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Tourist walking among vinyards
Find your perfect trip!
Find your perfect trip!
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: € 805
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 its imposing Piazza del Campo
  • Fiesole and the ancient Roman amphitheatre
  • Chianti wine hills in Greve and Radda
  • Great wineries to visit, great wines to taste
  • Friendly locals, tasty salami, Steak Florentine, Cantucci with vinsanto and of course … wine!
Map walking routes the Chianti
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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 - 16 km / 5 - 10 mi)
Day 3: Selection of walks in Greve in Chianti (11.4 -10 km / 7 - 6 mi)
Day 4: Panzano loop (11.7 km / 7,5 mi)
Day 5: Transfer to Monte San Michele and walk to Radda in Chianti (14 km / 8 mi)
Day 6: Radda in Chianti round walk (15.8 km / 10 mi)
Day 7: Travel to Siena
Day 8: Arrivederci Tuscany!

Day 1:    Arrive in Florence

Arrive in Florence and instantly begin to take in the vibrant atmosphere of the Renaissance. Plan to get there early in the day to enjoy a mind-boggling 3.5-hour city walk to magnificent squares and the well-loved River Arno, a cultural circuit which -fittingly- starts and ends at Piazza della Signoria.

Day 2:    Walk from Settignano to Fiesole (8 - 16 km / 5 - 10 mi)

Zoom uphill on a 25-minute city bus ride to the village of Settignano, where your walk commences. And not just any walk, this one has you gazing out over lines of cypress trees, grey-green olive groves and Renaissance villas, while the whole city of Florence spreads out at your feet. Stroll through charming Fiesole and tour its intriguing Etruscan ruins, Roman amphitheatre and Franciscan monastery.

Challenge: 3/6 hours, 8 - 16 km / 5 - 10 mi, 345/565m ascent, 225/565m descent

Day 3:    Selection of walks in Greve in Chianti (11.4 -10 km / 7 - 6 mi)

Take your luggage and jump on a local bus or book a private transfer to Greve in Chianti, a rustic market village and the capital of this renowned wine-producing region. Check in at your hotel, just briefly, and head over to Le Cantine di Greve where you can sample over 50 different Chianti wines. Take advantage of the remaining daylight hours and amble through gorgeous scenery on your choice of two routes.

Walk A: Greve in Chianti loop via Uzzano
Hike north from Greve’s pretty main square and meld with the picture-perfect Chianti Classico landscape. Stroll past Villa Calcinaia through seemingly endless vineyards of local ‘aziende agricole’, the famous farms where prestigious Chianti wines are produced.

Walk B: Greve loop via Montefioralle
Explore wonderful woodlands with wild vegetation, elegant villas, verdant vineyards and olive groves. Trundle along past age-old abandoned farms, mysterious ruins and stately manors as you make your artistic way to the panoramic hamlet of Montefioralle.

Challenge: 2.5/3.5 hours, 11.4 -10 km / 7 - 6 mi, 425/360m ascent, 450/355m descent

Day 4:    Panzano loop (11.7 km / 7,5 mi)

Set off on a circuit from Panzano, walking nearby hills and quintessential Chianti scenes in a dreamy landscape where forests alternate with vineyards and ancient Roman farmsteads.

Challenge: 4 hours, 11.7 km / 7,5 mi, 385m ascent, 385m descent

Day 5:    Transfer to Monte San Michele and walk to Radda in Chianti (14 km / 8 mi)

A short transfer takes you up to the highest of the Chianti hills, Monte San Michele. Hiking from Badiaccia, you make your way downhill through a forested valley inhabited by centuries-old chestnut trees. The stunning medieval hamlet of Volpaia awaits, nearly hidden amongst castles and vineyards. Pause at a fine ‘enoteca’ wine shop to tickle your tastebuds with a glass of red then press onward to reach Radda in Chianti.

Challenge: 5/3 hours, 14 - 12 km / 8 - 7,5 mi, 505m ascent, 670m descent

Day 6:    Radda in Chianti round walk (15.8 km / 10 mi)

What a perfect plan! A quiet, relaxing day to bask in the Tuscan sun and go for a scenic walk through Radda’s old town centre. Wind along narrow lanes and wander up to Santa Maria Novella, with its simple facades and ornate interior. Linger among vineyard-covered slopes just outside town and treat yourself to a glass of Chianti Gallo Nero, THE local work of art.

Challenge: 5 hours, 15.8 km / 10 mi, 585m ascent, 585m descent

Day 7:    Travel to Siena

Grab your luggage and jump on a local bus or get in the taxi for a pre-arranged private transfer to marvellous Siena, famous for its ‘Palio’ horse race, held every two years in the most beautiful of shell-shaped squares, la Piazza del Campo. Of course the Duomo, too, is a must-see architectural treasure along with an array of imposing medieval palaces. History comes alive here, as you meander down narrow lanes in this fantastically preserved Italian gem.

Day 8:    Arrivederci Tuscany!

Your self-guided walking holiday comes to an end after breakfast. Extra nights can be booked in Siena to allow time to explore the old city centre, exquisite museums, sumptuous galleries and infinite churches. A city which is perhaps best understood from above, with views from the tip top of the bell tower.


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 Camille (Firenze)
Hotel Camille *** (Firenze)

Located in the historic center of the cradle of the renaissance, Hotel Camilla is your place to reach all the iconic city masterpieces. Just five minutes walk from the famous Santa Maria del Fiore Cathedral, you can enjoy your stay in a completely renewed building offering all the confort you would expect. Near the hotel you can find the famous San Lorenzo market in which you can find excellent typical local foods.


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)
la Bottega di 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. 


Hotel Park Palace**** (Firenze)
Hotel Park Palace**** (Firenze)

A real Florentine style Villa which offers a cozy atmosphere throughout the entire Hotel and its 26 lovely rooms. Only minutes away from the historical centre of Florence where one can visit all of the most famous monuments like the Florence Dome, Palazzo Pitti, and the Uffizi.


Albergo del Chianti (Greve in Chianti)
Albergo del Chianti*** (Greve in Chianti)

Albergo del Chianti, a cozy hotel in the center of Greve, in one of Italy’s most beautiful squares. Besides the nice rooms, you can sit at the bar or choose a nice table in the cosy restaurant, or in the beautiful terrace in the garden with pool view.


Hotel Palazzo San Niccolò ****(Radda di Chianti)
Hotel Palazzo San Niccolò ****(Radda di Chianti)

A sumptuous historic residence in the main square of Radda in Chianti, a village of history and vineyards in the Sienese Chianti. Full of charm, among art nouveau frescoes, terracotta floors and ancient ornaments, the hotel fulfills every desire for beauty and comfort. On the ground floor, the small garden hosts breakfast and wine bar.


Hotel Chiusarelli ***(Siena)
Hotel Chiusarelli ***(Siena)

Hotel Chiusarelli is located in the city centre of Siena and finds its natural setting in a neoclassical villa built around 1870. You will be pleased to stay in a structure that has been completely renovated, keeping it in harmony with the original style of the palace and with its magnificent frescoed rooms.



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:

   www.trenitalia.com (train)

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' accommodation in selected B&Bs, hotels and agriturismo with breakfast
  • The bed & breakfast in Radda in Chianti will not provide breakfast in the accommodation, clients will be given a voucher to have breakfast in a nearby bar
  • 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
  • Digital detailed route notes and maps in English
  • Access to the trip on our navigation app
  • 24-hour telephone assistance

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
  • Shipment of printed documents to the first accommodation

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