Vineyards and forests between Florence and Siena

Self-Guided Walking in Chianti

6 nights — from USD1460

From the gateway to Chianti into the heart of Chianti Classico: our self-guided Chianti walk takes you through world-famous vineyards, picturesque olive groves, lush forests and some of the most important towns that grace the Chianti landscape. Famous for its world-class wine today, the territory between Greve and Radda was once the battleground for the rival cities of Florence and Siena. You’ll walk to the towns of Greve, Panzano and Radda while exploring the hilltop hamlets, fortified villages, ancient castles and little chapels that lie between. And throughout your holiday, we provide you with all the tools and support you need to help you put your spirit of adventure into action.

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: We pick you up in Florence and bring you into the heart of Chianti. Once here, you start your walk from the village of La Panca and walk through lush forest with marvelous views from the many clearings. You arrive in Greve, notable for its triangular-shaped square and its many markets throughout the year. You spend your first two nights here.
  • Day two: You take a ring walk through the rolling hills west of Greve to enjoy the area’s picturesque landscape and rich history. One of the highlights is the fortified village of Montefioralle, featuring some of the best-preserved architecture in the area.
  • Day three: From Greve you walk south along peaceful country roads through rolling vineyards and olive groves. Later, you finish the walk in Panzano, halfway between Florence and Siena and long a point of conflict between the two city-states. Here you spend your next two nights.
  • Day four: Today’s ring walk takes you through through the hills southeast of Panzano. Along the way, you pass through Lucarelli, a hilltop hamlet enclosed by forest and vineyards. You’ll also enjoy stunning views over a natural haven adorned by secluded stone houses.
  • Day five: You begin the day with a walk from Volpaia, a fortified village built around an 11th century castle. From here, you pass quaint hamlets and chapels hidden among the surrounding forests. You arrive in Radda, headquarters of the Chianti League, where you spend your final two nights.
  • Day six: On today’s final ring walk you climb towards Valimaggio. Here you’ll discover cypress-framed alleys, vineyards, and endless views across Tuscany. You’ll also enjoy a memorable finish to an unforgettable holiday in one of Italy’s most beautiful countrysides.
  • Day seven: 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.

  • 6 nights accommodation with en-suite facilities
  • 6 days of walking
  • breakfast each day
  • GPS app with walk coordinates and emergency contact
  • detailed maps and route descriptions
  • a descriptive guide of the various sites to see
  • a Tour Rep to oversee your tour and move your luggage each day
  • 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. You can keep your tour private to your own group or you can open your tour for other travelers to join. Single Supplements (sing. supp.) are charged on single occupancy rooms only. All prices are quoted per person in USD.

accomm. level 2+ p sing. supp.
comfort 1460 410
select 1780 510
first class 2290 720

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).

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.