A self-guided adventure from inn to inn

Self-Guided Hiking in Tuscany

7 nights — from USD1390

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.


  • Explore the hilltowns of Montalcino, Pienza and Montepulciano
  • Take daily walks between hilltowns along a continuous trail
  • Explore the villages of Rocca d'Orcia, Bagno Vignoni, San Quirico and Montichiello
  • Enjoy great Tuscan cuisine and wines
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At a Glance
Depart From: Buonconvento Finish In: Chiusi
Starting Dates: Any day, all year long
Fitness Rating:3-4 Ratings Explained...

“...an absolutely fantastic time...”

testimonial 1

We had an absolutely fantastic time in Italy! We loved the self-guided tour and have no suggestions for improvement since everything went so smoothly. We liked all of the places we stayed and found the suggestions of various things to see in each town very helpful, and the directions for the walks were very easy to follow. It is truly one of the best vacations we've ever had! The Italian people were very friendly, and the countryside in Tuscany is spectacularly beautiful. Thanks for your help in our planning!

— Sally Wing and Jim Sedlacek

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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: 9 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.
Tuscany map

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
  • detailed maps and route descriptions
  • a descriptive guide of the various sites to see
  • a smartphone for emergencies, equipped with GPS and walk coordinates
  • 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. We also tier-price based on your group's size. You can keep your tour private to your own group or you can open your tour for other travelers to join, thereby taking advantage of our tier discounts. 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 1390 390
comfort/select 1690 490
comfort/first class 1990 690
first class 2390 790


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).

“...one of the best vacations ever...”

testimonial 2

Peggy and I had a fantastic walking tour in Tuscany! We want to give everyone in the Girosole organization who helped contribute a big "molto bene" for making this one of the best vacations ever. It's obvious that Girosole had done a lot of research on the route, towns, accommodation and ristorantes. Everything that Girosole provided was first class. But what stood out for us was the customer service. We highly recommend Girosole and hope we'll have the opportunity for returning - perhaps to explore Cinque Terre next time. Thanks once again for a memorable vacation.

— Robert Leppan and Peggy Dodds

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.

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(Feel free to tell us about yourselves, for instance whether you've been to Italy before, have taken a walking tour, your interests; whatever you think might help us help you have the best trip of your lives.)

"Woodpile" by Michelangelo

Tuscany walking