Chianti walking tour

Starting in Florence this classic 7 day walk takes you through the Chianti via some of the most celebrated landscapes in Italy.

tuscany 2 strip

This magnificent walk passes through some of the most celebrated countryside in Europe, a unique landscape of rolling hills, forests, vineyards, olive groves, isolated farmhouses, medieval market towns and ancient villages, all moulded by over three millennia of settlement. You will be picked up in Florence and taken to Impruneta on Day 1 and dropped in Siena on Day 7.

greve strip

The Chianti is not only a place of extraordinary natural beauty, it is also very rich in history.  It has been inhabited since the Etruscan times, but its formative times were in the Middle Ages, when it was settled by some of the most powerful monasteries of the times and was the battleground for fighting between the ambitious cities of Florence and Siena.  On the walk, you pass some of the most attractive villages and towns in Italy, magnificent abbeys and famous castles.

The walks

The walks

This is a grade 3 walk (click here for details). The walks are from 9 to 19 kms (2.5 to 5 hours). Except for the first day, most of the trail is clearly marked with walking signs. It generally follows good unsealed country roads, although there are several sections which wind along smaller paths. There are no steep climbs although on Day 3 there is a sustained walk up to the ridge of the Chianti Hills. Much of Day 4 winds through forests.

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

The accommodation

The accommodation

The Hidden Italy use the best accommodation available.  This includes a combination of family-run 3-star hotels, 4-star hotels in restored historical buildings and lovely country ‘agriturismo’s with swimming pools and fine local cooking.  All rooms have, private ensuite bathrooms.  Guaranteed!

The food

The food

You are in the heart of the Chianti district so the food and wine is magnificent.  Generous breakfasts are included each day (you'll need them for your walks).  With 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 2 the Chianti, from Florence to Siena Self-Guided Walk?

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This 7 day walking tour can be personalised to meet your interests and travel dates.

  • Cost


    per person
  • six nights accommodation
  • all breakfasts
  • reading lists and historical and cultural notes
  • maps and detailed walking instructions
  • daily transfers of baggage between hotels
  • transfer from Florence to Impruneta, Day 1; transfer to Siena, Day 6
  • 24 hour backup from local manager

Cost Options

$2260 B&B only p/p


$2570 with dinners included p/p

Single supplement:  $650


Tour costs quoted are in Australian dollars (AUD)



The tour exceded our expectations. It was the combination of beautiful country for walking, excellent accommodation, great food and wine that for us was the perfect mix. The notes are excellent and made a huge difference to our enjoyment of the walks

– Mike B, Tuscany 2 walking tour

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2. Central Italy: Tuscany 2 the Chianti, from Florence to Siena FAQs

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

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2. Central Italy: Tuscany 2 the Chianti, from Florence to Siena

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