Self-Guided Walking in Tuscany
7 nights — from USD1460
Due to the myriad uncertainties created by the COVID-19 pandemic, we have changed our booking and cancellation policies to a USD50 per person deposit with cancellation and full refund until 31 days before departure. Read more here.
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
Depart From: Siena
Finish In: Chiusi
Starting Dates: Any day, all year long
Fitness Rating: 2-3 (Ratings Explained)
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!
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: 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 miles/13 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: 1490 ft/460 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.
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
- 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.)
“...more than we ever dreamed of...”
When people ask how we liked our trip to Italy, we respond withâ€¦we enjoyed seeing Venice, Florence and Rome and all they had to offer but if we could only pick one placeâ€¦it would be our walking tour through Tuscany! It was more than we ever dreamed of. We chose the â€œcomfort levelâ€ 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
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.
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).
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.