Discover Tuscany's "Shell of Gold"

Walking in Tuscany's Chianti

5 nights — from USD1990

Enjoy a sojourn in the heart of Chianti, away from the crowded hustle of Florence. Along little used trails and backroads, you arrive at hilltop towns with lovely views over the small wine estates and the wooded hills. Stop to sample the wines and enjoy authentic, delicious Tuscan feasts. There are castles to explore, some of them hosting highly regarded wineries, others abandoned among the forests, as well as country churches shyly hiding some remarkable art. This is the authentic Chianti which few know about: an idyllic terrain of vineyards and lush woods, sprinkled with quaint farmhouses and quiet villas.


  • Take daily walks among the Chianti vineyards
  • Visit wineries and enjoy specialty food tastings
  • Explore quaint Tuscan villages far away from the main tourist track
  • Enjoy the hearty country food of Tuscany and its spectacular wines
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At a Glance
Depart From: Florence Finish In: Florence
Starting Dates: Any day, all year long
Fitness Rating:2-4 Ratings Explained...

“...absolutely perfect...”

testimonial 1

The walking tour with Luca was superb. He was absolutely perfect, and I hope we can hike with him again someday. The hike in Volpaia was great and we had a wonderful lunch at the Castella de Volpaia. We hiked in Lamole and did a fabulous hike. He took us to the local winery there where we had a private tour in a tiny shop and even tasted the wine which would be released in October. We were definately sad to say goodbye to Luca who was our favorite part of the trip.

— Cherie and Louis Gold

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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 picks you up at your hotel and brings you into the Chianti countryside south of Florence, where you'll spend the next five nights. You take an orientation walk through the surrounding vineyards and enjoy a wine-tasting at a nearby estate.
  • Day two: You start the day with a visit to Greve, Chianti's central market town. After exploring the village's unique funnel-shaped piazza, lined with interesting shops, you walk into the hills above Greve, passing through the fortified village of Montefioralle.
  • Day three: Today you walk south of Radda to the tiny village of San Leo. In the afternoon, you visit the imposing Castello di Brolio, where the recipe for Chianti was originally invented.
  • Day four: Starting from the village of Lamole, you follow centuries-old farm tracks through chestnut woods and pastures to the summit of Monte San Michele, which at 892m is the highest point in Chianti, with wonderful panoramas of the surrounding countryside.
  • Day five: You begin the day with a walk in the area of Volpaia, a fortified village built around an 11th century castle. Your walk takes you past quaint hamlets and chapels hidden among the surrounding forests. In the afternoon, you enjoy a tasting of local specialty foods.
  • Day six: We help you on your way to your next destination with a transfer back to Florence.
Chianti 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 2390 2190 1990 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).

“...thank you for making our vacation the best...”

testimonial 2

We wanted to express our thanks to Girosole for making our vacation one of the most memorable. Luca was the most wonderful guide. His knowledge, charm, enthusiasm and connection to the roots of the beautiful area of Chianti made our daily adventures in the region special. We experienced many of the secrets in Chianti. To Girosole and Luca, thank you for making our vacation the best!

— Bob Gault and Brenda Bannerman, Sandy and Larry Warner

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.)

The Village of Volpaia

Chianti walking