Discovering renaissance masterpieces in romantic Florence
Hiking 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
The Chianti Trail
Self-guided hiking in Tuscany’s Chianti region
Discover the magic of this celebrated wine-producing region, nestled in central Tuscany between the beguiling art cities of Florence and Siena. Hiking on 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.
Walking and wine
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.
| 5 DAYS / 4 NIGHTS | From €695 per person sharing*
*Discounts available for triple rooms. Please enquire for prices. |
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| 8 DAYS / 7 NIGHTS | From €980 per person sharing*
*Discounts available for triple rooms. Please enquire for prices. |
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| ACCOMMODATION | In comfortable hotels and guesthouses 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. |
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| AVAILABILITY | You can start on any day of the week, subject to availability, between April and October. | ||||||||||||
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| OPTIONAL EXTRAS |
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| DIFFICULTY | 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: 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 3: 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 4: Free day in Siena or Radda in Chianti circular walk
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.
Or optional extra circular walk from Radda in Chianti*
Distance: 16 km | Ascent: 586 m | Descent: 586 m | 5 hrs approx.
If you prefer some more time to explore the Chianti countryside, you can opt to 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. An afternoon transfer will take you from Radda to Siena.
*Please let us know at the time of booking if you want to do the Radda loop walk and have an afternoon transfer to Siena. Otherwise, the transfer is arranged for 09:30.
Overnight: Siena
Day 5: 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.
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
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. |
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