Tuscany 3 itinerary

Day 1

A private vehicle will pick you up from Florence and take you to your hotel in San Gimignano, a walled medieval town famous for its towers, which was on the Via Francigena, the most important route to Rome in the Middle Ages. In the afternoon there is a short loop walk through the celebrated Vernaccia vineyards with wonderful views over San Gimignano's famous skyline before returning to San Gimignano.  (8 kms, 2 hrs)


Day 2

Today's walk takes you to another well-preserved medieval town that prospered trading on the Via Francigena. The walk leaves San Gimignano via vineyards and olive groves before following a narrow, forested valley.  It passes through a landscape that has changed little since the Middle Ages. (12 kms, 3 hrs)

Day 3

The walk this morning again picks up the route of the Via Francigena, crossing undulating farmlands, passing hamlets, castles and a fine Romanesque abbey before arriving at a tiny walled medieval village, a little gem with a ring of high walls that enclose a precious collection of restored houses, gardens, palazzi and your hotel for the night.  (16 kms, 4 hrs)


Day 4

The walk today takes you to Siena, the dynamic capital of southern Tuscany.  It passes through forests and the range of hills that once protected Siena's northern frontier from their mortal enemies in Florence. A city rich in art and history, Siena grew up around the Campo, its famous scalloped-shaped central piazza.  Siena is a wonderful place to explore or simply while away time, sipping an aperitivo and watching the colourful life pass by.  (12 kms, 5 hrs)

Day 5

Breakfast at your hotel. Siena is connected by rail and bus to Florence, from where you can continue your holiday.

Interested in the 2. Central Italy: Tuscany 3, walking from San Gimignano to Siena Self-Guided Walk?

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This 5 day/4 night walking tour can be personalised to meet your interests and travel dates.

  • Cost


    per person
  • Four nights accommodation
  • All breakfast
  • Reading lists and historical and cultural notes
  • Maps and detailed walking instructions
  • Hidden Italy App with GPS to complement the roadbook
  • Daily transfers of baggage between hotels
  • Pick-up from Florence railway station or Florence airport and transfer to San Gimignano on Day 1
  • 24 hour backup from local manager

Cost Options

$2700 b&b per person

Single Supplement: $800

** Please note a high season surcharge may apply.

Tour costs quoted are in Australian dollars (AUD)




Yes, it lived up to my expectations: first self-guided walk and I loved it. The perfect weather helped of course. Highlights included the ‘challenge’ of doing it ourselves. The hotels we stayed in were lovely; all towns worth a visit in themselves.

– Jill E, Tuscany 3 walking tour

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2. Central Italy: Tuscany 3, walking from San Gimignano to Siena FAQs

Find out a little more about the 2. Central Italy: Tuscany 3, walking from San Gimignano to Siena tour by reading some of our most frequently asked questions.

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2. Central Italy: Tuscany 3, walking from San Gimignano to Siena

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