Weekend on Tuscan Via Francigena from San Gimignano to Siena

LEVEL
2
DISTANCE
48 km
DURATION
4 days | 3 nights
PERIOD
Apr May Jun Jul Aug Sep Oct
PRICE FROM
€ 400
CO2e FOOTPRINT
45 Kg/person
  1. Italy
  2.  | 
  3. Self-Guided
  4.  | 
  5. Tourcode ITSM362

A long weekend walking the Via Francigena from San Gimignano to Siena, through the rolling hills of Tuscany. This short self-guided tour is designed for those who want to experience one of Italy’s most iconic routes at a relaxed pace, without giving up comfort.

Starting in San Gimignano, a UNESCO World Heritage Site you will follow well-marked trails across vineyards, olive groves and quiet countryside to Colle di Val d’Elsa, known for its historic centre and crystal production. Just below the town, the Parco Fluviale dell’Elsa offers a refreshing break with clear waters, lush vegetation and shaded paths. Continue to Monteriggioni, a perfectly preserved walled village and one of the highlights of the Via Francigena, before reaching Siena, where you can explore Piazza del Campo and its remarkable Gothic architecture.

Each day combines manageable walking distances with rewarding scenery, making this itinerary ideal even for those approaching their first walking holiday. Along the way, you will also enjoy the region’s food and wine traditions, with plenty of opportunities to taste local specialties and experience authentic Tuscan hospitality. This short walking holiday is an ideal introduction to the Via Francigena.

Highlights

  • San Gimignano and its medieval skyline characterised by towers and history, before stepping straight into the countryside.
  • The Elsa River Park, a surprising stretch of water and greenery along the route: clear streams, small waterfalls and shaded paths that offer a refreshing break from the classic Tuscan hills.
  • Walk into Monteriggioni, the walled village, as pilgrims did centuries ago, crossing its perfectly preserved walls and enjoying one of the most atmospheric stops along the Via Francigena.
  • Siena, the perfect finale: exploring its historic centre, from Piazza del Campo to the Duomo—an ideal reward after days on the trail.
     
     
     

Itinerary

Day 1

San Gimignano

San Gimignano

San Gimignano is a small medieval gem set among hills and vineyards, famous for its unmistakable skyline of towers rising above the landscape. We recommend getting lost in its cobbled streets, discovering corners rich in history, before climbing one of its towers to enjoy sweeping views over the Tuscan countryside. Take a break in Piazza della Cisterna to try an artisanal gelato—said to be among the best in the world—then continue to the Duomo, with its remarkable frescoes. In the evening, when the crowds fade and the light softens, the village regains its most authentic atmosphere, perfect for a relaxed dinner in a local trattoria.

Day 2

From San Gimignano to Colle Val d'Elsa, 12 km

From San Gimignano to Colle Val d'Elsa, 12 km

From San Gimignano, you will walk up and down through the gentle Tuscan hills. Along the way, at a point that is not always clearly marked, you will reach Sce Martin in Fosse, one of the ancient stopping places along Sigeric’s route. Today’s destination is Colle di Val d’Elsa, a charming Tuscan town that feels frozen in time, with its historic centre and narrow streets winding between old stone walls.

Distance: 12 km

Elevation gain: +287/-222 m

Day 3

From Colle Val d'Elsa to Monteriggioni, 16 km

From Colle Val d'Elsa to Monteriggioni, 16 km

Get ready for one of the most beautiful sections of the Via Francigena: a peaceful, almost meditative walk. Along the way, you can admire the Pieve di Strove (from the outside) and stop at the quiet Abbey of Abbadia a Isola, another historic halt on Sigeric’s journey, where time seems to have stood still for over a thousand years.

The highlight comes with the first view of Monteriggioni, its iconic ring of towers rising above the hill, once built to defend the Republic of Siena. Inside, a small medieval world awaits, with a charming square and quiet corners to rest before walking along the walls and enjoying the surrounding views.

Distance: 16 km

Elevation gain: +287/-222 m

Day 4

From Monteriggioni to Siena, 20 km

From Monteriggioni to Siena, 20 km

From Monteriggioni, continue along the classic white roads of the Sienese countryside, passing through the abandoned medieval hamlet of Cerbaia. As you approach Siena, you will experience one of the most symbolic moments of the journey: entering the city through Porta Camollia, the traditional gateway for pilgrims on the Via Francigena.

To celebrate your arrival, head to the illuminated Piazza del Campo and enjoy a plate of pici all’aglione. And of course, don’t forget to try panforte, Siena’s traditional dessert.

Distance: 20 km

Elevation gain: +300/-250 m

Details

Included


What is included

  • 3 Nights in double room in **/*** hotels , B&B and agriturismi with breakfast
  • 1 dinner in Monteriggioni
  • Official guide of the route, App
  • Pilgrim Passport
  • Medical and luggage travel insurance
  • 24h phone assistance

What is not included 

  • Transfers to the starting location and from the arriving location of the tour
  • Luggage transfer from hotel to hotel
  • Lunches and dinners, if not otherwise stated
  • Visits and entrance fees - tips
  • Personal expense
  • Everything that is not mentioned in the "What is included" section.

Optional Services

These services can be added to the ones included in the base price of the tour:

  • Single room supplement
  • Luggage transfer from hotel to hotel (1 item per person, max 20 kilos, size 65x40x30 cm)
  • Extra nights
  • Cancellation insurance
  • Transfers to reach the starting location or to leave the arriving location of the tour, which will be quoted on request.

Classic Hotels


For our trips, we always choose accommodation with private rooms and private bathrooms. In rare cases, shared accommodations or shared bathrooms may be provided, so we recommend carefully checking the inclusions section to understand the type of accommodation included in the trip you are interested in.  

We place great importance on the choice of accommodations and select hotels with care and attention. We understand how essential it is to rest well after a day of walking. We always prefer cozy and characteristic establishments, preferably family-run, that fully embody the spirit of the place and offer hospitality with courtesy and comfort.  

Where, due to the nature of the route, accommodation options are limited, we choose the one that best aligns with our standards.

When to travel


The climate in Tuscany is generally very mild with differences depending on the geography  of the  region, from coasts and valleys to the continental areas.

The warmest months are generally July and August, with temperatures ranging from 23°C up to 30°C; the valleys can often see higher  temperatures and 38°C to 40°C is not uncommon.

While June and September offer both nice warm weather. Of course, there are always exceptions or dry spells that cause a few days to get really hot.Spring (April and May) and Autumn (October and November) are dry, with sunny days but the chances of rain are high.The weather can change very quickly and you must be prepared forrain, mist, wind, fog (and even hail or snow at higher elevations) –especially in spring and autumn. 
 

Is this for me?


This trip is ideal if you want to discover one of the most beautiful sections of the Via Francigena but only have a few days available. It’s also an excellent option if you’d like to test your fitness level before taking on a longer journey.

With balanced stages and well-marked trails, it’s suitable both for first-time walkers and for more experienced travellers looking for a short getaway. If you enjoy combining nature, historic villages and good food at the end of the day, this trip is for you.

What to bring


Clothing and other items
You will need your regular walking/cycling gear, including some sort of reflective garment. For the evenings, smart outdoor style trousers (or shorts) are invaluable, as are quick-dry t-shirts. These can be washed easily and will dry overnight and still look good for sightseeing or having a drink in town.

Take as little as possible to avoid potentially lugging a heavy suitcase up three flights of stairs at the end of the day. Please be aware that laundromats (“Laverie”) are not common in rural areas, so plan to do handwashing of small items.

Lightweight walking shoes/ trainers
For wearing around towns & villages. They can also be a back-up pair.

Socks & underwear
Take only good quality socks with quick-dry and insulating qualities. Road test them before you go on the trip. Take a suitable quantity of underwear as washing facilities are limited.

Warm jacket, hat, gloves
Bring a fleece, Polartec or warm layers for the evenings especially in spring or autumn; be sure it is totally suitable for your needs.
A fleece jacket which blocks the wind (Wind-stopper) is the most preferable. In the summer months a lightweight jacket is suitable for evenings.
If you are cycling/walking in mountainous or coastal areas, even in the height of summer, the weather can change very quickly and unexpectedly and you should be prepared for fog, mist, rain, snow or hail at any time. Always take an extra layer with you, as well as a warm hat and gloves.

Waterproof jacket & trousers
If you are caught in heavy rain, with good waterproof clothing you should remain dry. Remember that most garments will lose their properties over time. Few will remain waterproof for more than five years and many deteriorate in three years or less. We recommend a rain jacket with a good hood and collar and waterproof or thermal walking/cycling trousers or tights.

Dress code
In general, you should wear suitable clothing when entering a church (in many places, it is considered unacceptable to go inside wearing shorts or a tank-top). We suggest that women carry a shawl to cover up bear shoulders or low-cut tops. It also comes in handy when your shoulders get sunburned!

It is considered inappropriate for men to go without a shirt / T-shirt (other than at the beach).

Trekking poles (adjustable)
Highly recommended. A pair works best, depending on what you are comfortable with. If you suffer from back or knee pain this should be considered essential. Remember to practise walking with your pole(s) on different types of terrain in the months preceding your trip.

Walking boots
The importance of good footwear cannot be stressed enough. Your boots should be sturdy and of good enough quality to handle all types of terrain. Lightweight boots, (cordura/leather boots) which have Gore-Tex or sympatex water-proofing are most suitable for this trip. They should provide good ankle protection and be well broken in. Waxing leather boots regularly prolongs their life.

Walking tops & trousers
We recommend walking trousers and shorts and quick-dry wicking t-shirts. These can be washed easily and will dry overnight and still look good for sightseeing or having a drink in town. Wicking T-shirts are fast drying, keep moisture away from your skin and are available at outdoor stores. You should also bring one pair of loose-fitting trousers to wear in cities and for evenings out, etc. Shorts or zip-off trousers are useful in warmer weather.

Practical info

How to arrive


Arrival:

To reach San Gimignano, the easiest option is to first travel to Poggibonsi train station (Poggibonsi–San Gimignano), which is well connected with Florence and Siena.

From Poggibonsi station, you will find the bus stop for lines 130 (or 133, depending on the schedule), which connect directly to San Gimignano. The journey takes about 20–25 minutes and drops you near the historic centre. Buses run frequently during the day, but it is advisable to check the timetable in advance, especially on weekends and public holidays.

Departure:

Siena is well connected to Florence by both train and bus, with frequent departures throughout the day. The journey takes approximately 1 hour and 15 minutes.

From Florence, you can easily reach Florence Airport (Peretola) or other Italian airports.
 
 
 

Mobile App


Use the SloWays APP for iOS and Android smart phones in combination with the written documentation provided.

The App has the detailed tracks and maps that you can use offline and without roaming. Thanks to the phone’s internal GPS, you can check your exact position on the map, so you always know exactly where you are. It also helps you self-navigate you way while travelling. More information on how to use the App inside the roadbook documents.

The navigation features include:

  • Offline navigation. Mobile data not required after initial download
  • Accurate GPS tracks
  • Autorotation of the maps
  • Daily route summary and elevation chart
  • Panorama of the track and at street level
  • Alarm and vibration that alerts you in case you go off track.
  • Emergency SMS button with position coordinates
  • Possibility to record and take georeferenced photos of problems on route alerting fellow travelers
  • Hotel information
  • Points of interest along the way
  • Historical background

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Touroperating
S-Cape Countryside Travels srl
Borgo Allegri 16R
50122 Firenze FI
P. IVA 05227330486

 
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Touroperating S-Cape Countryside Travels srl Borgo Allegri 16R 50122 Firenze FI, Italy
VAT Nr 05227330486
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