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Chianti Wine Trails: Florence to Siena 73

Chianti Wine Trails: Florence to Siena


Follow the wine trails of Tuscany on foot through the wine region of Chianti, nestled between the beautiful cities of Florence and Siena. The Chianti region offers natural beauty and culinary treasures, including world-famous Chianti wines. The rolling Chianti hills are carpeted with olive groves, vineyards, and fields from a Renaissance painting. This region has been producing velvety red wines since the 13th century, and there will be many opportunities during your walks to visit local vineyards and enjoy some wine tasting.

First overnight is in Florence and the last one is in Siena, but we strongly recommend that you spend some extra nights in both cities: Florence, famed for Michelangelo’s statue of David, the Uffizi art gallery and the fascinating Ponte Vecchio over the River Arno; and Siena, the jewel among the Renaissance cities of Tuscany with the imposing Piazza del Campo.


  • Florence, the cradle of the Renaissance and Medieval Siena
  • 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

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Day 1: Arrive in Florence

Arrival in Florence on your own. Depending on the time of your arrival, you have the rest of the day for exploring the numerous sites of the capital city of the Renaissance. We strongly recommend that you book an extra night in Florence before the holiday in order to have time to explore this beautiful city.

  • Accommodation: 3-star hotel in Florence (Hotel Camilla or similar)

Day 2: Settignano to Fiesole | 8-16 km

After breakfast, you take a 25-minute local city bus ride to the village of Settignano, where the walk begins. During the walk, you will enjoy magnificent views of cypress trees, olive groves, Renaissance villas and the whole city of Florence at your feet. You will also stroll through the charming town of Fiesole and tour its Etruscan ruins, Roman amphitheatre and a Franciscan monastery.

  • Walking for the day (option 1): approx. 3 hours, 8 km, ­↑­­­­347 m ↓224 m
  • Walking for the day (option 2): approx. 6 hours, 16 km, ­↑­­­­567 m ↓566 m
  • Accommodation: 3-star hotel in Florence (Hotel Camilla or similar)

Day 3: Greve in Chianti Circular Walks | 10-11.4 km

After breakfast, а transfer takes 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 the 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 Chianti wine is produced.

  • Walking for the day: approx. 2.5 hours, 11.4 km, ­↑­­­­425 m ↓447 m

Walk B: Greve in Chianti 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 scenic hamlet of Montefioralle.

  • Walking for the day: approx. 3.5 hours, 10 km, ­↑­­­­358 m ↓355 m

Day 4: Panzano Circular Walk | 11.7 km

Walk through the hills surrounding the village of Panzano, enjoying the classic Chianti landscape of forests and vineyards and discovering ancient Roman farmsteads in the region.

  • Walking for the day: approx. 4 hours, 11.7 km, ­↑­­­­385 m ↓385 m
  • Accommodation: Albergo Casa al Sole

Day 5: Badiaccia a Montemuro to Radda in Chianti | 14 km

After breakfast, a short car transfer takes you to the highest of the Chianti hills, Monte San Michele, from where 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 to Radda in Chianti.

Day 6: Radda in Chianti Circular Walk | 15.8 km

Today you go for a scenic walk around  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 will reach along the way back to Radda.

Day 7: Siena

After breakfast, a transfer takes you to the marvellous city of Siena, famous for its biannual Palio horse race, held in the city’s famous square: the Piazza del Campo. You have the whole day exploring the architectural treasures of the city, and if it is not enough, you can book an extra night.

Day 8: Departure

Departure on your own or extension upon request.

What to Expect


Accommodation is in selected B&Bs, and 2&3-star hotels, all with en-suite facilities and a good Italian breakfast included each morning. All places have been carefully hand-picked by us, and their quality is regularly monitored. We have tried to choose accommodations that offer friendly service, clean and comfortable rooms and local flavour. Hotel upgrade is possible on request.

Click to view default hotels

Hotels are subject to availability. In case a particular hotel is fully booked for your desired dates, we will replace it with a hotel of equal value and quality level. We will provide exact accommodation details to you upon booking confirmation.


The trip is on a bed and breakfast basis throughout the trip; there are plenty of opportunities for you to taste both the outstanding local cuisine and a wide range of fine regional wines. Dinner is available either from the restaurant in your accommodation or in the town where you stay overnight.

Difficulty & terrain

This is a self guided walk with average daily walking stages taking between 3-5 hours, and you are usually able to choose the route for the day according to your abilities. A basic fitness level is required for enjoying the walks to the maximum (read more about difficulty grades). 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. We strongly advise you to follow only marked trails and never try to shorten the path through the unknown and unmarked terrain. We will provide you with detailed road notes and maps, and you can call our 24/7 local assistance phone number anytime. More detailed info on route navigation will be included in your holiday information pack.

When to go

You can start your holiday every day between the beginning of April and the end of October. Spring and autumn months are a preferred travel period if you want to avoid the summer heat of July and August (If you’d like to catch the famous Palio di Siena, you will have to travel in July or August, however). In September – October, you will enjoy pleasant temperatures and might also be able to catch the regional wine harvest.

Getting there

FCO up-to-date travel advice

Click to view travel options

By plane

Our recommended arrival airports for this holiday are FlorencePisa and Bologna. Other Italian airports are also well connected to the area.

By train or bus

All three airports are connected to the major cities in the area by local transport, which is affordable and offers frequent service. From Florence airport, you can take a 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. Train schedules can be checked on the Trenitalia website, or you can use the Omio planner above.



  • 7 nights in selected B&Bs and 2 and 3-star hotels
  • 7 breakfasts
  • Luggage transfers on all walking days
  • Transfer from Florence to Greve in Chianti on Day 3
  • Transfer from Greve in Chianti to Badiaccia on Day 5
  • Transfer from Radda in Chianti to Siena on Day 7
  • Holiday information pack including GPS-checked and regularly updated route notes and maps (digital copy sent by email and a hard copy delivered at the first hotel)
  • 24/7 telephone support by our local office/representative


  • Airfare and connecting land transfers
  • Lunches and dinners, drinks and snacks
  • Travel insurance (required – get a quote online)
  • Personal expenses
  • Any items not specifically mentioned as ‘Included’ in the programme

Options, extras & supplements

  • Supplement applies to members of a group who require a single room / single use of a double room
  • This holiday is available for solo travellers; a supplement will be charged as accommodation and luggage transfer costs are not shared (we never mix and match – solo travellers will be accommodated in single rooms)
  • Extra nights
  • Hotels upgrade is possible on request
  • The tour can be arranged as a 5-day/4-night programme