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.

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:

We require a $500 per person non-refundable deposit to confirm the booking.  Should government COVID-19 travel restrictions prevent the tour from operating, the tour will be rescheduled.  In the event the new dates are not suitable, you will have the option of a credit note for the amount paid which can be used towards future tours or a full refund, minus the deposit which will be held as credit for future tours.  Click here for full T&C’s

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

Don't miss out, places are limited. Make your booking now. Book Now › Make an Enquiry ›
Print Friendly

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

$2050 B&B only p/p


$2260 with dinners included p/p

Single Supplement: $600




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

View all Testimonials ›

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.

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

Hidden Italy - travelling to Italy in 2022

Keep up to date with the latest news from Hidden Italy and any upcoming events.

Subscribe to our e-newsletter

Sign up for our newsletter to receive regular updates, travel tips, info on local events and discounts on our popular tours.

Our People

Get to know some of the people who make Hidden Italy Walking Tours happen.