A self-guided adventure from inn to inn

Self-Guided Hiking in Tuscany

7 nights — from USD1460

Our self-guided hike through Tuscany (a more challenging version of our popular self-guided walk in the same region) takes you on a grand tour through the Val d’Orcia, famed for its hilltowns and breathtaking landscapes. The full tour covers a continuous trail, with a new leg each day, setting out from the 13th C. monastery of Monte Oliveto Maggiore and finishing in the hilltown of Montepulciano, some 65 miles later. You can also opt to do just a portion of the walk. Either way, we provide you with all the tools you need to help you put your spirit of adventure into action.

Itinerary Outline

Here is an outline of a suggested daily itinerary. You can shorten or lengthen this tour to fit your travel dates. For further information, please request a detailed itinerary.

  • Day one: You start in Buonconvento, which you can easily reach by train from Siena, Florence, or Pisa. After meeting with your GIROSOLE rep, you visit the monastery of Monte Oliveto Maggiore, after which you walk back to Buonconvento for your first night’s stay. (Walk distance: 7 miles/11 km – climb total: mostly descent)
  • Day two: You walk to Montalcino, across a gently rolling landscape of wheat and sunflower fields. (Walk distance: 8.7 miles/14km – climb total: 1700 ft/530 m)
  • Day three: Your walk today takes you to the small village of Castelnuovo dell’Abate, near which sits the beautiful romanesque church of Sant’Antimo, built of alabaster and travertine. (Walk distance: 7.5 miles/12km – climb total: 450 ft/150 m)
  • Day four: From Castelnuovo dell’Abate, you continue to Rocca d’Orcia, brooded over by its castle keep. (Walk distance: 8.5 miles/13.5 km – climb total: 1800 ft/560 m)
  • Day five: From Rocca d’Orcia, you pass through Bagno Vignoni, which is built around thermal springs in use since Roman times, and arrive in San Quirico, a small agricultural village filled with gardens and charming streets. (Walk distance: 8 miles/13 km – climb total: 1300 ft/400 m)
  • Day six: You set off for Pienza, the hometown of the 15th C. Pope Pius II, whose experiments with urban renovation gave an impressive new face to this little town. (Walk distance: 5 miles/8 km – climb total: 980 ft/300 m)
  • Day seven: Your last day of walking brings you from Pienza to Montepulciano, home to the Sangiovese Vino Nobile di Montepulciano. (Walk distance: 8.5 miles/13.5 km – climb total: 1070 feet/330 m)
  • Day eight: We help you on your way to your next destination with a transfer to Chiusi on the main Rome-Florence train line.

What’s Included

We suggest the following inclusions based on the proposed itinerary (above) and prices (below). Keep in mind that you can modify these as per your own preferences.

  • 7 nights accommodation with en-suite facilities
  • 7 days of walking
  • breakfast each day
  • GPS app with walk coordinates and emergency contact
  • detailed maps and route descriptions
  • a descriptive guide of the various sites to see
  • a Tour Rep to oversee your tour and move your luggage each day
  • travel guidance for pre/post-tour activities

(Not included are airfare, wine and other beverages with alcohol, personal purchases such as laundry, phone calls, frigobar items etc., and anything not specifically included above.)


We price this tour for the following categories of accommodation. You can keep your tour private to your own group or you can open your tour for other travelers to join. Single Supplements (sing. supp.) are charged on single occupancy rooms only. All prices are quoted per person in USD.

accomm. level 2+ p sing. supp.
comfort 1460 410
select 1780 510
select/first class 2090 720
first class 2550 830

You can schedule this tour to start on any day of the week, all year long. As with all our tours, you tell us the dates you would like to start your tour, allowing you the maximum in flexibility and convenience (full explanation).

What's next?

Write to us using the form below, and we'll send you the detailed itinerary for this tour and other relevant information. Or proceed to our booking area to book this tour now.