At one point of the journey (not yet well marked) you will come to Molino d’Aiano, one of the halting places along the ancient route of Sigerico. Today’s destination is Colle Val d’Elsa, a Tuscan village which will take you back in time, with its charming old town centre and narrow alleyways winding through the stone walls.


Days 5 - 6

Prepare yourselves for one of the most beautiful sections of the Via Francigena: a meditative route, where you can admire the Pieve di Strove (from the outside) and stand in the quietness of the splendid Abbadia at Isola, another stage in the journey of the Archbishop Sigerico, where time stopped 1000 years ago as he passed through. Your breath will be taken away when you see the castle of Monteriggioni, with its crown of towers, built on a hill as a defence against the ancient republic of Siena. Within it, a small ancient world, with the beautiful square and small gardens – gather your breath, before climbing up onto the walls to admire the surrounding view.

From Monteriggioni you will start your walk again along the white roads of the Sienese countryside, passing though the old, uninhabited medieval village of Cerbaia. Experience the same feelings as the ancient pilgrims when you pass through porta Camollia, the traditional Francigena entrance to the town of Siena. For an unforgettable way to celebrate, order a plate of pici all’aglione in the illuminated Piazza del Campo. And don’t forget the panforte!



Days 7 - 9

The Crests of the Val d’Arbia offer unforgettable views. After saying goodbye to Siena, resting on the hills on the horizon, you will travel along the typical dirt roads of Siena as far as the fortified village of Lucignano, with its fine Church. At the gates of Monteroni d’Arbia you will be able to admire the impressive Grancia di Cuna, a fortified farm which stored the wheat reserves destined for the republic of Siena.

From Lucignano you will continue your journey through the Valle dell’Ombrone to Buonconvento. Crossing the gate of the walls and entering the old town centre of the village, you will discover why its name means “happy fortunate place”. Walk through the picturesque streets, where life is lived quietly following the slow rhythms of a provincial village. Art lovers will be able to admire the works of some of the most famous Sienese painters in the Museum of Sacred Art of the Val d’Arbia.

Read about the Aostan section of the Via Francigena here.

   Take a look


Need To Know


All accommodation is carefully selected based on the location, atmosphere and/or unique services. 

We choose comfortable 3* hotels, farmhouses (agriturismo) and B&Bs where all rooms have private en-suite bathrooms. If a hotel is fully booked, then we will book a similar one for you and inform you about the change.

Extra stays: You can book additional night(s) at any of the accommodation along the way.

What’s included


  • All accommodation
  • All breakfasts
  • Packed lunches
  • Optional half board on request
  • Luggage transfers
  • 1:50 000 map, GPS coordinates and information guide

Throughout the trip there are plenty opportunities to taste both the greeat local food and a wide array of prestigious wines of the region.



This is a SELF GUIDED trip, however should you prefer to have the expertise of an International Mountain Leader then please don’t hesitate to get in touch.

We adopt an excellent guiding ratio meaning we can cater for differing levels within the group:

One Guide: 1 – 7 clients

Two Guides: 8 – 14 clients


Booking and Price

9 days and 8 nights 


 1/4/2024 – 23/4/2024  4/10/2024 – 31/10/2024 

Single Room €1398

Double / Twin  Room €873 pp

Triple Room €782 pp


24/4/2024 – 26/5/2024   

Single Room €1462 

Double / Twin Room €908 pp

Triple Room  €805 pp 


27/5/2024 – 12/6/2024.  1/7/2024 – 12/7/2024   20/9/2024 – 3/10/2024 

Single Room €1504 

Double / Twin Room €924 pp

Triple Rooms €820 pp  


13/6/2024 – 30/6/2024  13/7/202 – 25/7/2024.  23/8/2024 – 19/9/2024 

Single Room €1529

Double / Twin Room €935 pp

Triple Room €828 pp  


26/7/2024 – 22/8/2024

Single Room €1643

Double / Twin Room €1012 pp

Triple Room €877 pp 


5 days and 4 nights  


1/4/2024 – 27/7/2024  26/8/2024 – 31/10/2024

Single Room €735

Double / Twin  Room €443 pp

Triple Room €430 pp 


28/7/2024 – 25/8/2024   

Single Room €844 

Double / Twin Room €513 pp

Triple Room €430 pp


We manage every booking independently to ensure attention to detail and provide a personalised service.

* Dog friendly €11 per day


Book Now              Enquire  

Trip Highlights

• Stroll around the historic centre of San Miniato
• Admire the iconic skyline of San Gimignano from the Val d’Elsa
• Stand in silence in the Pieve di Chianni, at Gambassi terme
• Walk along the covered street in the centre of Colle Val d’Elsa
• Walk the walls of Monteriggioni, as mentioned in Dante’s Divine Comedy

Nature, Culture, History and Spirituality

Not just an adventure, but an act of devotion.