Experience a trek through Chianti

Florence to Siena Trek

5 nights — from USD2290

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.)


  • Hike a continuous 125k trail, averaging 25 km per day
  • Explore remote Chianti villages
  • Enjoy beautiful vistas across the hills of Chianti
  • Savor the great local cuisine
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At a Glance
Depart From: Florence Finish In: Siena
Starting Dates: Any day, all year long
Fitness Rating:5 Ratings Explained...

“...best hike/trip I have ever had...”

testimonial 1

The Chianti trek with Luca was the best hike/trip I have ever had. Luca was excellent. He created an incredible hike and great scenary plus he kept us going even when we were tired and hot. It was challenging but we all made it and it felt great! I am going do another trek with Luca in the Italian Alps next year! He is wonderful. Thank you.

— Joanne Coleman

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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: You begin in the Piazza della Signoria, the central piazza of Florence. From here, climbing the luxuriant Florentine hills of Arcetri, you pass through through San Donato in Collina and arrive in Troghi, where you spend your first night. (km 23 - climb total 750 m/2460 ft)
  • Day two: Continuing from Troghi, 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 find a fantastic vista on the Conca d'Oro and all the west countryside of the Chianti region. You continue to the Parco di San Michele, close to the highest point in the high hills of Chianti. (18 km - climb total 750 m/2460 ft)
  • Day four: The walk from San Michele 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.
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 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 2690 2490 2290 390
comfort/first-class 3190 2990 2790 590
deluxe 4190 3390 3790 790


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).

“...character and charm...”

testimonial 2

My husband and I absolutely loved this trip. Luca was a fabulous tour guide--humorous, knowledgeable and dependable. The best part about the trip was that we saw no other tourists while on the trails (only another group of hikers for the whole 5 days, and encountered other tourists in some of our bed & breakfasts). We definitely enjoyed taking in the Italian lifestyle: relaxed pace, wonderful food and wine, and gorgeous scenery. We thought the pace and distance was just right. Challenging enough, but not difficult to the point where it seemed impossible. The route took us through some very small towns, each with its own character and charm. We enjoyed walking through forests, hidden trails, and over mountains. The accommodations were all comfortable, clean, unique, and set in beautiful and convenient locations. Our favorites were in Bibicci and in Gaiole in Chianti. The food was wonderful. The best lunch at a restaurant was in Lamole, at Ristoro di Lamole. Our packed lunches included enough food and we did not go hungry. We loved our trip and it was extremely memorable. We would definitely recommend this trip to our friends.

— Candace and Mike

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.

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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.)

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