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 


1/4/2023 – 23/4/2023  1/10/2023 – 31/10/2023 

Single Room €1204

Double / Twin  Room €867 pp

Triple Room €789 pp


24/4/2023 – 24/5/2023    

Single Room €1258 

Double / Twin Room €898 pp

Triple Room  €810 pp

25/5/2023 – 16/6/2023 

Single Room €1306 

Double / Twin Room €919 pp

Triple Rooms €820 pp 


17/6/2023 – 18/7/2023  25/8/2023 – 30/9/2023

Single Room €1344

Double / Twin Room €943 pp

Triple Room €835 pp 


19/7/2023 – 24/8/2023

Single Room €1,369

Double / Twin Room €956 pp

Triple Room €845 pp 



5 days and 4 nights 


1/4/2023 – 27/5/2023  1/10/2023 – 31/10/2023

Single Room €654

Double / Twin  Room €428 pp

Triple Room €382 pp



28/5/2023 – 20/7/2023   21/8/2023 – 30/9/2023

Single Room €704 

Double / Twin Room €451 pp

Triple Room €397 pp



21/7/2023 – 20/8/2023 

Single Room €715

Double / Twin Room €458 pp

Triple Room €400 pp

* Dog friendly €11 per day


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


Book Now              Enquire  

Terms & Conditions

Terms and Conditions (updated November 2020)All trips are sold subject to these Terms and Conditions (hereinafter T&Cs). 

1. Insurance

All clients need to be adequately insured for all activities they are taking part in. Insurance must include repatriation and details should be provided at the beginning of each trip.

All European clients should obtain a European Health insurance card (EHIC), however, this is not a substitute for travel insurance.

2. Health and fitness

Trip members have the responsibility to select a trip appropriate to their abilities and interests. In order to assist with this, all trips are graded and we welcome the opportunity to discuss trip details/answer questions in advance of your reservation. Trip members must be in sufficiently good health to undertake the trip, and if unsure seek medical advice in advance. For your own safety, you need to inform us of any medical conditions in advance or at the start of the trip. Trip members are also required to bring adequate clothing/equipment as advised in the pre-departure information.

3. Dietary Requirements

We endeavor to work with clients and accommodate their dietary requirements. However such is the nature of adventure travel we may be limited to specific menus e.g remote Mountain Huts, Tea Houses in the Himalaya’s etc. We fully encourage you to contact us in advance to discuss your requirements then we have every opportunity to explore options thereafter.

4. Cancellations and Fee Schedule Per Person

91 days or more prior to departure – €250 cancellation fee

61 – 90 days before departure – 25% of the trip cost

46 – 60 days before departure – 50% of the trip cost

45 days or less: 100% of trip cost

Fees are calculated from the date we receive written cancellation notice which can be via email. If clients are unable to access email and cancel over the phone we will confirm in writing the cancellation.

If you cancel 91 days or more prior to departure, it may be possible to transfer to another trip without occurring any fees. Please discuss this with us in the first instance.

With specific departures, there may be an increase in cancellation fee if the accommodation provider T & Cs mean we are liable for payment.

4.1 Cancellation due to COVID travel restrictions.

If your chosen destination country or the country where you reside have restrictions in place due to COVID, meaning you are unable to travel, you have three options:

4.11 Postpone your trip until a later date.

4.12 Take a credit note and use against a future trip with LBH.

4.13 Request a full refund.

If any other reasons prevent you from travelling, including quarantine measures then our normal (4) T&Cs will apply. We recommend that you check with your travel insurance provider to fully understand your level of cover.

5. Complaints

If you have a complaint, please contact us as soon as possible, in the first instance your leader is often your obvious point of contact. This ensures we have every opportunity to explores solutions to the problem(s) arising and we will do all we reasonably can to resolve the complaint. You must tell us within 4 weeks after your holiday of any complaints that you feel have not been dealt with properly.

6. Alterations By Us

We will tell you as soon as reasonably possible if we must make any alteration to your holiday. Most alterations are minor, but very occasionally we might have to make a major alteration. A major alteration is a change of location or to a lower standard of accommodation for a substantial part of your holiday, a change in start/finish dates or necessary price rise in your holiday caused by rises in costs (e.g. exchange rates, internal transport etc). You may then choose as follows:

  • To accept these alterations
  • To withdraw from the holiday, in which case we will repay all monies paid to us including your deposit and this is the sum of our liability to you
  • To accept an alternative holiday that we may propose to you, in which case if the proposed holiday is a lower price we will pay you the difference and if it is a higher price we may ask for the difference.

You must inform us of your choice as soon as possible after we contact you.

7. Group Leadership

On a guided holiday your leader is responsible for the safety and enjoyment of the whole group and has sole discretion, on behalf of Live Breathe Hike, to exclude temporarily a participant from the group. They may also choose to terminate the participants holiday without the possibility of a refund if the leader thinks the participant is likely to endanger the group safety or spoil its enjoyment.

8. Your Responsibility

Mountain holidays by their very nature are adventurous, with a certain level of risk is undertaken. Individuals need to conduct themselves in a safe and responsible manner at all times; responding to advice, guidance, and instruction that may be given by the group leader / experienced professional and take all reasonable actions to eliminate accidents or injury.

9. Our Responsibilities

We will take all reasonable care to ensure that the information we give to you is accurate, including on our website, in your schedule and information pack. We will do all that we can to provide the service as described in the information we give to you. We are not liable if any failure is:

  • Attributable to anyone other than us
  • Attributable to a third party unconnected to us, and unforeseeable or unavoidable
  • Due to unusual and unforeseeable circumstances beyond our control and could not have been avoided even if all due care had been taken
  • Due to an event which even with all due care we could not foresee or forestall

10. Cancellation By Us

Live Breathe Hike reserves the right to cancel any trip prior to departure for any reason whatsoever, including insufficient signup or logistics problems that may impede trip operations. The refund of all land payments received shall relate Live Breathe Hike from any further liability.

Live Breathe Hike must normally make substantial payments to its suppliers far in advance of the scheduled trip departure date. If a trip is canceled due to force majeure; (acts of God, war, strikes, earthquake, flooding etc), Live Breathe Hike will promptly refund the portion of the trip cost not already advanced to suppliers and use its best efforts to recover and refund the balance as promptly as possible. However, Live Breathe Hike does not guarantee recovery of any or all of the advance payments made.

11. Additional Costs

Live Breathe Hike shall not be liable for (a) expenses such as additional nights and meals not specified in the individual trip itineraries, but which may required to get to from a trip start or end; expenses due to the delay of a trip for any reason (e.g. bad weather, trails conditions, land slides, flooding, sickness etc); (c) expenses occurred in recovering lost luggage by airlines, belongings left behind on a trip or in shipping purchases or other goods home from abroad; (d) visa and other incidental costs.

Live Breathe Hike reserves the right to take photographic or film records of any trips, and may use any such records for promotional and/or commercial purposes without payment.


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.