Experience a trek through Chianti

Florence to Siena Trek

5 nights — from USD2450

Imagine walking every step of the way from the Piazza della Signoria in Florence to the Piazza del Campo of Siena. If you’re into true trekking, this hike’s for you (if you’re not, we have other gentler walks). This tour is a challenge, averaging 20-25 km per day of very hilly terrain. Along the way, you’ll traverse the wine-growing region of Chianti, with panoramic vistas across vineyards and olive groves. You’ll walk through deep chestnut woods and forests of centuries-old oaks. You’ll pass mystic chapels and medieval villages, along unknown Etruscan paths and ancient Roman roads. (Guided trip only – no self-guided option.)

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: You begin in the Piazza della Signoria, the central piazza of Florence. From here, climbing the luxuriant Florentine hills of Arcetri, you pass through the Chianti countryside and arrive in Impruneta, where you spend your first night. (km 15 – climb total 750 m/2460 ft)
  • Day two: Continuing from Impruneta, you walk through chestnut and oak forests, following an ancient Etruscan path and an important Roman commercial road. You finish the day in the most important wine market of Chianti, Greve, which is also the capital of the Chianti region. (27 km – climb total 900 m/2950 ft)
  • Day three: From Greve you walk to the mountain village of Lamole, where you enjoy a fantastic vista over the Conca d’Oro. You continue to Radda where you spend the night. (18 km – climb total 750 m/2460 ft)
  • Day four: The walk from Radda brings you through the Natural Park of Cavriglia, one of the most interesting wilderness areas of the Chianti region. You finish your walk near the impressive Castello di Brolio, where the recipe of Chianti Classico originated. (26 km – climb total 500 m/1640 ft)
  • Day five: The hike today takes you through the Etruscan place of San Giusto a Rentennano, now a winery. Along the path, it is possible to see the towers of Siena, your final destination. After passing through Montaperti and the Castello delle Quattro Torri, you enter Siena through its medieval gates, finishing finally in Piazza del Campo, Siena’s central piazza. (25 km – climb total 250 m/820 ft)
  • Day six: After a morning free to visit Siena, you are ready to depart for your next destination.

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 hikes each day
  • daily luggage transfers during the 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 2820 2630 2450 410
comfort/first-class 3350 3140 2930 620
deluxe 4390 4190 3980 830

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.