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Terra di Siena Hike Dream - Walking - Itinerary

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Montepulciano
Sant'Antimo
Siena

Day 1: BIENVENUTI! Arrive in Montepulciano and explore the old town

The Zephyr guide will meet you in Montepulciano, introduce you to your walking tour, answer your questions, and provide you with route maps and notes.

Walk Details: EASY- 2 km exploratory walk in the side roads and narrow alleys of town.

About The Town: Montepulciano is a medieval walled town built on a limestone ridge, with many beautiful Renaissance style palazzi and churches. The town is very pedestrian-friendly and a great place to walk.

Special Event of the Day: Taste the famous Vino Nobile wine from a streetside cafe in the middle of town.

Day 2: Montepulciano - Monticchiello - Pienza

The Day's Highlight: Views of lovely small towns amid the classic Tuscan countryside of rolling hills, dotted by stone houses and cypress trees. A relaxing walk along gravel roads and paths in the Orcia Valley, passing through the medieval walled village of Monticchiello.

Walk Details: EASY- 13 km on gravel roads and paths with one big uphill to Pienza.

About The Town: In 1459 Pope Pius II, also a humanist philosopher, decided to replicate his hometown of Corsignano, employing the renowned architect Bernardo Rossellino to build a model Renaissance town. The result is Pienza, named after Pius.

Special Event of the Day: Walk along the top of the city walls, looking out over the Tuscan countryside at sunset, before retiring to a cafe to taste the great pecorino (sheep's) cheese.

Day 3: Pienza - San Quirico D'Orcia - Bagno Vignoni

The Day's Highlight: Descend from Pienza into the scenic Orcia river valley, walking through postcard landscapes of rolling hills and deep green (or golden, depending on the season) wheat fields. Along the route you will pass through the village of San Quirico d'Orcia, less frequented by tourists, on your way to Bagno Vignoni, the beautiful "resort" town with its restful natural baths.

Walk Details: EASY - 14 km through rolling hills but mainly downhill from Pienza.

About The Town: Bagno Vignoni is a tiny village with Renaissance thermal baths.

Special Event of the Day: Go for a swim in the hot springs of Bagno Vignoni.

Day 4: Bagno Vignoni - St. Antimo

The Day's Highlight: Classic views of Tuscan towns and countryside.

Walk Details: MODERATE - 13 km on dirt paths through various terrains including evergreen woods, fields, and vineyards. Some steeper hills, but not technically difficult.

About The Town: The Abbey of St. Antimo is a beautiful church abbey founded by Charlemagne in 781, which has inspired many poets and painters and where Benedictine monks chant daily. Close to the Abbey is the small village of Castelnuovo.

Special Event of the Day: Visit the St. Antimo Abbey when the monks are gathered for chanting.

Day 5: St. Antimo - Montalcino

The Day's Highlight: A walk through forest and along ridges, looking out over the Tuscan slopes.

Walk Details: EASY-MODERATE - 12 km of mixed paths with an uphill heading to the hilltop town of Montalcino.

About The Area: Montalcino is a medieval hilltop town famous for its imposing "Fortezza" (fortress), the delicious Brunello red wine, and honey.

Special Event of the Day: Buy a bottle of Brunello in Montalcino and sip it in the Fortezza, with sunset views of the surrounding area.

Day 6: Montalcino - Buonconvento

The Day's Highlight: A walk past vineyards that supply Montalcino's famous wine makers.

Walk Details: EASY or MODERATE - 15 km (or 20km depending on stopping point), mostly descending from Montalcino.

About The Town: You will stay at the lovely agriturismo of Pieve a Salti, and sample delicious farm-grown products, or continue on to the nearby town of Buonconvento, a charming spot off the normal tourist route and a great place to see real small-town life in Italy.

Special Event of the Day: Get up early to take a walk through Montalcino's streets, with views of the surrounding peaks and hills.

Day 7: Buonconvento - Abbazia di Monte Oliveto and a transfer to Siena

The Day's Highlight: The view from Chiusure and the outstanding frescoes of the main cloister of Monte Oliveto Abbey. The abbey was founded in 1313 by a Sienese nobleman. It is a Benedectine order monastery with world-renowned frescoes and carvings by Sodoma, Signorelli, and Fra Giovanni da Verona.

Walk Details: EASY - 11 km on double tracks and gravel roads, mostly ascending to Monte Oliveto, with views of the Crete Senesi (Siena Clays) along the route.

About The Town: Siena is the best preserved medieval city in Europe, a true masterpiece of art and architecture with its Gothic Duomo, museums, and famous buildings.

Special Event of the Day: Purchase your lunch in the morning in Buonconvento and eat it en route.

Day 8: Ciao Ciao!

The Day's Highlight: A final walk through Siena, visiting the alleys and central piazza.

Walk Details: EASY - stroll through the streets of Siena at your own pace.

Special Event of the Day: Visit the shell shaped square "Il Campo", the scene of the mad horserace "The Palio".

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