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

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 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
  • Hidden Italy App with GPS to complement the roadbook
  • 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

$2900 b&b per person

Single supplement:  $800

** Please note a high season surcharge may apply.

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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