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Tourist walking among vinyards
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Tuscany Discovering the Chianti
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Duration :
8 days
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Apr May Jun Jul Aug Sep Oct
price in double room from: € 653
Tuscany Discovering the Chianti

Tuscany Discovering the Chianti

A land of culture, wine and olive oil

  • Florence, cradle of the Renaissance and Medieval Siena with the imposing Piazza del Campo
  • Fiesole and the Ancient Roman amphitheatre
  • The wine hills of Greve in Chianti and Radda in Chianti
  • Great wineries to visit and wines to taste
  • Wonderful landscapes, medieval villages and hamlets
  • Friendly people, great salami, Florentine steak, Cantucci with vinsanto and of course … wine!
Map walking routes the Chianti
View map

The walks are along small gravel roads (strade bianche), footpaths and mule tracks on hilly terrain. You will cross several small hamlets and some larger villages.

Start: Florence                  Finish: Siena

Day 1: Arrive in Florence
Day 2: Walk from Settignano to Fiesole (8 km, 16 km)
Day 3: Selection of walks in Greve in Chianti (11.4 km, 10 km)
Day 4: Panzano loop (11.7 km)
Day 5: Transfer to Monte San Michele and walk to Radda in Chianti (14 km, 12 km)
Day 6: Radda in Chianti round walk (15.8 km)
Day 7: Travel to Siena
Day 8: Arrivederci Tuscany!

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.


Day 2:    Walk from Settignano to Fiesole (8 km, 16 km)

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.

Challenge: 3/6 hours, 8/16 km, 347/567m ascent, 224/566m descent


Day 3:    Selection of walks in Greve in Chianti (11.4 km, 10 km)

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 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

In the afternoon, 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.

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: 2.5/3.5 hours, 11.4/10 km, 425/358m ascent, 447/355m descent


Day 4:    Panzano loop (11.7 km)

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.

Challenge: 4 hours, 11.7 km, 385m ascent, 384m descent


Day 5:    Transfer to Monte San Michele and walk to Radda in Chianti (14 km, 12 km)

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 at a fine Enoteca, wine shop, and then continue on to Radda in Chianti.

Challenge: 5/3 hours, 14/12 km, 506m ascent, 668m descent


Day 6:    Radda in Chianti round walk (15.8 km)

A quiet, relaxing day awaits you. 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 vineyards.

Challenge: 5 hours, 15.8 km, 586m ascent, 586m descent


Day 7:    Travel to 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:    Arrivederci Tuscany!

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 marvelous churches. A visit to the top of the bell tower is also quite a sight. 


'standard' hotels

All accomodations are carefully selected because of their location, atmosphere and/or unique services. All rooms are en-suite.

You can find below the standard hotels of this trip. If a hotel is fully booked, then we will book a similar one for you and inform you about the alternative booked. 

Extra overnight: You can book additional night(s) at any of the accommodations along the way.

This tour can be booked in upgraded hotels.

Hotel Malaspina (Firenze)
Hotel Malaspina *** (Firenze)

Hotel Malaspina is centrally located in Florence a few steps from Piazza Duomo and train station housed in a 19th century building. Rooms are well finished with wooden furniture in classic Tuscan style like the Florentina terra cotta tile floors. They have free Wi-Fi, private bathroom, telephone, TV, mini-bar, air conditioning. Buffet breakfast offers typical Florentine sweet pastries and savory food.

Albergo Casa al Sole (Greve in Chianti)
Albergo Casa al Sole *** (Greve in Chianti)

Situated in a great location in Greve in Chianti, this hotel has a slightly dated but comfortable and clean rooms with TV, free Wi-Fi and private bathroom. Some of these have a balcony or terrace. Staff is very kind. Breakfast is good and rich.

Affittacamere Giovannino (Radda in Chianti)
Affittacamere Giovannino (Radda in Chianti)

This Guesthouse is very informal and simple and at the ground floor there is its restaurant very recommended. Rooms are simple and well-finished with private bathroom. Owners are courteous and welcoming. Breakfast is international and good.

Hotel Cannon d'Oro (Siena)
Hotel Cannon d'Oro (Siena)

Hotel is centrally located in Siena, near Piazza del Campo and the building dates to the early eighteenth century and is a building originally owned by the noble Bulgarini family. Rooms are simple and clean without air conditioning. Wi-Fi doesn't work very well. Breakfast is normal. Staff courteous and welcoming.

'Select' hotels
Hotel Park Palace**** (Firenze)
Hotel Park Palace**** (Firenze)
Albergo del Chianti (Greve in Chianti)
Albergo del Chianti*** (Greve in Chianti)
Hotel Palazzo San Niccolò ****(Radda di Chianti)
Hotel Palazzo San Niccolò ****(Radda di Chianti)
Hotel Chiusarelli ***(Siena)
Hotel Chiusarelli ***(Siena)
practical info

You can start on any day of the week, subject to availability, between April and October.

Florence (FLR), Pisa (PSA) and Bologna (BLQ) airports are flown to by both major and low cost international carriers. All three airports can be easily reached by local transport.

Arrival in Florence

From Florence airport (FLR), take the direct local bus to downtown.

From Pisa airport (PSA), you can take either a direct train or bus to Florence.

From Bologna airport (BLQ), take the bus to Bologna central station, then the train to Florence.

Departure from Siena

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. From Florence, you can reach both Pisa and Bologna by train.

Check train and timetables on: (train) (bus)

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 Euro 20 per day.

GPS tracks are available on request.



  • 7 Nights in selected B&Bs, hotels and agriturismo
  • 7 Breakfasts
  • Private transfer (+ luggage) from Florence to Greve in Chianti on DAY 3
  • Private transfer from Greve in Chianti to Badiaccia + luggage to Radda in Chianti on DAY 5
  • Private transfer (+ luggage) from Radda in Chianti to Siena on DAY 7
  • Detailed information pack, route notes and maps with tracks on
  • 24/7 telephone support 

Not included

  • Travel insurance
  • Travel to Florence and from Siena
  • Trains and busses wherever necessary
  • Lunches & Dinners
  • Drinks and snacks
  • Personal equipment
  • Tourist taxes


  • Additional nights before, during or after the walk
  • Single Room Supplement(s)
  • Solo Traveller Supplement
  • Transfer from airport to Florence
  • Transfer from Siena to airport

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'Standard' hotels 'Select' hotels
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