Day 6 - looking back at Rocca d
Day 6 - looking back at Rocca d'Orcia (Judi Dalton) 
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£785.00 (2017)
Per person
7 nights
7 B&B, 1 evening meal, 1 picnic, luggage transfers between hotels
3 ½ - 6 hrs per day
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Southern Tuscany (Italy)
Renaissance hilltop towns and classic wines
Full Description

A self-guided hike through the southern Tuscan hills, staying at the best renaissance towns - Siena, Montalcino, Bagno Vignoni, Pienza, Montepulciano.  Vist the Abbeys of Monte Oliveti and Sant' Antimo, taste local cuisine and Tuscan wines.


Grade:  Medium or easy-medium


Southern Tuscany - Renaissance hilltop towns and classic wines 

The Tuscan landscape at its most evocative – rolling hills protected by dramatic hilltop villages, whose very stones reek of medieval power struggles and intrigue. And to assist in the consideration of these issues, two fine red wines, the rich Brunello di Montalcino and the Vino Nobile di Montepulciano, with their vineyards at the heart of our walk. From Siena, through Montalcino, the Abbey of Sant’ Antimo, Bagno Vignoni and its ancient thermal baths, Pienza and a final walk up from the church of San Biagio to the cathedral at Montepulciano. We recommend extra nights in most places to explore the treasures of these towns as well as to relax and to eat and drink well. Walked by On Foot staff: Simon and Debbie


For Alan MacLeod's photo album of his 2016 walk click here.


Standard option  (as per "Itinerary"): 7 nights, but why not stay extra nights in the hilltop towns and make your progress more leisurely? 


Shorter options:

6 nights (miss night 1 in Siena and travel straight to Buonconvento);

5 nights (miss nights 1 (Siena) and 4 (second Montalcino night) – miss days 2 and 4 (Sant' Antimo) walking.

4 nights stay Montalcino, Bagno Vignoni, Pienza and Montepulciano, walk days 5, 6 and 7

  • Siena, the Campo and cathedral
  • The rolling hills of Southern Tuscany
  • Brunello di Montalcino
  • Pienza, the classic Renaissance hilltop town
  • Montepulciano, San Biagio and the cathedral

WE RECOMMEND: An extra night in Siena at the start to explore this historic and beautiful city, extra nights at Pienza or Montepulciano, classic hilltop towns, at Bagno Vignoni to take the waters, or at Buonconvento to relax, swim in the pool and watch the sunset over the Tuscan hills.  Wine tasting in Montalcino or Montepulciano (your host will advise the best places...)


EATING AND DRINKING in Tuscany can be very sophisticated and it is sometimes difficult to find an authentic regional dish, though Leonardo at Pieve a Salti (night 2) thinks differently - "all our food is grown on our farm if at all possible - we have the largest organic farm in the region.  My favourite dishes here are Penne con ragù di Cinta (pork ragout) or Pici with ragù all’aglione (tomato and garlic ragout), Zuppa di farro (spelt soup), Cinghiale in umido (wild boar), Rasato al Brunello (veal with Brunello Wine) - all of which are Tuscan specialities.  And of course you must have some wine - Brunello di Montalcino - the vineyards are just down the road!"

Route map
Southern Tuscany (Italy) route map
Route designed by

Daniele Cavazzoni

Daniele's early passion for nature led him to explore all the Italian regions on foot. He started working as a nature guide for an international tour operator, working around the Indian Ocean and in the African savannah.


He then decided to come back to Tuscany, and currently works as a hiking & birdwatching guide in Tuscany, as well as working on the family organic "pecorino" farm, in the middle of the forest.