Tuscany 4 itinerary

Day 1

Transfer from Florence to Impruneta a pleasant town a short drive from Florence. Your family 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 2

Today is a gentle start to your Chianti visit, a short walk over undulating hills, through forests, vineyards and wheat fields to  a small quiet farming town.  Your accommodation is in a small family-run b&b in the centre of the town.  (2.5 hrs, 6 kms).

Day 3

Today you walk enter the heart of the Chanti district, walking through vineyards and past one of the oldest and wealthiest abbeys in Tuscany (where you can have lunch and visit) before finishing for the day in in a busy market town, one of the centres of wine growing in the region. Your hotel overlooks the main square. (3.5 hrs, 12 kms)


Day 4

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. Unfortunately the small hotel here closed over winter.  You will be picked up at the abbey at 15.00 and taken back to where you stayed Day 3 for another evening. (3.5 hrs  9kms)

Day 5

You will be picked up at your hotel in Greve and taken to Villa San Michele at 09.00.  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 down into the valley. (3.5 hrs, 10 kms)


Day 6

Today’s fascinating walk takes you past three famous medieval castles (each now the seat of a major wine estate). 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 finishing at 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 walk finishes in a small village under the castle, where you'll be picked up from and driven to Siena in the afternoon. (3 hrs, 7 kms).

Day 7

This morning, after breakfast, you ill be able to continue your holiday - Siena is connected to Florence and Rome by regular buses and trains.

Interested in the 2. Central Italy: Tuscany 4 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

$1890 b&b and $2170 with dinners included

Single supplement:  $650

5% discount when 4 people or more book and deposit together.


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 4 walking tour

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2. Central Italy: Tuscany 4 the Chianti, from Florence to Siena FAQs

Find out a little more about the 2. Central Italy: Tuscany 4 the Chianti, from Florence to Siena tour by reading some of our most frequently asked questions.

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2. Central Italy: Tuscany 4 the Chianti, from Florence to Siena

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