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Welcome to Hooked on Walking holidays and our walking holiday in the Chianti region of Tuscany. Needless to say this walking holiday takes you through some great scenery, a major wine region of Chianti and also through some of Tuscany’s very historic towns and cities in particular Florence and Siena. This walking holiday is available as a four or seven night self led walking tour.
Between the artistic masterpieces of Florence and Siena we find the “Chianti Classico” hills, covered with vineyards producing world famous wines, as well as excellent olive oil. Walking along the Chianti’s footpaths, cypress lined roads and strade bianche that cross forest of oak, beech and chestnut you will feel as if you have just walked in to a renaissance painting, dotted with well preserved towns and villages, imposing Renaissance villas and picturesque stone farmhouses where the locals maintain age-long traditions.
Available from 1st April to 31st October
4 or 7 night tour
Level 1-2 self guided tour
Day 1 Arrival in Florence.
Arrival in Florence. If you arrive in the morning, you can make a city walk. The city walk passes by the most beautiful streets and squares and the most important sights. The walk starts and ends at the Piazza della Signoria, it is 8 kilometres long and takes about 3,5 hours 
Day 2 Settignano to Fiesole
A 25 minute city bus ride takes you to Settignanoe where the walk starts. The walk leads you through the characteristic Tuscan countryside to the remarkable town of Fiesole, walking through cypress forests and olive groves that offer magnificent views of the city and the Duomo. In Fiesole, this beautiful Etruscan-come-Roman town there are many things to visit, the Roman Theatre and Baths, a Romanic church, the Franciscan monastery, as well as the remains of the Etruscan civilisation. Return to Florence with the local city bus. 9 km, up 300m, down 100m, 4 hours
Day 3 Greve in Chianti
After breakfast you will have a private transfer to Greve in Chianti where you can check into your hotel where you will spend the night. Visit Greve, capital of the Chianti wine producing region, discovering this unique and charming market village. Then walk along a ridge overlooking a quintessential Tuscan view of Renaissance villas, charming farmhouses and cascading vineyards to the fortified ancient village of Montefioralle, the birthplace of Amerigo Vespucci, who gave America its name 9 km, up 250 m, down 250 m, 4 hours
D ay 4 Greve circular walk
Today’s walk takes you to Panzano, a small village a few kilometres south of Greve. Walk along a ridge over looking the Val di Greve and Val di Pesa valleys you will have a great Tuscan view of the Renaissance villas, charming farmhouses and cascading vineyards. 9 km up 350 m, down 450 m, 4 hours.
Day 5 San Michele to Radda in Chianti
First a transfer to San Michelle the you walk to Radda in Chianti, you descend through a forested valley full of century old chestnut trees until you reach the vineyards surrounding the hamlet of Volpaia, one of the most beautiful and nicest situated villages of the Chianti. A fine ‘enoteca’ will make you pause here. The last part of today is through the typical Chianti landscape woods and vineyards, passing by the church of Santa Maria Novella, on the other side of the valley you can already see Radda. 13.6 km, up 450 m, down 450 m, 5.5 hours.
Day 6 Circular walk
Today is an easy, relaxing day. A short circular walk in the neighbourhood of Radda in Chianti leaves you plenty of time to explore the town that has remained practically unchanged since the middle ages. You can also stop at the wine cellars and try some Chianti wine! 8.6 km, up 250 m, down 350 m, 4 hours. 
Day 7 Siena
After breakfast you will have a private transfer to Siena and spend the day discovering this town famous for its “Palio” horse race held twice yearly in one of the most beautiful squares of Europe (judges say). Don’t’ miss and the black and white marbled Duomo and meandering through the narrow streets and alleys. In short this is, one of the most perfectly preserved middle age cities in Italy.
Day 8
Tour complete after breakfast. The day is at your leisure to explore this beautiful city more with its innumerable masterpieces
Best travel season
The best season for planning this tour is in spring and autumn. Not only the weather but also nature is at its best during these months. July and August, can be very hot making the walks seem more strenuous. April and November can be rainy and muddy and sometimes unexpectedly cold.
Level of walking
Walking distance varies from 10 to 16km. The hilly countryside can be demanding and it requires some stamina and a moderate to good physical condition. The walks are along uneven footpaths, mule tracks and strade bianche, (small gravel roads).
Climate
Throughout the hill country in Italy you can expect temperatures between 10 - 25 °C in spring and autumn that can reach 35°C in July and August. Mornings can be chilly and misty but it warms up as the day goes by. Showers are common in spring and autumn, although not every day and they tend to be either short and intense or prolonged but light.
Accommodation
Choose between our standard, selected 3 star B&B’s in Florence and Greve, simple but nice B&B in Radda and cosy 2 star hotel in Siena or upgrade to 4 star hotels in Florence and Radda, 3 star hotel in Greve and Siena. Accommodation is based on double room occupancy with private en-suite facilities. Throughout the trip there are plenty of opportunities to taste not only the excellent local food but also the many famous wines of the region.
4 night break includes days 1,3,5,7,8
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What is Included
- 4 or 7 nights Bed & breakfasts
- Accommodation as above.
- Information Pack
- Luggage transfer
- Maps and walk instructions
- Transfers as per schedule
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Extras
- Transport before and after tour
- Single Rooms
- Flights
- Accommodation upgrade
- Entrance to attractions
- public transport
- Flights
- Travel Insurance
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2010 Prices
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Tour Code Tusc1-S Standard
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Tour Code Tusc1-U Upgrade
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Price per persons based on 2 persons sharing double room 4 / 7 nights
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£462 / £660
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£563 / £795
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Single person 4 / 7 nights
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£765 / £1095
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£903 / £1230
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Extra Nights B&B per person in Florence
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£52 Double, £70 Single
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£83 Double, £147 Single
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Extra Nights B&B per person in Siena
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£53 Double, £99 Single
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£70 Double, £93 Single
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How to get there
Florence airport has regular international flights. Several low cost carriers serve Pisa and Bologna.
There is a regular bus and train service from Sienna to Florence
Taxi from Florence airport to downtown around 20€
Train from Pisa airport to Florence 5€
Siena to Florence by bus 6€
Flying to or from Pisa Airport? Book your express, low-cost airport transfer with Terravision. From Pisa G. Galilei Airport direct to Florence City Centre CLICK HERE
Trip extension
You can extend your trip by booking extra nights in all the accommodations on the route. We advise Florence , Siena and Radda. You can also combine your trip with a stay in other towns and cities in Tuscany and Umbria.
To view other walking holidays in Italy Sicily, Piemonte, Umbria, Cinque Terre, Dolomites, Sardinia, Amalfi Coast, Elba, Sicily Active Volcanoes, Tuscany Dream, North of Siena, Lake Como, Glimpse of Sardinia, Pisa to Lucca, Edge of Tuscany.
Find with Tuscany Accommodation your perfect place in Tuscany
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