Explore the trails from village to village

Walking among Tuscany's Hilltowns

5 nights — from USD2190

This tour combines the best of two regions, both famous for their wines and classic Tuscan landscapes: Chianti and the Val d’Orcia. In Chianti, you concentrate on the area around Panzano and Greve. Panzano is located at the heart of the Conca d’Oro, where much of the finest wine is produced. Moving south to the Val d’Orcia, you visit the hilltown of Montalcino, famous for its precious Brunello wine, arguably the most prized of Italy’s fine wines. You also explore Pienza, a perfect little gem of a Renaissance town, and Montepulciano, producer of another of Italy’s great 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: Your guide picks you up in Florence and brings you into Chianti to the town of Greve. After exploring the town, you take a walk in the hills above Greve, passing ancient villages, fortified towns and quaint country churches.
  • Day two: Starting from the castle of Volpaia, you walk to Querce della Fanciulla, for a wonderful panorama across the Chianti landscape. In the afternoon, you visit the Castello d’Albola for a private tour and wine-tasting as well as the picturesque village of Radda nearby.
  • Day three: Today’s walk brings you to the highest point in Chianti and through the tiny mountain villages of Casole Alta and Le Masse. Afterwards, you visit nearby Siena, for a walk through its medieval neighborhoods, finishing the day in Pienza where you spend the next three nights.
  • Day four: You walk today from Montalcino to the Abbey of Sant’Antimo, a 12th century jewel fashioned in large part of luminous alabaster. In the afternoon you enjoy a wine-tasting of Montalcino’s famous Brunello wine.
  • Day five: Starting from the Renaissance village of Pienza, you walk to Montepulciano, known for another fine wine, the Vino Nobile di Montepulciano.
  • Day six: We help you on your way to your next destination with a transfer to Chiusi on the main Rome-Florence railway.

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 2590 2390 2190 410
select 2820 2650 2450 620
first class 3770 3560 3350 720
deluxe 4820 4650 4430 1040

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.