A self-guided adventure from inn to inn

Self-Guided Walking in Tuscany

7 nights — from USD1390

Our Self-Guided Tuscany walking tour is a more relaxed version of our hiking tour in the same region: the Val d'Orcia, famed for its hilltowns (like Pienza, Montalcino and Montepulciano) and for its breathtaking landscapes. You start the tour with a night in Siena and then walk in stages through the Val d'Orcia, with stops of two nights in Montalcino and San Quirico, and your final night in Montepulciano. 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 Siena, Montalcino, Pienza and Montepulciano
  • Take daily walks, from one hilltown to the next
  • Explore the villages of San Quirico, Bagno Vignoni and Montichiello
  • Enjoy great Tuscan cuisine and wines
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At a Glance
Depart From: Siena Finish In: Chiusi
Starting Dates: Any day, all year long
Fitness Rating:2-3 Ratings Explained...

“...incredibly scenic...”

testimonial 1

We loved Italy and wish we could have spent more time. Everyone at Girosole was extremely polite and helpful, you helped make our trip truly memorable. We have to really thank Paolo who was always on time, courteous, and willing to help us with restaurant or travel information. He always managed to transport our baggage without ever a problem, and there were never problems checking into our rooms. The walk thru the Val d'Orcia was incredibly scenic, and from Rocca d'Orcia you overlook it all. We managed to eat our way thru Siena, Montalcino, San Quirico, Pienza and Montepulciano and the great perk of it all was that the walking burned it all off. We had many enjoyable picnics like this one in our photo of the Cappella di Vitaleta, which your walking directions led us to one fine day outside Pienza. The scenery was so beautiful, and we have tons of pictures and video to remember our trip by. So thanks again and good luck with the coming season!

— Vin Martiny

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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 with arrival in Siena, arguably one of Italy's most beautiful hilltowns, where there is plenty to do and see. You'll not want to miss seeing the Campo, Siena's remarkable central square, and the Duomo, with its stunning facade.
  • Day two: Your tour rep arrives mid-day to bring you to Montalcino, where you enjoy a warm-up walk in the surrounding countryside, famous for the production of Brunello wine. (Walk distance: 3.5 miles/6 km - climb total: 1070 ft/330 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. You return to Montalcino for a second night. (Walk distance: 7.5 miles/12km - Climb total: 1070 ft/330 m)
  • Day four: From Montalcino, you walk to San Quirico, a small agricultural village filled with gardens and charming streets. (Walk distance: 8.5 miles/13.5 km - climb total: 580 ft/180 m)
  • Day five: Today you enjoy a ring walk in the area of San Quirico and Rocca d'Orcia, passing through Bagno Vignoni, which is built around thermal springs in use since Roman times. (Walk distance: 8 miles/13 km - climb total: 1560 ft/480 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: 1140 ft/350 m)
  • Day seven: Your last day of walking brings you from Pienza to Montepulciano, home to the Sangiovese Vino Nobile di Montepulciano. (Walk distance: 9 miles/14 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
  • 6 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
select 1690 490
select/first class 1990 690
first-class 2190 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).

“...more than we ever dreamed of...”

testimonial 2

When people ask how we liked our trip to Italy, we respond with…we enjoyed seeing Venice, Florence and Rome and all they had to offer but if we could only pick one place…it would be our walking tour through Tuscany! It was more than we ever dreamed of. We chose the “comfort level” for our accommodations and throughout the trip we wondered what the higher level of accommodations would be like because ours were fabulous!

It's even hard to pick which hotel was our favorite because the views and food were incredible. We were very fortunate to have another couple from Canada doing the same hikes we were so we agreed to hike together and they were the perfect fit! They made our trip even better! As we sat together in a Tuscan valley eating Pannies for lunch made by an elderly Italian lady and sipping Brunello wine we felt like we were living in a dream. We have so many wonderful memories of our hike. It was the perfect vacation! We look forward to going back for another hike through Tuscany someday but how could it get any better than what we had?

Thanks for the best vacation of our lives!

— Chuck and Esther Nobe

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.)

The hills are alive...

Tuscany walking