Discover Tuscany's "Shell of Gold"

Walking in Tuscany's Chianti

5 nights — from USD2190

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.

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.

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.