Tuscany Chianti Walking Holiday

Tuscany Chianti Walking Holiday

On our Tuscany Chianti Walking Holiday 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.

Tuscany Chianti Walking Holiday Highlights

  • 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!

Tuscany Chianti Walking Holiday Overview

Detail Description
Destination Tuscany Italy
Holiday Type Self guided walking
Start/Finish Florence/Sienna
Duration 8 days
Grade 2/5
Distance Avg 12km per day
Season April to October.

What we do

We put together the trip for you: reserve the hotels, transfer the luggage and organise your transfers to the start of your itineraries. Each tour includes a complete Road book with detailed itineraries, information for visits along the way, a detailed map and total peace of mind with our 24-hour local support.

We work with local operators through-out each destination that are passionate about their regions.

We can tailor make this tour, if you want to add an extra rest day, spend a few days relaxing before or after the trip just let us know and we will be happy to provide a quotation.

Tuscany Chianti Walking Holiday Itinerary

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.

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.

Tuscany Chianti Walking Holiday Dates & Prices

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

Price per person from €657.

Dates Room Price per person
01/04/2019-12/04/2019 Double / Twin €841
01/04/2019-12/04/2019 Solo €1356
01/04/2019-12/04/2019 Single €1164
01/04/2019-12/04/2019 Triple €729
13/04/2019-28/04/2019 Double / Twin €857
13/04/2019-28/04/2019 Solo €1356
13/04/2019-28/04/2019 Single €1164
13/04/2019-28/04/2019 Triple €744
29/04/2019-30/09/2019 Double / Twin €872
29/04/2019-30/09/2019 Solo €1418
29/04/2019-30/09/2019 Single €1226
29/04/2019-30/09/2019 Triple €760
01/10/2019-15/10/2019 Double / Twin €841
01/10/2019-15/10/2019 Solo €1356
01/10/2019-15/10/2019 Single €1164
01/10/2019-15/10/2019 Triple €729
16/10/2019-31/10/2019 Double / Twin €793
16/10/2019-31/10/2019 Solo €1251
16/10/2019-31/10/2019 Single €1059
16/10/2019-31/10/2019 Triple €657

Included in Tuscany Chianti Walking Holiday

  • 7 Nights in selected B&Bs, hotels and agriturismo
  • 7 BreakfastsPrivate 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


  • 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

Your Accommodation on Tuscany Chianti Walking Holiday

All accomodations are carefully selected because of their location, atmosphere and/or unique services. All rooms are en-suite.
We choose comfortable hotels, farmhouses and B&Bs where all rooms have private en-suite bathroom.
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.

Where you rest your head after an active day is hugely important to us. We go to great lengths to find properties that are unique expressions of the region you are travelling through. Think of them as the charming and intimate garnish atop your trip. 

Whether nestled in the heart of a village or lost in the countryside and surrounded by nature, all accommodations are chosen using a strict criteria of comforthospitality, and authentic charm. We like to use locally run independent small hotels, guest houses and B&Bs instead of the larger “chain” hotels.  All of them are hand-picked, visited, and re-visited by our local partners. On most of our holidays you will be staying in different hotels and their  uniqueness and individual character only adds to the enjoyment of your holiday. You will also benifit with knowledge that your trip is contributing to local economies, and supporting local family run businesses.

You will be welcomed in a double or twin room (2 beds) – based on double occupancy.
All of our rooms have private bathrooms.
Individual rooms are possible upon request when you book; they are subject to availability and incur a supplemental fee.
For biking trips, all of our inns have a safe place to keep bicycles for the night

Getting to Tuscany Chianti Walking Holiday

Flights are not included in the price. Adventure Holidays do not book flights. We will  advise you on best times, dates and airfares to book.
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 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)
www.busfox.com/timetable/ (bus)

From Price pp


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