Walking the Val d’Orcia

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  • No booking fees
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5.0 Based on 1 Review
  • duration 7 days
  • tour type Private
  • tour_type Private tour
  • age requirement 18+ years old
  • age_requirement 18+ years old
  • guiding method Self guided/Independent
  • Starts Siena, Italy
  • Ends Montepulciano, Italy
  • Follow the traces of the ancient Via Francigena
  • Fully immerse yourself in the worldfamed Tuscan landscape
  • Visit Montepulciano, Bagno Vignoni and Pienza
  • Spend your days walking the landscape and exploring the towns and attractions
This self-guided walking tour is a perfect introduction to the region of Tuscany. The tour threads together some of the most attractive towns and villages in Tuscany in an eloquent procession, although the focus of this tour is on appreciating the beautiful Tuscan countryside and landscapes. For people who love museums, galleries and gothic and Romanesque architecture, there is plenty to see and do.

In combination with walking through the area, you will have plenty of time to visit attractions on most of the days. You also have the time to visit the historic towns of San Gimignano, Colle Val D’Elsa, Siena and Montepulciano, and of course all the beautiful medieval villages along the Via Francigena and in the Val d’Orciaas including Monteriggioni, admired by Dante in his Divine Comedy, San Quirico, Buonconvento, Bagno Vignoni and Pienza, arguably the most perfect Renaissance town in Tuscany.

The emphasis of the tour is to enjoy the countryside, the rolling vineyards, the poppies in spring and the wild cyclamen in autumn. Most of all, many of the views have barely changed for hundreds of years. South of Siena, you head off into a picturesque Tuscan landscape of gentle hills, crowned with a lonely pine or oak tree, while cypresses line the way towards distant farmhouses.

At first you walk mainly through forests and vineyards, then through the spectacular rolling hills of the Crete Senesi, with its extensive fields of wheat and sunflowers, and finally, the rolling hills of the Val d’Orcia, scattered with picturesque little towns. Walking here is an unforgettable experience!

You come across one of the most beautiful abbeys in Tuscany at Monte Oliveto Maggiore. This is a typical red-brick monastery where friars of the Benedictine Order still worship. The next historical villages are Buonconvento and Montalcino, surrounded by vineyards of San Giovese grapes, for the famous Brunello wine. Then you enter the Val d’Orcia, a unique landscape scattered with wonderful little towns, such as San Quirico, Pienza and Bagno Vignoni, with its unique town square (a huge pool of healthy sulphurous water!). Your tour finishes in the town of Montepulciano where medieval architecture and vineyards fill the landscape.
5 - Excellent
Based on 1 review
Amazing trip
5 - Excellent
  • Britta Schmidt
  • From Germany
  • On Jul 02 2018
“The colors, the wine, the silent walks, the calm little villages where time stopped. Couldnt imagine a better holiday. Thank you all Genius Loci Travel”
  • Day 1: Arrival
  • Day 2: Asciano
  • Day 3: Through Chiusure to Buonconvento
  • Day 4: Along the Orcia to Bagno Vignoni thermal baths
  • Day 5: Through the archetypal Tuscan landscape to Pienza
  • Day 6: Vineyards, olive groves and rolling hills
  • Day 7: End of tour
  • 6 breakfasts and 1 dinner
  • Accommodation: 1 night in Siena, 1 night in Monte Oliveto, 2 nights in San Quirico d’Orcia, 2 nights in Montepulciano
  • Extensive route notes, with description of the route & tourist information
  • Maps at 1 : 25.000 scale
  • 24/7 assistance
  • Luggage transport
  • Private transfers as specified
OPTIONAL ADDONS (Available during check-out)
  • Single supplement
  • Departure taxes
  • Visas
  • Travel Insurance
  • Drinks and meals not mentioned in the itinerary
  • Optional additional tours or activities
  • Tips
  • Items of personal nature
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20% Deposit payable upfront. Remaining balance payable 45 days prior to trip departure. Free cancellation up to 45 days prior departure, but the 20% deposit paid is non-refundable. No refund applicable within 45 days of departure.


A deposit of 20% is required when booking this tour. The remaining balance will be charged 45 days prior departure. For any bookings within 45 days of departure, the full tour amount will be charged upon booking.

Travel Insurance

We advise to take out Travel Insurance to cover for any unforeseen circumstances. Bookmundi recommends World Nomads' travel insurance.

Other Practical InformationLevel of difficulty: Moderately easy. Mostly easy walks, though some include walking uphill, sometimes on paths with rough surfaces. On some days extensions or shortcuts are possible. Fitness: A high standard of fitness is not necessary but you should be able to walk for up to 5 hours a day in hot sun on dusty or stony tracks. During summer the difficulty of this tour definitely increases due to the heat. We therefore advise against booking this tour during the period between about 14th July and 20th August. Footpaths: Most paths are relatively well maintained; on many occasions you’ll follow socalled strade bianche (unsurfaced roads), easy to follow and very unlikely to be overgrown (we continuously check our routes – please help us by providing your feedback on the quality of the paths). Waymarking: A large part of the route is waymarked, but at certain places we have found more interesting routes than the waymarked ones; therefore, you should follow the route descriptions provided together with the maps. With these, you will always be able to find your route.
If you have any question about this tour or need help with planning a trip, please do not hesitate to get in touch with us. We're ready to help.
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