italy walking tours

Self-Guided Hiking in Tuscany

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 (like Pienza, Montalcino and Montepulciano) and for its breathtaking landscapes. The full 8 day tour covers a continuous trail, with a new leg each day, setting out from the 13th C. monastery of Monte Oliveto Maggiore to finish 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.

Highlights

  • 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
Tuscany self-guided hiking tour

Itinerary Outline

Here is an outline of a suggested daily itinerary. You can shorten or lengthen this tour to fit your travel dates. Request a detailed itinerary using the contact form below:

What's Included

(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 490
comfort/select 1690 590

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)

Would you like us to call you?

  No, contact by email is fine for now

  Yes, I would like to speak to a Travel Consultant

Travel Information (optional)

Accommodation preference (check all that apply):

  Comfort

  Select

  First Class

  Deluxe

Would you prefer a tour which is (check both if fine either way):

  Open to other travelers to join

  Private to my own group

We do not share your info with anyone (view our Privacy Policy).

Tour at a Glance

Tuscany Self-Guided Hiking
8 days / 7 nights
from USD1390

Personalize this tour to your travel dates, budget, accommodations, activity level and interests

Departing from:

Buonconvento

Finishing in:

Chiusi

Starting dates:

Any day of the week, all year long

Fitness rating:

3-4

(ratings explained .. )


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

Tuscany trip review

BBB OnLine Reliability Seal

Girosole - carbon balanced with TerraPass

Adventure Travel Trade Association