+44 (0)1506 635399 info@hookedoncycling.co.uk
+44 (0)1506 635399 info@hookedoncycling.co.uk

Tuscany Chianti Walking

Booking Form
Enquiry Form
Full Name*
Email Address*
Your Enquiry*
* I agree with Terms of Service and Privacy Statement.
Please agree to all the terms and conditions before proceeding to the next step

Please click the link below to book this tour

Proceed Booking

Proceed Booking

Save To Wish List

Adding item to wishlist requires an account

Homepage > Italy > Tuscany Chianti Walking
  • Duration: 4 or 7 Nights
  • Difficulty: Level 1-2
  • Tour Type: Self Guided
  • Availability: Daily from 1st April to 31st October
  • Location: Florence
Tour Details

Want to combine your love of the outdoors and have a weak spot for some fantastic red wine; we have the answer in our Tuscany walking holidays. This particular trip takes in the beautiful Italian cities of Florence and Siena in the region of Tuscany, Italy. Needless to say, this walking holiday in Italy takes you through some great scenery, the major wine region of Chianti and also through some of Tuscany’s very historic towns and cities. This hiking vacation in Italy is available as a four and seven-night self-guided walking tour.

Your hiking vacation in Tuscany really is what you imagined Tuscany to be. Between the artistic masterpieces of Florence and Siena, we find the “Chianti Classico” hills, covered with vineyards producing world-famous wines, as well as excellent olive oil. Walking along the Chianti’s footpaths, cypress-lined roads and strade Bianche that cross-forest of oak, beech and chestnut you will feel as if you have just walked into a renaissance painting, dotted with well-preserved towns and villages, imposing Renaissance villas and picturesque stone farmhouses where the locals maintain age-long traditions.

Starting Location


Price Includes

  • 4 or 7 nights bed and breakfast
  • Information Pack
  • Transfers as per schedule
  • Luggage transfers
  • Accommodation as mentioned
  • GPS Files on request
  • Navigation by Smart Phone App

Price Excludes

  • Transport before and after tour
  • Single Rooms
  • Flights
  • Public Transport
  • Entrance to Attractions
  • Accommodation Upgrade
  • Travel Insurance
  • City Tax
Trip Info


Walking distance varies from 5-10 miles 8 to 16km. The hilly countryside can be demanding and it requires some stamina and a moderate to good physical condition. The walks are along uneven footpaths, mule tracks and strade bianche (small gravel roads).

Accommodation: Subject to Change

Choose between our standard, selected 3 star B&B’s in Florence and Greve, simple but nice B&B in Radda and cosy 2-star hotel in Siena or upgrade to 4-star hotels in Florence and Radda, a 3-star hotel in Greve and Siena.  Accommodation is based on double room occupancy with private en-suite facilities. Throughout the trip, there are plenty of opportunities to taste not only the excellent local food but also the many famous wines of the region.

Standard Grade

Florence:        Hotel Camilla

Greve:             Albergo Casa al Sole

Radda:           Affittacamere Giovannino (provides breakfast voucher)

Siena:             Hotel Cannon d’Oro


Florence:        Hotel Park Palace

Greve:             Albergo del Chianti

Radda:           Hotel Palazzo San Niccolo

Siena:             Hotel Chiusarelli

Best Travel Season

The best season for planning this tour is in spring and autumn. Not only the weather but also nature is at its best during these months. July and August can be very hot making the walks seem more strenuous. April and November can be rainy and muddy and sometimes unexpectedly cold.


Throughout the hill country in Italy, you can expect temperatures between 10 – 25 °C in spring and autumn that can reach 35°C in July and August. Mornings can be chilly and misty but it warms up as the day goes by. Showers are common in spring and autumn, although not every day and they tend to be either short and intense or prolonged but light.

Travel Insurance

It is a requirement of booking this tour with Hooked on Walking that you have suitable travel insurance which covers you for the chosen activity and for emergency evacuation and hospital care.


4-night break includes days 1,3,5,7,8

Day 1Arrival in Florence.

Arrival in Florence. If you arrive in the morning, you can make a city walk. The city walk passes by the most beautiful streets and squares and the most important sights. The walk starts and ends at the Piazza della Signoria, it is 5 miles, 8 kilometres long and takes about 3.5 hours

Day 2Settignano to Fiesole

A 25-minute city bus ride takes you to Settignanoe where the walk starts. The walk leads you through the characteristic Tuscan countryside to the remarkable town of Fiesole, walking through cypress forests and olive groves that offer magnificent views of the city and the Duomo. In Fiesole, this beautiful Etruscan-come-Roman town there are many things to visit, the Roman Theatre and Baths, a Romanic church, the Franciscan monastery, as well as the remains of the Etruscan civilisation. Return to Florence with the local city bus.
5/10 miles 8/16 km,  up 347/567m,  down 224/566m,  3/6 hours

Day 3Hills and vineyards north of Greve in Chianti

After breakfast, you will have a private transfer to Greve in Chianti where you can check into your hotel where you will spend 2 nights. Visit Greve, capital of the Chianti wine-producing region, discovering this unique and charming market village. Then walk along a ridge overlooking a quintessential Tuscan view of Renaissance villas, charming farmhouses and cascading vineyards to the fortified ancient village of Montefioralle, the birthplace of Amerigo Vespucci, who gave America its name.
6.2 miles 10 km, up 358 m, down 355 m,   3.5 hours

Day 4Greve Circular walk

First transfer to Panzano, a small village a few kilometres south of Greve by bus and then a lovely loop walk which takes you 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. Transfer back by bus.
7.3 miles 11.7 km up 385 m, down 385 m,  4 hours.

Day 5San Michele to Radda in Chianti

First a transfer to San Michelle and the highest hills of the Chianti region. Walking to Radda in Chianti you descend through a forested valley full of century-old chestnut trees until you reach the vineyards surrounding the hamlet of Volpaia, one of the most beautiful and nicest situated villages of the Chianti. A fine ‘enoteca’ will make you pause here. The last part of today is through the typical Chianti landscape woods and vineyards, passing by the church of Santa Maria Novella, on the other side of the valley you can already see Radda.
8.7 miles 14 km, up  506 m, down 668 m,   5 hours.

Day 6 Radda in Chianti round walk

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.
9.8 miles 15.7 km, up  586 m, down 586 m,   5 hours.

Day 7 Siena

After breakfast, you will have a private transfer to Siena where you can spend the day discovering this town famous for its “Palio” horse race held twice yearly in one of the most beautiful squares of Europe (judges say). Don’t’ miss and the black and white marbled Duomo and meandering through the narrow streets and alleys. In short, this is one of the most perfectly preserved middle age cities in Italy.

Day 8Departure

Tour complete after breakfast. The day is at your leisure to explore this beautiful city more with its innumerable masterpieces


How to get there

Pisa and Florence’s airports have regular international flights. Several low-cost carriers serve Pisa and Bologna.
There is a regular bus and train service from Siena to Florence
Taxi from Florence airport to downtown around 20€
Train from Pisa airport to Florence 5€
Siena to Florence by bus 6€

Trip extension

You can extend your trip by booking extra nights in all the accommodations on the route. We advise Florence, Siena and Radda. You can also combine your trip with a stay in other towns and cities in Tuscany and Umbria.

Book Now

2024 Prices – For a complete tour price breakdown please click the book now button and select your holiday tour date. Prices will then be listed.

 Tour Code Prices From (per person) Book Now
Tusc1-S (4 Nights)   from £549 Book Now
Tusc1-S (7 Nights)   from £802 Book Now
Tusc1-Upgrade(4 Nights) from £622 Book Now
Tusc1-Upgrade (7 Nights)  from £997 Book Now
Tour Images