Discover the charm of Chianti in the heart of Tuscany. Discover the genius behind the “Chianti Classico and Gallo Nero” wines by walking through the celebrating vineyards where they are produced. Nestled amidst the flourishing art cities of Florence and Siena, the Chianti region offers natural beauty and incomparable culinary treasures such as the world famous Chianti wines and delectable homemade olive oil. Walk along cypress lined country roads and strade bianche, gravel roads, traversing forests of oak, beech and chestnut. As the Tuscan sun shines above and the golden Chianti countryside reflects your delight, you will feel as if you have stepped into a Renaissance painting.
Highlights:
♦ Florence and Siena - two of the most beautiful Italian cities
♦ The wine hills of Greve and Radda, wonderful landscapes and medieval villages
♦ Superb culinary specialties, including great salami, Florentine steak and outstanding wines
Itinerary:
Day 1. Florence
Arrival to Florence on your own. Take your time to explore the magnificent squares and Renaissance buildings. Overnight in Florence.
Day 2. Florence - Settignano - Fiesole - Florence
Travel uphill on a twenty-five minute local city bus ride to the village of Settignano where the walk begins. On the walk, you have magnificent views of cypress trees, olive groves, Renaissance villas and the whole city of Florence at your feet. Stroll through the charming town of Fiesole and tour its Etruscan ruins, Roman amphitheater and Franciscan monastery. Overnight in Florence.
Walking distance: 8 km; 3 hrs; ascent/descent: +347/-224m - (longer option: 6 hrs.; 16 km; ascent/descent: +567/-566m)
Day 3. Florence - Greve in Chianti
After breakfast, a private transfer will drive you to Greve in Chianti, a rustic market village and the capital of the Chianti wine producing region. Check in to the hotel and head over to Le Cantine di Greve where you can taste over 50 different Chianti wines. Take advantage of the daylight to walk around this gorgeous scenery by choosing between two routes:
Walk A: Greve in Chianti loop via Uzzano
Make a round walk north of the attractive main square of Greve in Chianti, through a picture perfect landscape. From the main square a round walk starts and takes you through the Chianti Classico area passing by the Villa Calcinaia and numerous vineyards with “aziende agricole” (farms) where the prestigious Chianti wine is produced.
Walking distance: 9 km; 3 hrs.; ascent/descent: +225/-225m.
Walk B: Greve loop via Montefioralle
Explore the wonderful surroundings through the forest, among dense wild vegetation, villas, vineyards and olive groves. You will be passing by abandoned old farms, ruins and beautiful villas before reaching the panoramic hamlet of Montefioralle.
Walking distance: 10 km; 3,5 hrs.; ascent/descent: +360/-355m.
Day 4. Greve in Chianti (Panzano loop)
The walk is made up of a loop out of Panzano. You walk through the hills surrounding the village, in the classic Chianti landscape that alternates forests with vineyards, offering you the possibility to discover ancient Roman farmsteads.
Walking distance: 11,7 km; 4 hrs; ascent/descent: +385 /-385m.
Day 5. Greve in Chianti - Radda in Chianti
After breakfast, a short car transfer takes you to the highest of the Chianti hills, Monte San Michele. From Badiaccia you descend through a forested valley of century old chestnut trees and continue towards the stunning medieval hamlet of Volpaia, situated amongst vineyards and castles. Stop in for a glass of red wine at a fine Enoteca, wine shop, and then continue on to Radda in Chianti.
Walking distance: 12-14 km; 3-5 hrs; ascent/descent: + 506 /-668 m.
Day 6. Radda in Chianti
A scenic walk around the old centre of Radda in Chianti. Stop for lunch in the lovely hamlet of Vertine and in the afternoon treat yourself to a glass of Chianti wine at Colle Bereto, a celebrated local vineyard that you encounter along the way back to Radda.
Walking distance: 15,8 km; 5 hrs; ascent/descent: +586 /-586 m.
Day 7. Radda in Chianti - Siena
After breakfast, a private transfer will lead you to the marvelous city of Siena, famous for its biannual “Palio” horse race, held in the most beautiful shell-shaped square in Europe: the Piazza del Campo. Don’t miss a visit to the Duomo, an architectural treasure, and numerous imposing medieval palaces. History comes alive as you meander through the narrow streets of this fantastically preserved jewel of Italy.
Day 8. Departure
After breakfast departure on your own or extra days in Siena.
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PRACTICAL INFORMATION:
- Transport to Florence, Pisa and Bologna airports are flown to by both major and low cost international carriers. From Florence airport take the direct local bus to downtown. From Pisa airport, you can take either a direct train or bus to Florence. From Bologna airport take the bus to Bologna central station, then the train to Florence. To return from Siena to Florence, the SITA-TRA.IN bus station is very close to the hotel and a bus leaves every 30 minutes.If you come with your own car, please note that the hotels we use in Florence and Siena do not have a private parking lot of their own, there are several guarded parking areas which cost approximately €20 per day.
- Tourist tax/city tax “tassa di soggiorno” to be paid in cash on the spot in the cities of this tour (it varies depending on the city and on the hotel’s category)
- Walking in Chianti: The walks are generally easy and are along small gravel roads (strade bianche), footpaths and mule tracks on hilly terrain. You will cross several small hamlets and some larger villages.
- Luggage transfer: You travel with your luggage from from Florence to Greve in Chianti (on day 3), from Greve in Chianti to Badiaccia on Monte San Michele (start of the walk on day 5)-the luggage to Radda and from Radda in Chianti to Siena (on day 7). Included 1 bag per person. Bags with your name and a note with the name of the next accommodation should be ready at the reception or store room by 9:00 in the morning.
- Wine & dine: There are plenty of opportunities to taste both the outstanding local cuisine and a wide array of prestigious regional wines.
- Radda: Our Affittacamere/guest house in Radda will provide you with a voucher for breakfast in a local bar
- Necessary equipment: sturdy walking boots and walking socks, a small rucksack, a water bottle with at least 1 litre capacity, sunglasses, sunhat, sun cream, rainwear and insect repellent.
Price Includes: 7 overnights in a shared double room with private bathroom and breakfast at standart hotels and guest houses
Transfers as per program
Luggage transfer from Florence to Greve in Chianti,from Greve to Radda and from Radda to Siena
Map and road book in English (1 copy per booking)
24-hour telephone service
Not Included: Flight or other transport to first accommodation in Florence and the last accommodation in Siena
Transfers and other transport by public bus not mentioned included
Drinks and meals not mentioned in the program
City tax - totally about 22 EURpp paid on spot
Entrance fees & wine tastings
Personal expenses
Additional nights in Florence and Siena
Insurance
Extra Services: Solo Traveller Supplement (2026): 260 EUR - paid on top of the single supplement
Extra nights/transfers/ additional program before/after the tour – please ask for our best quote
The tour can be organised as a 5-day/4-night program: contact us for a price
