Monte Oliveto Maggiore to Montalcino

  • Monte Oliveto Maggiore  - © William Mackesy
  • Hilltop Chiusura  - © William Mackesy
  • Chuisura - © William Mackesy
  • Clifftop roadsign - © William Mackesy
  • Ridgetop track  - © William Mackesy
  • Acacia, believed - © William Mackesy
  • Rosebush - © William Mackesy
  • Ridgetop track - © William Mackesy
  • Monte Amiata in distance  - © William Mackesy
  • Track - © William Mackesy
  • Icon - © William Mackesy
  • Up the ridge  - © William Mackesy
  • More ridgeway - © William Mackesy
  • Big view north - © William Mackesy
  • Icon again - © William Mackesy
  • More flowers - © William Mackesy
  • OK, that icon again!  - © William Mackesy
  • From Montalcino hotel, morning  - © William Mackesy
  • Montalcino, morning - © William Mackesy
  • Tuscan cliche - but what a joy  - © William Mackesy

Key information: Monte Oliveto Maggiore to Montalcino

  • A fine walk from a famous monastery to Montalcino on its hilltop, through classic Tuscan landscape.
  • Bask in the beauty of the rolling hills, with their big views, medieval villages and hilltop farmhouses. Enjoy!

Walkopedia rating

  • Walkopedia rating89
  • Beauty30
  • Natural interest15
  • Human interest14
  • Charisma30
  • Negative points0
  • Total rating89

Vital Statistics

  • Length: 23km
  • Maximum Altitude: N/A
  • Level of Difficulty: Moderate
Chuisura - © William Mackesy


A fine day's walking to the side of the old Via Francigena pilgrimage trail.

The landscape includes forests, meadows and vineyards littered with ancient farmhouses and hamlets, often perched on knolls and hilltops. It supports a varied and very characteristic selection of plant and animal life, from wild boar through to mellifluous nightingales, from mixed forests thick with scented wildflowers and herbs to bosky hedgerows and those classic lines and huddles of cypresses.

Start at the famous monastery of Mont Oliveto Maggiore up in high and wild country to the east of the Via Francigena.  The walk is immediately gripping, winding round and up to the nearby hilltop village of Chuisure, a charming place of tiny squares of old brick houses, with pauses to take in the full drama of the monastery on its cliff-surrounded promontory.

Then you follow strade biance then farm tracks on long, often open ridges affording wonderful views of eroded limestone cliffs and little gorges, and rolling hills patched with fields and woodland, each hilltop bearing a farmhouse or hamlet.

A long, steady descent through more lovely landscape will take you into the deep Serlate valley. Next is a long climb on farm tracks through more open country, a mix of meadows and cereal fields with woods in the sharp little ravines below, to another highland complete with wide views and a blink-first competition with Montalcino on its wooded hill, a patchwork of fields and farmhouses on its lower slopes. Then you must tackle Montalcino's steep, thousand-foot (well, that's how it seemed) hillside. It is a slog. The delights of Montalcino and its outstanding view will soon wipe away the pain.

See William Mackesy's account  for a detailed feel of what this walk is like.

For more information and photos, including detailed practical information and some warnings, see our Via Francigena walk pages.

Other accounts: share your experiences

Your comments on this walk, your experiences and suggestions, and your photos are very welcome. Where appropriate, you will be credited for your contribution.

Safety and problems: All walks have inherent risks and potential problems, and many of the walks featured on this website involve significant risks, dangers and problems. Problems of any sort can arise on any walk. This website does not purport to identify any (or all) actual or potential risks, dangers and problems that may relate to any particular walk.

Any person who is considering undertaking this walk should do careful research and make their own assessment of the risks, dangers and possible problems involved. They should also go to “Important information” for further important information.

Big view north - © William Mackesy

Anyone planning an expedition to this place should see further important information about this walk.

Monte Oliveto Maggiore  - © William Mackesy...

Responsible travel matters, a lot. How you travel will make a real difference - for better or worse. PLEASE consider this when making plans. Read more

Our partners Responsible Travel 

have carefully chosen expeditions 

and holidays around the world.    

Great walking, and much else...

Walkopedia Sponsor

See their site for inspiring ideas.

For £100 off your trip, contact them quoting WW50

All material on this website is © Walkopedia Ltd 2008 - 2020, unless specified otherwise.