San Gimignano to Siena

Starting with a transfer from Florence this trail takes you through the famous Tuscany countryside: forests, olive groves, vineyards and the famous rolling hills - a classic walk!

The Tuscany 3 walking tour passes through the heart of medieval Tuscany, starting in the marvelous towered town of San Gimignano and finishing at the dynamic regional capital, Siena. On the way you will visit a town strategically perched above the Elsa River which grew rich during the Middle Ages on its wool and glass and an eerie fortress-village, which was the Sienese stronghold against their implacable Florentine enemies.

monteriggioni strip

The route follows the Elsa valley passing through the vineyards, olive groves and wheat fields, across the Elsa River and through woods. The final day's walk skirts through thick oak and birch forests before climbing up to the walled city of Siena, 'the most perfectly preserved medieval city in Europe'.

The walks

The walks

This is a Grade 2 Walk (click here for details).  It generally follows marked unsealed country roads through rolling hills and farmland, passing through villages and hamlets along the way.  The walks range from 8 kilometres to 16 kilometres and take from 2.5 to 5 hours.  Several of the walks are long but there are no steep climbs and you have plenty of time to enjoy them.

The self-guided itineraries are rewalked and the notes updated each year.

The accommodation

The accommodation

Hidden Italy uses the best accommodation available and the accommodation on this walk is one of the higlights.  You'll being staying in in the best hotels in each place,all in restored historical palazzi in the heart of each town and village, some dating from the Middle Ages and all steeped in the wonderful history of Tuscany.  All rooms have ensuite bathrooms.

The food

The food

You'll have plenty of opportunities some of the most famous food and wines in Italy. Generous breakfasts are included each day (you'll need them for your walks) and with a bit of notice, the hotels wil be able to prepare a cut lunch for the walk.  Dinners are not included in the standard tour, however, if you select the 'Dinners option' (which we strongly recommend) this will include 3 course meals alla carte (ie free choice) in some of the finest restaurants in the area.  The dinner option also means you'll have a guaranteed booking each night.

Guided city tours in Siena and Florence

My friend and colleague Anna, the Hidden Italy operations manager, is a fully qualified guide for both Siena and Florence and is now available for private tours to these two extraordinary cities.  If you would like to book a tour, email:  Click here for a profile of Anna.

"But most of all Anna is marvelous - such an excellent guide and companion. She brings the history to life and she is a lovely, lovely woman."  Melissa and Bob C (Florence and Siena).

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

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This 5 day 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
  • 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

$1700 b&b or $2020 with dinners

Single Supplement: $550

5% discount when 4 or more book and deposit together.



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

July 2019: Rieti and the most beautiful province in Italy

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