Tuscany 1 itinerary

Day 1

You will be picked up at either Siena or Chiusi and taken to Montalcino, a perfectly preserved walled hilltop town, famous for both its views and its red wine, Brunello di Montalcino. Included in your notes is a short walk around the outside of the town's walls.


Day 2

The first walk takes you down through forests to a Romanesque abbey isolated in fields of wheat and vineyards, which is one of the most beautiful in Tuscany. Your accommodation for the night is in very comfortable apartment (with a home-cooked dinner) in the small village that overlooks the abbey.  (12 kms, 2.5 hrs)

Please note, the viticultural traditions of Montalcino can be experienced at an organic vineyard a short walk (or drive) from your accommodation on Day 2.  This includes a guided vineyard visit plus a variety of tasting in the cellars: 'Welcome to Montalcino' (3 wines, 1.5 hours), 'Terroir Experience' (5 wines, 2 hours); and 'Vertical Tasting' (6 wines, 2.5 hours).  Please contact us for details.

sant antimo

Day 3

Today you climb up through vineyards and olive groves, to a beautifully restored medieval pilgrim town, a key point on the road to Rome, which is now a peaceful agricultural town and one of the most charming in the area. Despite its pedestrian centre, two beautiful Romansque churches and several beautiful gardens, which still remains relatively unvisited.
(12 kms, 3 hrs).

Day 4

Today you follow parts of the medieval road down into the bare, rolling hills of the Val d'Orcia, with sweeping views across the valley to the forests and peaks of Mount Amiata before a short climb up to your base for the evening.  This enchanting little town was the birth place of one of the more important 15th century popes, who  had the modest village razed and then rebuilt in his honour, creating one of the gems of southern Tuscany, a fine example early Renaissance architecture. .
(12 kms, 4 hrs)


Day 5

The last walk takes you through forests to Montepulciano. On the way you pass a tiny fortified village, perfect for lunch. Perched on a hill between the Orcia and Chianina valleys, Montepulciano was an ally of Florence in their relentless war against Siena, and was amply rewarded and has an extraordinary architectural heritage from this period.
(13 kms, 4 hrs).

Day 6

After breakfast at 9.00 you'll be transfered to nearby Chiusi on the main Rome/Florence railway line.

bagno vignoni

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This 6 day walk can be personalised to meet your interests and dates.

  • Cost


    per person
  • Five nights accommodation
  • All breakfasts included
  • 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
  • Pick up at either Siena or Chiusi (on the Rome/Florence rail line) and drop-off at the end back in Chiusi
  • 24 hour backup from local manager

Cost Options

$2750 b&b per person

Single supplement:  $800

** Please note a high season surcharge may apply.

Tour costs quoted are in Australian dollars (AUD)




"I'm back from my holiday and back at work! My walk from Montalcino to Montepulciano was marvellous and, given the opportunity, I'd do it again tomorrow! I've certainly told friends what a great time I had and would recommend it to anyone."

– Bridget N, Tuscany 1 walk

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2. Central Italy: Tuscany 1, from Montalcino to Montepulciano FAQs

Find out a little more about the 2. Central Italy: Tuscany 1, from Montalcino to Montepulciano tour by reading some of our most frequently asked questions.

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2. Central Italy: Tuscany 1, from Montalcino to Montepulciano

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