8 days
Difficulty grade

  Discovering renaissance masterpieces in romantic Florence

  Walking along the vineyard-covered hills of the Chianti region

  Great wineries to visit and wines to taste

  Classic Tuscan landscape of cypress-lined lanes, medieval villages and forests of oak, beech and chestnut

  Strolling across the Piazza del Campo in Siena, one of Europe’s great medieval cities

Discover the magic of this celebrated wine-producing region, nestled between the beguiling art cities of Florence and Siena. Waling cypress-lined paths atop the rolling, vineyard-covered hills, you will feel as if you have stepped into a Renaissance painting. This is the archetypal Tuscan landscape, with its walled towns and tiny hamlets, abbeys, castles and small churches overlooking shaded piazzas. The countryside is surprisingly serene – you will walk in perfect solitude, often with only the occasional wild boar or pheasant for company, past old farm houses and through quiet forests of oak, beach and chestnut.

As well as natural beauty, the Chianti region also offers incomparable culinary treasures such as delectable homemade olive oil and, of course, the world-famous Chianti wines. The wines of the Chianti region developed in the early 1700’s and walking among the vineyards where the famous grape is grown is a feast for the eyes and the senses.

8 DAY TOUR From €799 per person sharing*

*A high season supplement will apply during peak booking periods.
*A single supplement charge will apply for solo walkers.

ACCOMMODATION In very comfortable hotels on a bed & breakfast basis. All hotels are carefully selected for their location, atmosphere and/or unique services. All rooms are en-suite.
The standard hotels of this trip are listed below. If a hotel is fully booked, then we will book a similar one for you and inform you about the alternative booked.

You can also book additional nights at any of the hotels along the way.

AVAILABILITY You can start on any day of the week, subject to availability, between April and October
7 nights in selected hotels
7 Breakfasts
Private transfer (+ luggage) from Florence to Greve on day 3
Private transfer from Greve to Badiaccia + luggage to Radda on day 5
Private transfer (+ luggage) from Radda to Siena on day 7
Detailed route notes and maps with tracks on
Pre-departure information pack
24/7 telephone support
Flights & travel insurance
Lunches & dinners
Travel to Florence and from Siena
City taxes
Anything else not mentioned in the “included” section
Additional nights before, during or after the walk
Single Room Supplement(s)
Transfer from airport to Florence
Transfer from Siena to airport

This trip is graded easy overall, as the walks are relatively short (the longest walk is 16 km). Having said that, the terrain is hilly so the walks can be quite tiring. The walking trails are a mixture of small gravel roads (strade bianchi), footpaths and mule tracks. They are generally not way-marked but we provide you very detailed route notes and maps so you will have no problem with navigation.


Day 1: Arrive in Florence

After settling into your accommodation, we suggest taking a walk around the magnificent café-fringed piazzas and along the Arno River. This walk takes around 3½ hours and is the perfect way to immerse yourself in this beguiling city of stunning architecture and Renaissance art.

Overnight: Florence


Day 2: Walk from Settignano to Fiesole

Option A

Distance: 8 km | Ascent: 347 m | Descent: 224 m | 3 hrs approx.

Option B

Distance: 16 km | Ascent: 567 m | Descent: 566 m | 6 hrs approx.

After breakfast, a 25-minute local bus journey takes you up into the hills to the start of today’s walk in the village of Settignano. You have a choice of a shorter or longer walk, both delightful trails through an idyllic Tuscan landscape of cypress trees, olive groves, Renaissance villas and with panoramic views over the city of Florence below. Stroll through the charming 7th century town of Fiesole and tour its Etruscan ruins, Roman amphitheatre and Franciscan monastery.

Overnight: Florence


Day 3: A choice of walks in Greve in Chianti

A private transfer is arranged this morning to take 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. In the afternoon, take advantage of the daylight to enjoy a walk around this gorgeous Tuscan countryside by choosing between the two routes below.

Walk A: Greve in Chianti loop via Uzzano

Distance: 11.5 km | Ascent: 425 m | Descent: 447 m | 2½ hrs approx.

A circular walk starting from the attractive main square of Greve in Chianti, through the picture-perfect Chianti Classico area and 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

Distance: 10 km | Ascent: 358 m | Descent: 355 m | 3½ hrs approx.

A delightful walk through rural Tuscany, taking in dense forests, rustic villas, vineyards and olive groves before reaching the panoramic hamlet of Montefioralle, one of the region’s most beautiful villages.

Overnight: Greve in Chianti


Day 4: Panzano loop walk

Distance: 12 km | Ascent: 385 m | Descent: 385 m | 4 hrs approx.

A beautiful looped walk beginning in the village of Panzano. Take some time to explore the quaint medieval streets of this historic town before beginning your walk through the surrounding hills. This classic Chianti trail alternates forests with vineyards, with the added opportunity to discover ancient Roman farmsteads as you go.

Overnight: Greve in Chianti


Day 5: Monte San Michele to Radda in Chianti

Distance: 12-14 km | Ascent: 506 m | Descent: 668 m | 3-5 hrs approx.

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), before continuing on to the medieval walled town of Radda in Chianti.

Overnight: Radda in Chianti


Day 6: Radda in Chianti circular walk

Distance: 16 km | Ascent: 586 m | Descent: 586 m | 5 hrs approx.

Begin the day with a scenic walk around the historic and pretty centre of Radda in Chianti. Wander among the narrow alleyways and take in the evocative walled gardens. As you head out of town through the vineyard covered slopes stop to treat yourself to a glass of Chianti Gallo Nero at one of the celebrated local vineyards.

Overnight: Radda in Chianti


Day 7: Travel to Siena

After breakfast a prearranged private transfer takes you to your final destination, the historic city of Siena. One of Europe’s great medieval cities, Siena is famous for its biannual “Palio” horse race, held in the most beautiful shell-shaped square in Europe: The Piazza del Campo. Wander the narrow streets and immerse yourself in the history of this perfectly preserved jewel of Italy.

Overnight: Siena


Day 8: Arrivederci Tuscany!

Our services end after breakfast, unless you have booked any additional services with us. We would be happy to book additional nights for you in Siena or Florence. Just let us know at the time of booking if you would like to extend your stay.

Getting to Florence

  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.
  • 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 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)

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.
The Chianti Trail
Firenze, Chianti Trail
Chianti walking trail
Tuscan castle
walking the chianti
Chianti farm machinery
Tuscany cypress trees
Tuscan countryside
Siena rooftops
Piazza del Campo, Siena

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