Tuscany 2 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

A gentle walk over undulating hills of northern Tuscany, passing through vineyards, wheat fields and forests to arrive at a small market town.  (9 kms, 2.5 hours)

Day 3

Today you continue though vineyards and forests passing through the heart of the Chianti district. The walk finishes at a small town that is one the centres of wine growing in the region (12 kms. 3.5 hours).  There is a longer version which enables you to visit one of the oldest and wealthiest abbeys in Tuscany, where you’ll have the chance to break your walk to visit the abbey and have lunch at their excellent restaurant (there is also a simpler bistrot nearby (16 kms, 4.5 hours).


Day 4

Today’s walk starts with a long climb up to the ridge of the highest range hills in the Chianti district.  On the way, you pass a medieval castle and several hamlets hamlets.  From here you are rewarded with spectacular views over the valley of the Greve River.  You continue along the ridge climbing gradually, passing through forests on the way to your accommodation, a lovely ‘agriturismo’ with a swimming pool.  (12 kms, 3.5 hours)

Day 5

Today you continue along the ridge past the ruins of an 11th century abbey, until you reach Monte San Michele, the highest point of the hills.  From here, you continue along the ridge heading down through pine and oak forests, until you emerge at a magnificent wine estate in a converted medieval abbey, where you can have lunch and sample some of their produce.  Your goal, another small town devoted to wine production, is an hour’s descent through an oak forest and farm lands.  Along the way you pass from the Florentine Chianti into the Sienese Chianti.  (19 kms, 5 hours)


Day 6

This is a short walk, which will get you to Siena at lunch time, leaving plenty of time to explore this extraordinary city in the afternoon.  Today you walk through classic Chianti countryside passing more vineyards, farm houses with panoramic views and a beautiful castle along the way.  You will be picked up at a hamlet at the end of the walk at 12.00 pm and driven to Siena, 10 kms away.  (8 kms, 2 hours)

Day 7

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

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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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