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The heart of Chianti
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5 days
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price from GBP 338
The heart of Chianti

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The heart of Chianti

The heart of Chianti - 5 days

The heart of Chianti - 5 days

Discover the genius behind the “Chianti Classico and Gallo Nero” wines by walking through the celebrating vineyards where they are produced. Nestled amidst the flourishing art cities of Florence and Siena, the Chianti region offers natural beauty and incomparable culinary treasures such as the world famous Chianti wines and delectable homemade olive oil. Walk along cypress lined country roads and strade bianche, gravel roads, traversing forests of oak, beech and chestnut. As the Tuscan sun shines above and the golden Chianti countryside reflects your delight, you will feel as if you have stepped into a Renaissance painting.

Day 1: Arrive in Greve in Chianti
Day 2: Tree route options
Day 3: From Monte San Michele to Badiaccia to Volpaia to Radda, 12-14 km
Day 4: Radda in Chianti loop walk, 15,8 km
Day 5: Arrivederci Siena

Day 1:    Arrive in Greve in Chianti

Arrive in 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.

Day 2:    Tree route options

Walk A: Greve in Chianti loop via Uzzano,11,4 km
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, 10 km
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.

Walk C: Panzano loop, 11,7 km
The walk is made up of a loop out of Panzano. You take the local bus to Panzano from where 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.

Day 3:    From Monte San Michele to Badiaccia to Volpaia to Radda, 12-14 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.

Distance: 12-14 km

Elevation gain: +506/-668 m

Day 4:    Radda in Chianti loop walk, 15,8 km

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.  

In the afternoon 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.

Distance: 15,8 km

Elevation gain: +586/-586 m

Day 5:    Arrivederci Siena

Our services end after breakfast, unless you have chosen to add extra nights in Siena


Nights in double room with breakfast

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 comfortable and clean rooms with TV, free Wifi 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 back to the early eighteenth century and is a building originally owned by the noble Bulgarini family. Rooms are simple and clean without air conditioning. Wifi doesn't work very well. Breakfast is normal. Staff courteous and welcoming.

practical info

You can find more information in the "accommodation" section: we always select your accommodation for their character and comfort. You will always be booked in a private, en-suite room, with breakfast included. 

Luggage transfer (max. 20 kg)  from one hotel to the hotel is included in the price. 

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.

To return from Siena to Florence, the SITA-TRA.IN bus station is very close to the hotel and busses leave every 30 minutes. From Florence, you can reach both Pisa and Bologna by train.

Check train and timetables on:

Thanks to our special APP, you will be able to follow the track of the whole trip on your mobile phone, with no need for internet. GPS tracks are available on request.


What is included

  • 4 Nights in double room in *** hotels and B&B  with breakfast
  • transfer Greve in Chianti-Badiaccia and luggage to Radda in Chianti
  • maps and detailed description of the itinerary
  • Medical and luggage travel insurance
  • 24h phone assistance

What is not included 

  • Transfers to the starting location and from the arriving location of the tour
  • lunches and dinners, if not otherwise stated
  • visits and entrance fees - tips
  • personal expense
  • possible sojourn taxes
  • everything that is not mentioned in the "What is included" section.

Optional Services

These services can be added to the ones included in the base price of the tour:

  • Single room supplement
  • cancellation insurance
  • Transfers to reach the starting location or to leave the arriving location of the tour, which will be quoted on request.
Is this trip for me?

Choose this trip of you'd like to immerse yourself in the iconic beauty of Chianti and explore its picture-perfect landscapes. It's a short, sweet and easy trip, suitable for beginners, that can be extended with extra days and guided tours in Florence and Siena. 

S-Cape Countryside Travels srl
Borgo Allegri 16R
50122 Firenze FI
P. IVA 05227330486

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