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Walking Tour in Chianti Tuscany - Florence to Siena

(6 days / 5 nights - $2,090 AUD per person or $1,890 AUD with 'No Dinners' Option)



Manarola, Cinque Terre

Walking Between Castles

This walking tour in Tuscany can be personalised to meet your interests and travel dates.

This magnificent walk starts in Renaissance Florence and finishes in medieval Siena, two of the most beautiful cities in Italy – passing through some of the most celebrated countryside in Europe, a unique landscape of rolling hills, vineyards, olive groves, forests, isolated farmhouses, medieval market towns and ancient villages, moulded by over three millennia of settlement.

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 toswns in Italy, magnificent abbeys and famous castles.

As Florence and Siena are both sizable cities surrounded by modern development and not easy to leave and enter on foot, you will be picked up from Florence and taken to Impruneta on Day 1 and dropped in Siena on Day 6. Please note that there also points leaving and entering several towns where you'll have to walk up to two kilometers on lightly trafficked asphalt roads.


What's included in this walk?
  • five nights accommodation
  • all breakfasts and dinners (except on Day 4)
  • recommendations for lunch
  • 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
How hard are the walks?

All the walks follow well-marked paths, generally along quiet graded country roads. Orientation is straightforward. Several of the walks are over 15 kilometres long and there are several sustained climbs- a Grade 3 walk.
What's the accommodation like?
Accommodation is in good, welcoming 3-star family run hotels, which themselves are part of the history of the region, except for the penultimate night where you will stay in one of the finest hotels in the Chianti, a magnificent 4-star hotel set in a restored 11th century convent, surrounded by some of the most famous vineyards in Tuscany – a fitting finale to your visit to the district. Costings are calculated on two people sharing a double room. All rooms have an en suite bathroom.



Tour Cost: AUD $2,090 per person (single supplement $350)
Tuscany 4 'No Dinners' Option : AUD $1,890 per person




  Tour Snapshots:  (click the image for a larger version)



Vernazza, Cinque Terre

Walking Between Castles


Fish markets, Cinque Terre

The Start of Your Final Walk


Portovenere Bay, Cinque Terre

Piazza Metteotti


Vernazza Bakers

Lunchtime on Day 4


Houses, Riomaggiore

Florence, The Ponte Vecchio


Portovenere, Cinque Terre

Chianti's Most Famous Product


Vernazza houses

Accommodation in the Chianti Hills


Approaching Portovenere

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Vernazza houses

A Farm on the Way


Approaching Portovenere

Walking to the Chianti Hills




The Tuscany Walking Tour - Florence to Siena Itinerary

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Day
  

Transfer from Florence to Impruneta (11 kms away). Dinner in Impruneta, a pleasant town a short drive from Florence. Your hotel has views of the town’s famous basilica in the central piazza, dating from the 11th century, which contains a miraculous image of the Madonna, fragments of the True Cross and masterpieces by Luca della Robbia and Michelozzi.

Day
  

A long walk over undulating hills, through forests, vineyards and wheat fields to Greve in Chianti, passing a small market town (where you can break) and one of the oldest and wealthiest abbeys in Tuscany finishing for the day in one of the centres of wine growing in the region. Your hotel overlooks the main square, Piazza Matteoti. (5.5 hours)

It is possible to shorten this walk by staying overnight in the very pleasant small agricultural town you pass through after two hours walk from Impruneta.

Day
  

Today’s walk starts with a long climb to the ridge of the highest range of hills in the Chianti district, passing through hamlets and forests on the way. From here you are rewarded with spectacular views over the valley of the Greve River. You continue along the ridge following the route of a Roman road, passing through pines forests and past the ruins of an 11th century abbey until you reach the highest point of the Chianti. Your accommodation is nearby, a simple but lovely agriturismo set in what was originally a 10th century abbey, with its own parklands, small swimming pool and a celebrated restaurant. (3.5 hours)

You may like to extend your stay by a day at the agriturismo to enjoy this peaceful location by adding another walk. This 4 hour loop walk takes you down in the valley, through pine and chestnut forests, to a delightful, ancient village with an excellent restaurant where you can relax and have lunch before visiting the medieval castle on the way back to your base.

Day
  

An easy day, continuing along the ridge heading down through pine and oak forests, past a hamlet that sits on the historical border between Siena and Florence, until you emerge at a magnificent wine estate in a converted medieval abbey, where you can have a light lunch. Your base for the night is another pleasant market town an hour’s walk further into the valley, passing through more forest and farm lands. You stay in one of the best hotels in the Chianti, a beautiful 4-star hotel set in a converted 11th century convent. (3.5 hours)

Day
  

Today’s fascinating walk takes you past three famous medieval castles (each now the seat of major wine estates). You start walking through classic Chianti countryside passing vineyards, farm houses with panoramic views before climbing up into chestnut, pine and oak forests and finally descending to a splendid castle, which has been in the Ricasoli family since 1141 and in whose vineyards the Chianti Classico wine was first developed in the 19th century. Your accommodation is in a lovely b&b in a tiny hamlet under the walls of the castle. Dinner tonight is a fitting finale in castle's restaurant a short walk from the hamlet. (4.5 hours)

Day
  

This morning, after breakfast, you will be transferred to nearby Siena.


Contact Us

For more information on this tour or to make a booking, please get in touch with us.