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Self-Guided Walking in Tuscany

Enjoy a self-guided adventure from inn to inn

tour pic

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.

Highlights

  • 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

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: 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. You return to Montalcino for a second night. (Walk distance: 7 miles/11 km - climb total: 450 ft/150 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: 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
  • 6 days of walking
  • breakfast each day
  • detailed maps and route descriptions
  • a descriptive guide of the various sites to see
  • a cell phone for emergencies
  • a Tour Rep to oversee your tour and move your luggage each day
  • all taxes and service charges at hotels
  • 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.)

Pricing

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. All prices are quoted per person in USD.

accomm. level 2+ p sing. supp.
comfort 1390 390
comfort/select 1690 590
select/first-class 1990 690

Scheduling

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.

Contact Information (* required)

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Travel Information (optional)

Accommodation preference (check all that apply):

  Comfort

  Select

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  Open to other travelers to join

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At A Glance

Tuscany Self-Guided Walk

8 days / 7 nights

From USD1390

Depart From:

Siena

Finish In:

Chiusi

Starting Dates

Any day of the week, all year long

Fitness Rating:

2-3

“...truly a special experience...”

tuscany

Julia and I had a wonderful time. We are still talking daily about our experiences. All of the hotels were nice and the people were friendly. Whenever we announced that we were with Girosole, people smiled and were especially helpful to us. The suggested restaurants were very good and we had some wonderful discoveries on their menus. This was truly a special experience for us for a special occasion in our lives. Thank you so much for putting together such a nice tour at an affordable price.

Dennis and Julia Crowley

Where in the world? (zoom out for the big picture)


“...wonderful thanks to you...”

tuscany

Our trip was wonderful thanks to you. The accommodations and restaurants that you arranged were very good. The restaurants were usually the best in the area and not 'touristy'. The directions were excellent and the walks beautiful. The people were very friendly and helpful and I found that my limited Italian did help in some areas. We loved all the restaurants and the accommodations were clean and perfect for us. I felt that this walk was well organised, from pick up to drop off, documentation was very good and the cell phone an added comfort.

Liz Nicolosi

The hills are alive...

tuscany

Quality You Can Trust

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