Walk through classic Tuscan landscapes

Walking in Tuscany's Val d'Orcia

5 nights — from USD2090

This is Tuscany in style – splendid days spent rambling through a serene landscape of vineyard-draped hills, cypress-lined paths and silvery groves of olive trees. Visit the pretty hilltop town of Montalcino, famous for its precious Brunello wine, arguably the most prized of Italy's fine wines. Nearby is the Abbey of Sant'Antimo, where you can hear the monks singing their vespers. You can also explore Pienza, a perfect little gem of a Renaissance town, and Montepulciano, producer of another of Italy's great wines – all the while savoring much great, wholehearted Tuscan cuisine.


  • Take daily walks in the countryside of Southern Tuscany
  • Explore the towns of Montalcino, Pienza and Montepulciano
  • Taste the famous Brunello wine at a private wine-tasting
  • Enjoy Tuscan specialties and cuisine
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At a Glance
Depart From: Florence or Siena Finish In: Chiusi
Starting Dates: Any day, all year long
Fitness Rating:1-4 Ratings Explained...

“...more than met our expectations...”

testimonial 1

Our experience with Girosole more than met our expectations. Both Michelangelo and Francesca were wonderful guides and their services truly enhanced our experience. The accommodations were delightful, the days spent in ways that we had hoped for, and the food most memorable. The service provided by you prior to the trip and the activities while in Italy have served to make us suggest Girosole as a tour agent of choice to several people, and we will continue to extol your praises. Here's a picture taken while we were with Francesca in Panzano at that Wine Festival. This was after a 10 km walk, most enjoyable. We actually enjoyed some Vinsanto with biscotti as a late evening 'snack' with some friends last night — a reminder of Italy and the love of good food that one finds there. Again, my thanks for your attention from our first inquiry through our touring overseas!

— Jon and Linda Lambert

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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: Your guide meets you in Florence or Siena and brings you to Montalcino, famous for its fine Brunello wine. Along the way you stop at the abbey of Monte Oliveto Maggiore, which boasts a beautiful cycle of frescoes in its main chloister.
  • Day two: Today features a guided walk to the Abbey of Sant'Antimo, a 12th century jewel fashioned in large part of luminous alabaster. Afterwards, you enjoy a comparison tasting of Brunello, Montalcino's famous wine.
  • Day three: Today, you walk in the area of Bagno Vignoni, a village built around thermal springs in use since Roman times. Later, you visit the citta fortificata ("fortified city) of Radicofani.
  • Day four: Your walk today brings you to the Renaissance village of Pienza to learn about the Pope who tried to make this, his hometown, into a perfect expression of Renaissance form.
  • Day five: Your destination today is Montepulciano, known for another fine wine, the Vino Nobile di Montepulciano. You explore the vintners' cellars, dug deep beneath the town's medieval quarter among ancient Etruscan tombs.
  • Day six: 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.

  • 5 nights accommodation with en-suite facilities
  • breakfast each day
  • 2 dinners
  • full-time, professional Tour Leader
  • guided walks each day
  • specialty foods tastings
  • paid entrance to all included activities
  • all land transfers to and from tour area, and during tour
  • 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 2-3 p 4-5 p 6+ p sing. supp.
comfort 2490 2290 2090 390
select 2690 2490 2290 590
first class 3590 3390 3190 690
deluxe 4790 4590 4390 890


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).

“...thoroughly enjoyable...”

testimonial 2

Having been to Tuscany a few years ago I was really looking forward to coming back. However nothing prepared me for the "heavenly-ness" of Tuscany's Val d'Orcia which could only be fully appreciated by walking through it!! The walks were all well within our capabilities and thoroughly enjoyable. The destinations to monasteries, churches, winery/wine tastings, small villages, thermal springs, etc. were all well thought out, and unique experiences. We loved them all. Thank you Luciano, Peter, Giuseppe and Luca!!! Thank you again for arranging this lovely holiday. We would not hesitate in recommending Girosole to any of our other friends!!

— Joanna (Giovanna) MacDonald

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.)

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