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Welcome to Hooked on Walking and our walking holidays in Italy. This particualr hiking vacation in Italy is in the region of Tuscany. Indeed Tuscany is a very large region but ths walk will take you through the area of Tuscany which is the most photographed and therefore you should experience the type of scenery found on many calanders and postcards from the region. This walking holiday has been graded as a level 2 self guided walking tour. This really is the Tuscany that you always have dreamt of. You will walk in the rolling hills very often portraited in Renaissance paintings and filmed in todays movies, a landscape with a deep blue sky, golden ochres and lush greens. From the famous vineyards of Vino Nobile and Brunello to walled medieval and renaissance boroughs visiting superb churches and abbeys with comfortable accommodations and typical restaurants and locandas. You will see high cypress trees, holm oak, broom, in the fields wheat, vines, chestnuts and barely. Look closely and you might see, wild boars, foxes, porcupines, badgers, buzzards and much more.
Day 1 Arrival to Arezzo, explore the old town
Arrival to Arezzo which is one of the wealthiest towns in Tuscany with its production of gold jewellery for shops all over Europe. It has a wonderful medieval city centre. In the San Francesco church there is the famous Piero della Francesca’s fresco “The legend of the true cross” which has been recently restored. You can have a short 1.8 miles, 3km walk in the city centre follow the roads and narrow alleys of the town.
Day 2 Transfer to Castiglion Fiorentino environs and walk to Cortona 10 miles 16km
Our local representative will meet you in Arezzo, they will introduce you to your walking tour and then will take you to the start of your walk. Today you will walk on gravel paths and paths towards Cortona with a nice long descent into your destination. Cortona was founded by the Etruscans whose presence can still be seen in the foundations of the city walls and buildings, Cortona sits on a side of a hill facing the Chiana valley. During the middle ages Cortona became one of the most powerful towns of the area.
Day 3 Cortona – Lake Trasimeno 11.3 miles 18km
Today on your walk you will have stunning views of the Chiana valley and lake Trasimeno, the walk will take you to the site where the troops of Rome under Consul Flaminius where defeated by the Carthagineans under Hannibal in the 217 b.C. Lake Trasimeno is the largest lake in the Italian peninsula with a surface area of 128 km², slightly less than Lake Como, a tectonic lake, 3 million years ago, there was a shallow sea in this part of Umbria. Then a depression formed by geologic fractures, allowed the formation of Lake Trasimeno.
Day 4 Transfer and walk to Montepulciano 6.3 miles 10km
Today a relaxing walk in the Montepulciano countryside passing through a Vino Nobile estate with an exploratory town’s walk in the main roads and narrow alleys of the town. Montepulciano is a medieval walled town built on a limestone ridge with renaissance style palazzi and chuches. You will have stunning views of the Chiana valley, the Vino Nobile vineyards of Montepulciano and the imposing cliff where the town lies.
Day 5 Montepulciano – Pienza 8.75 miles 14km
Today a relaxing walk in gravel roads and paths on the way to the Orcia Valley passing through the medieval walled village of Monticchiello. Today you will have views of towns and the classic tuscan countryside of rolling hills dotted with stone houses and decorated by cypress trees. In 1459 Pope Pius II (also a humanist philosopher) decided to rebuild his hometown (Corsignano) employing the Rossellino (architect) to build a model renaissance tow :“Pienza” (from Pius).
Day 6 Pienza – S.Quirico or Bagno Vignoni 8.75 miles 14km
Today you are walking across rolling hills. Along the route you will pass through the village of S.Quirico d’Orcia, not often found by tourists but very very nice and quiet. Before getting to Bagno Vignoni there is the small village of Vignoni Alto with a very pictoresque medieval citadel.
Day 7 S.Quirico / Bagno Vignoni – Montalcino 12 miles 18km
Today this walk is going to be one of the most varied from evergreen woods to fields and vinyards, today there will be also some steeper hills to climb, but not technically difficult. Today your destination of Montalcino is a medieval hilltop town famous for its imposing “Fortezza”, the Brunello red wine and for honey. Try the wine tasting of Brunello wine at the castle and maybe buy a crate to be shipped home!
Day 8 Departure after breakfast.
Buses are available to reach Siena or Buonconvento railway station where trains are available to Pisa and Bologna.
Difficulty: This is a level 2 tour with walks upto around the 5 hour mark maybe 6 hours for slower walkers but the terrain is not hard.
Accommodation: A mixture of very nice 3 star hotels and guest houses, all comfortably located within the historical centres, most of them are family run.
What is Included
Tour Code TUSDREAM
Price per persons based on 2 persons sharing double room standard
Single room standard ( min 2 persons )
How to get there
The best airport to use is Rome Fiumicino and Rome Ciampino, then by train to Arezzo (around 2 hours). You can also fly into Pisa and Florence, then by train to Arezzo (2.5 – 3 hours)
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Cycling Holidays in Italy