Florence | Discovering the Chianti Independent Walking Tour

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A self-guided walking tour to discover the natural beauty and historic & culinary treasures of the Chianti Region. Uncover the genius behind the “Chianti Classico and Gallo Nero” wines by walking through the celebrating vineyards; follow along cypress-lined country roads & "strade bianche", past olive groves and forests of oak, beech & chestnut, and stroll through charming Tuscan villages and magnificent Renaissance cities.

Day 1: Arrive in Florence

Arrive in Florence and take a moment to breathe in the air of the Renaissance. We suggested arriving early to go for a city walk around the magnificent squares and by the illustrious Arno River. This walk starts and ends in the Piazza della Signoria and takes about 3.5 hours. Tonight enjoy accommodation at Hotel Park Palace or similar.

Day 2: Settignano to Fiesole

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 amphitheatre and Franciscan monastery. Return to your Florence hotel for a well-deserved rest. (B) 
Challenge: 3/6 hours, 8/16 km, 347/567 m ascent, 224/566 m descent

Day 3: Selection of Walks in Greve in Chianti

After breakfast, a private transfer will bring 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. Your accommodation in Greve in Chianti will be at Albergo del Chianti or similar. (B)
Walk A: Greve in Chianti loop via Uzzano
In the afternoon, make a round walk north of the attractive main square of Greve in Chianti, through a picture-perfect landscape. Starting from the main square, a round walk 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.
Challenge: 2.5 hours, 11.4 km, 425 m ascent, 447 m descent
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.
Challenge: 3.5 hours, 10 km, 358 m ascent, 355 m descent

Day 4: Panzano loop

This 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. (B)
Challenge: 4 hours, 11.7 km, 385 m ascent, 384 m descent

Day 5: From Greve in Chianti to Radda in Chianti via Monte San Michele

After breakfast, a short car transfer takes you to the highest of the Chianti hills, Monte San Michele. Hiking from Badiaccia a Montemurro 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 at a fine Enoteca, wine shop, and then continue on to Radda in Chianti where you'll spend the next two nights at Hotel Palazzo San Nicccolò, or similar. (B)
Challenge: 5/3 hours, 14/12 km, 506 m ascent, 668 m descent

Day 6: Radda in Chianti round walk

A quiet, relaxing day awaits you today. Bask under the Tuscan sun and go for a scenic walk around the old centre of Radda in Chianti. Wind along the narrow alleyways and visit the church of Santa Maria Novella. As you head out of town through the vineyard-covered slopes stop to treat yourself to a glass of Chianti Gallo Nero wine at a celebrated local vineyard. (B)
Challenge: 5 hours, 15,8 km, 586 m ascent, 585 m descent   

Day 7: Radda in Chianti to Siena

After breakfast, a private transfer will bring you to the marvellous 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. In Siena, you'll enjoy accommodation at Hotel Chiusarelli, or similar. (B)

Day 8: Arrivederci Tuscany!

The trip and our services end after breakfast, however, we highly recommend you to book extra nights in Siena to continue exploring the old centre, exquisite museums, lush galleries and marvellous churches. A visit to the top of the bell tower is also quite a sight. If you leave today for the airport, travel by local bus to Florence. (B)
   

Getting there:

Florence, Pisa and Bologna airports are flown to by both major and low-cost international carriers. All three airports can be easily reached by local transport, which is affordable and offers a frequent service. 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 20.00 Euro per day.

Optional Services:

Additional nights may be booked at any of the accommodations along the way. Airport arrival and/or departure transfers. Guided tour of Florence or Siena with a local private city guide. Cooking lessons in Florence or Siena.

Daily Departures

This Self-guided Walking Tour departs daily from April 01 to October 31, 2024
Lodging: Small comfortable 3 & 4 star hotels with a friendly, family-run atmosphere. All the rooms have private en-suite bathrooms.
THE CHALLENGE: Easy to moderate, along 'strade bianche' (small gravel roads), footpaths & mule tracks, cross small hamlets and some larger villages.

Also available as 5 day tour!