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from £1285
The Via Francigena, the way of Saint Francis, is the pilgrimage path that leads from Canterbury to Rome. 

Guided Walking Holidays - A Trail Through Ancient Tuscany

The gently rolling scenery opens in front of you with views sweeping across vineyards and fields of sunflowers to San Gimignano, one of the most famous skylines in Tuscany. This is a scene changed little since the first pilgrims walked this way following the way of the Franks to Rome from Canterbury. The route was first documented in 876 AD, so you won’t be the first to walk this way. The Tuscan lands remain as abundant as ever and the patchwork of fields in contrasting pastel shades are much as they would have been. This is the way to experience Tuscany, all with Ramblers Walking Holidays.

The evidence of pilgrims through the ages is everywhere. The weather-beaten marks on a farm house wall that only the sharpest pair of eyes will notice. The ancient towns of San Miniato and San Gimignano, made wealthy by passing pilgrims. The glorious Renaissance architecture of Siena is a suitable highpoint on which to finish. Here the triumph of what man has created rivals the glories of nature experienced on the walk.

Holiday Highlights

  • Look out for signs left by pilgrims through the ages.
  • Enjoy the first view of San Gimignano’s towers across the Tuscan countryside.
  • Savour the gastronomic delights of the heart of Tuscany.
  • Stroll around Siena. A feast for the senses.
The holiday inclusions and exclusions at a glance
What's included in this holiday Items that are covered in the cost of holiday price.

      Return flights from Heathrow to Pisa (British Airways) , Manchester to Pisa 01 Oct 19 (Easyjet)
      Airport transfers
      Baggage transfers between centres 
      Half board en suite accommodation 
      All local transport costs.
Whats not included in this holiday Items that are not covered in the cost of holiday price.

  • Entrance fees to some museums and historic buildings (unless otherwise specified)
  • Personal expenses (such as your bar bill)
  • Discretionary tips
  • Optional excursions
  • Insurance
Please select Departure Date to view:

Please see Holiday Information Sheet for this holidays individual departures itinerary (located under View Departures & Book tab)

Whilst every effort will be made to adhere to the outlined itinerary and advertised programme, local conditions can change due to weather or other unforeseen circumstances. This may mean that routes and timings need to be amended or the order of days may change, sometimes at short notice.

This departure: Grade 5

  1. Day 1

    We fly to Pisa and transfer by road to San Miniato. The drive takes inland along the Arno Valley towards Florence. About half way we turn right up the impressive south side of the valley into San Miniato perched on the hills above the valley. Hopefully we have some time to look around.

  2. Day 2

    The Via Francigena for the first 5km south of San Miniato follows a major road so we start our day by private coach to bypass this section before we start our walk to Gambassi Terme. The track undulates effortlessly through olive groves and vineyards. Most of the time we walk on a ridge with open, distant views of quintessential Tuscan scenery in most directions. On arrival in Gambassi we will be met by private transport to take us on to San Gimignano where we stay two nights. 21km (13  miles); 500m↑ 400m↓; 6 hours.

  3. Day 3

    In the morning we take transport back to Gambassi Terme. From here we continue our way towards San Gimignano today. Today is an easier walk, shorter, shadier and with less ascent. The scenery is wonderful again: more vineyards, more olive groves, hills dotted with farmhouses and cypresses, distant views of higher mountains. This area feels affluent and sophisticated: no abandoned buildings here but luxurious ‘agriturismo’ hotels in superbly renovated farmhouses. 14km (9 miles); 200m↑ 230m↓; 5 hours.

  4. Day 4

    Today the trail leads us to Colle di Val d'Elsa. There are no steep uphills and there is quite a bit of shade. The scenery changes subtly about half way: more woods, fewer vineyards, fewer olive groves. A good way to organise the day is to spend the morning enjoying the delights of San Gimignano and then set off late morning. This would get us to Colle mid afternoon with time to explore. Particularly look out for the lift which takes you up to the upper town. 11.5km (7  miles); 150m↑ 300m↓; 5 hours.

  5. Day 5

    Continuing through little villages we walk to Monteriggioni. This is another gentle day across easy terrain. The outline of Monteriggioni is visible from some distance and makes an impressive goal for the day. Our accommodation will be in a local village so from Monteriggioni we will be transported to where we stay. 14km (9 miles); 200m↑ 150m↓; 4 hours.

  6. Day 6

    This is a long but pleasant last stage, with a lot of walking on narrow tracks or forests paths. Vineyards and olive groves are getting thinner on the ground but the scenery is still lovely as you meander from woods to fields. There are plenty of sights (castles, towers) along the way as well. Siena is built on higher ground and can be seen from some way away. The city is a spectacular as its reputation suggests. 19km (11.8 miles); 300m↑ 300m↓; 6 hours.

  7. Day 7

    A day of leisurely sightseeing in Siena. There is plenty to see, the Duomo with distinctive striped marble exterior and the Campo are highlights. For those feeling fit a climb up the 97m Torre del Mangia above the Campo offers good exercise and unrivalled views over your route to Siena. Also be sure to try some Panforte, Siena's most famous contribution to world cuisine. 

  8. Day 8

    Our transfer back to Pisa will be by road. It should take about 2hrs.

Travel Details

  • Return flights from Heathrow to Pisa (British Airways) 
  • Airport transfers by road c. 1 hour
  • Upgrades are available on most flights. For scheduled flights this may be Premium Economy, Business or First Class. Most low-cost carriers also have extra legroom seats.
  • If direct regional flights are not available, we can often offer add-on flights to a London airport at a competitive rate. Please ask us for details and a competitive quote.

Trip Map

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Our Accommodation on this holiday

Below is the accommodation featured on this holiday. If you are on a multi-centre holiday, these are highlights of the places where we stay. Please refer to your Holiday Information sheet (which can be found under View Departures & Book), for your departure date and for all your accommodation details.

Hotel La Cisterna, San Gimignano

A final accommodation list will be provided with your travel documents, but a hotel that we are likely to use, and an indication of the tourist class hotels used, is the Hotel La Cisterna. This hotel is located at the cultural centre of San Gimignano, the beautiful and historical Piazza della Cisterna, where you feel like you have stepped back in time. The hotel stands in a 12th century building, with the coming and goings of citizens in view, but is surprisingly modern inside. Some rooms have magnificent views over the town and surrounding Tuscan countryside. All have complimentary Wi-Fi, Florentine design, air conditioning, mini bar, satellite TV, safe and en suite bathrooms. Breakfasts and dinners are included in the holiday charge, and are served in the restaurant which that specialises in excellent Tuscan cuisine, using fresh, seasonal and local produce. Breakfasts are served in a 14th century dining room, with magnificent views over the San Gimignano countryside.