Discovering the Chianti Region in Tuscany, Italy

Discovering the Chianti Region in Tuscany, Italy

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. 

Tour 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 


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: 8-16 km; 3-6 hrs 

Day 3. Florence - Greve in Chianti
After breakfast, take the local bus (with your luggage) or book a private transfer to Greve in Chianti, a rustic market village and the capital of the Chianti wine producing region. Check in to the hotel and if you would like 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: 11,4 km; 2,5 hrs

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

Day 4. Greve in Chianti (Panzano loop)
Greve in Chianti offers a lot of different pearls that you can discover. By the local bus to Panzano.
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. Take the local bus back to Greve.
Walking distance: 11,7 km; 4 hrs

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: 9,5 km; 3 hrs

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: 15,7 km; 5 hrs

Day 7. Radda in Chianti - Siena
After breakfast, take the local bus (with your luggage) or with a prearranged private transfer, 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.

Practical information: ►You can fly to Rome, Florence or Pisa. From Rome and Pisa there are regular trains to Florence (check ►There is a 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) ►We can organise cooking lessons for you in Florence and Siena as well as guided tours of these cities with a local guide ►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 ► There are plenty of opportunities to taste both the outstanding local cuisine and a wide array of prestigious regional wines. ► During high season it is possible that you might sleep in different accommodation to the ones that the tour is based on but of same quality and standard. This might affect a bit your route ►We can organise this tour for one person only as well: contact us for a price.

Recommended travel period of the year: April - October

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 a guesthouse in Radda
luggage transfer from Florence to Greve in Chianti and from Radda to Siena and private transfer from Greve to Monte San Michele / Badiaccia Montemuro on day 5 at 9:00
24-hour telephone service
map and road book in English

Not Included:
flight tickets
personal insurance
transfer from/to airport and other transfers / transport by public bus
drinks and meals not mentioned in the program
city tax where required
personal expenses
additional nights in Florence and Siena
entrance fees

Additional Services:
Single room supplement (depending on the period of travelling): 01/04-28/05 + 9/7-28/8: 235 EUR; 29/05-8/07 + 01/10 - 31/10: 240 EUR; 29/8 - 30/9: 220 EUR;
Solo supplement depends on the period of travelling. Contact us for more information.
The tour can be organised with accommodation at 3*** and 4**** hotel some with swimming pools - contact us for prices and information
the tour can be organised as a 5-day/4-night program: contact us for a price

Vacation Extensions:
Medieval Umbria - From Assisi to Spoleto


Discovering the Chianti Region in Tuscany, Italy (Rated 4.72 / 5 Based on 282 Reviews.)

No special experience is needed; everyone who is in condition to cope with long Saturday walks in the forest can also cope with these tours. As a rule, the trips are short and at a low altitude. Often, it is your choice to join or skip a day-tour. The routes follow a hilly terrain without steep ascents and descents. Normally we walk 3/5h a day.

Group Size
Min. 1 person
Reservation System Code
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