Explore the trails from village to village

Walking among Tuscany's Hilltowns

5 nights — from USD2090

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.


  • Take daily walks among the Tuscan hilltowns and vineyards
  • Visit wineries and olive oil producers with personal tours
  • Explore quaint Tuscan villages
  • Enjoy the hearty food of Tuscany and its outstanding wines
Get The Full Tour Details
At a Glance
Depart From: Florence or Siena Finish In: Florence or Siena
Starting Dates: Any day, all year long
Fitness Rating:1-4 Ratings Explained...

“...wonderful and memorable experience...”

testimonial 1

A truly wonderful and memorable experience! Luca was not only very knowledgeable and good company; he was always prepared to go the extra mile and nothing was too much trouble for him. We felt thoroughly spoilt. Thank you so much for all your efforts on our behalf. It really was a pleasure dealing with Girosole. Just as an aside: perhaps you should suggest that clients allow for A LOT of extra baggage space for pecorini cheese, paneforte, chianti classico vino, shoes and handbags!!!!!

— Ann, Tarryn, Hilary, Karen and Junette

Get The Full Tour Details

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.
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 4590 4390 4190 990


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).

“...everything we had hoped for...”

testimonial 2

I wanted to send you a note and express my thanks for a wonderful trip! The whole experience was absolutely fabulous! The itinerary you arranged for us was everything we had hoped for, visiting wonderful wineries and walking through the hills of Tuscany. Francesca was a terrific guide. She has a wonderful sense of humor combined with unlimited knowledge of Italian history, culture, architecture and plants and animals. Please send our regards to Girosole for a memorable experience.

— Rosemary Spitzer, Sheila Fetner, Valerie W. Edson, Addison Ore

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.

Get The Full Tour Details

1 Contact Info (* required)
2 Travel Info (optional)

(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.)

Across the Val d'Orcia

Tuscany walking