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Walk from Siena, the best-preserved great medieval city in Europe, to Florence, the birthplace of the Renaissance. Paths through the picturesque Chianti hills, with vineyards, olive groves and forests, punctuated by castles, fortified stone villages and cypress trees. Traverse the Chianti Classico wine-growing area and sample the range of magnificent wines. Enjoy two supreme art capitals - with over 60% of the greatest works of art in the Western world.
Chianti & Florence:  Itinerary

Day 1
Arrive in Siena


Day 2
Siena to Dievole
Walking: follow tracks across hills with stonewalled olive groves, vineyards and oak forest to Dievole. (11 miles, 6 hrs)
Cycling: minor roads with long views (11, 14 or 28 miles)

Day 3
Dievole to Gaiole-in-Chianti
Walking: cross a valley to the fortified Romanesque church of San Polo in Rosso, from where paths lead to Gaiole-in-Chianti. (9 miles, 4 hrs)
Cycling: valleys and hills with vineyards, olive groves and picturesque villages. (11 or 15 miles)

Day 4
Gaiole-in-Chianti to Panzano
Walking: farm roads (strade bianche) lead to a ridge, from where a track descends to the valley, continuing past stone farmhouses and vineyards to the hill town of Panzano. (11 miles, 5 hrs)
Cycling: through olive groves and vineyards, forest tracks along the ridge of the Monti dei Chianti. (13 miles)

Day 5
Free day in Panzano
Walking: a short optional walk to Greve-in-Chianti. Return by bus. (6 miles, 2 hrs 30)
Cycling: choice of circular routes on quiet undulating lanes. (10 or 20 miles)

Day 6

Panzano to Strada-in-Chianti
Walking: undulating paths across fertile valleys, with two fine castles. End with a climb to Strada-in-Chianti. (16.2 miles, 6 hrs)
Cycling: through vineyards and olive groves or via M. San Michele (2,925ft), through high forested hills. (range of options from 15-38 miles)

Day 7
Strada-in-Chianti to Florence
Walking: tracks and strade bianche lead through farmland before coming to the outskirts of Florence. Minor roads and pathways for the final 2 miles lead to a panorama of the city and descent to the Ponte Vecchio. (14 miles, 6 hrs 30)
Cycling: minor roads and tracks, with busier roads approaching central Florence or via small villages. (15 or 29 miles)

Day 8
Depart Florence
For enthusiastic walkers there are optional longer walks on most days.


You can extend your holiday in Florence, Siena or Pisa.

Chianti & Florence:


Night 1

*** Antica Torre
Small, characteristic hotel at the edge of the medieval city centre. B&B

***** Grand Hotel Continental
Restored frescoed 17C palazzo in centre of medieval city. B&B
Night 2
**** Villa Dievole
Villa in working wine estate, with pool. B&B

Night 3
*** La Fonte del Cieco
Imaginatively restored town house off the main square. B&B
**** Castello di Spaltenna
Restored medieval castle with Romanesque church. B&B
Nights 4 & 5
*** Fattoria Valle
Converted farmhouse furnished with antiques, with outdoor pool. B&B

*** Villa Le Barone
Converted patrician villa with outdoor pool, gardens and tennis court. HB
Night 6
Il Leccio Residenza d'Epoca
Beautiful 17C villa with pool. B&B

Il Leccio Residenza d'Epoca
Beautiful 17C villa with pool. B&B

Superior Rooms are Suites.

Night 7
*** Hotel River
19C palazzina in quiet Santa Croce area, next to River Arno. B&B
**** Orafi
Chosen for its breathtakingly central location! B&B


Chianti & Florence:



Walking: Forested limestone hills rising to 2,925ft, the lower slopes covered with vineyards and olive groves. A wide selection of farm and forest paths and tracks, small gravel roads and some asphalt in and around towns.
Cycling: minor asphalt and gravel country roads, farm and forest tracks.

When to go

Start any day from 01 Apr to 24 Oct



Of interest.
Worth travelling to see if you are in the area.
Of great interest.
Worth travelling to see if you are in the country.
Of outstanding interest.
  Worth travelling to see if you are in Europe.



On Route


*** Siena: The best-preserved great medieval city in Europe. An abundance of outstanding 14C and 15C art and architecture. Also see the Piazza Del Campo, Scene of the Palio horserace.


*** Florence: Birthplace of the Renaissance and with the Uffizzi, Pitti galleries, churches and museums; the world's leading 'Art city'.


** Chianti Classico Vineyards: The route encompasses a range of Chianti Classico Vineyards, many with world wide reputations.


** Castles of Chianti:Wealth from wine production since the early middle ages made land in Chianti highly prized. To protect these rich wine estates, fortified farms and castles were built. Many of these expanded into fortified stone villages that characterise the area today.


* Gaiole-In-Chianti:Agricultural centre overlooked by the Castello di Spaltenna and its 12C Romanesque church.


* Panzano in Chianti:Characteristic hill village with medieval centre. Nearby (close to Hotel Villa Le Barone) is the Romanesque Pieve di S.Leolino, with a fine 13C Madonna with saints


* Montefioralle:A picturesque fortified village , from which the Vespucci (Amerigo etc) family came has a fine Madonna with child and two angels in the church of S.Stefano, interesting pictures in the presbytery and a castle.


* Greve-in-Chianti:A busy centre in the wine industry, with some fine medieval buildings and arcaded central piazza, distinguished by a statue of Giovanni di Verrazzano (discoverer of Long Island).


Flights & Transport

Recommended Destination Airport: Pisa Florence

There are international flights to Pisa and Florence. From Pisa Airport trains run frequently to Siena (change at Empoli), the start of your trip. The airport in Florence is 5 miles from the train station (airport bus) from where trains run direct to Siena. Return: Buses to Florence airport or train direct to Pisa airport. Most places on route are connected by bus, or taxi.


Pisa Airport to First Hotel - approximately 220 Euros.
Florence Airport to First Hotel - approximately 155 Euros.
Last Hotel to Pisa Airport - approximately 150 Euros.
Last Hotel to Florence Airport - approximately 30 Euros.


No. of luggage moves included: 5

No. of nights with half board (dinner included): Standard 0, Superior 2

Cycle hire: £60 / $108

Shortest / Longest days walk: 2 hrs 30 / 6 hrs 30 hrs

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