Walk through classic Tuscan landscapes

Walking in Tuscany's Val d'Orcia

5 nights — from USD2190

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, made in large part of alabaster that glows with an inner light. 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.

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.

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 5030 4820 4650 930

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.