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

The traditional dishes of Tuscany are Italy's most influential cuisine.  The ingredients and techniques of the region have made their mark not just on the menus of the rest of Italy but also abroad, even in France.  The produce is of the highest quality, with its mushrooms, truffles and prosciutto especially prized.  Wine has always been central to Tuscany's economy and way of life, familiar names like Chianti and Brunello are just a portion of their enormous output.

Generous breakfasts are included each day (you'll need them for your walks).  Hidden Italy will provide you with a curated list with descriptions and locations of three to four restaurants for each town/village you visit (from fancy to more relaxed).  This information will be on the Hidden Italy walking App and you will be able to book your meals directly through the App.

Support on the walk

Support on the walk

To guide you through this wonderful walk, you will receive:  the Hidden Italy roadbook (an eighty-page A5 booklet that includes comprehensive daily walking notes accompanied by detailed maps, updated and revised each year);  access to the exclusive Hidden Italy App to complement the roadbook (the App is downloadable to Apple and Android devices and features information about the routes: maps, GPS tracks, altimetric profiles, etc; GPS navigation on all the routes; an alert function if you stray off the track; and an emergency function);  twenty-four-hour phone support from our Florence-based Operations Manager.

Booking conditions

To confirm the booking, a deposit of 25% of the total booking cost is required within 7 days of the issue of the invoice.  Please note that in the event of customer cancellation, deposits are refunded, less a cancellation fee of $500 per person per tour.  Click here for full T&C’s

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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