Walking tour of Tuscany
Chianti and Val d’Orcia

From Greve to Montepulciano
9 days / 8 nights
85 Km Walking in Tuscany

  • Duration

    9 days / 8 nights

  • Location

    From Greve to Montepulciano

  • Length

    85 Km of classic Tuscany

  • Price

    From 1050 € / Person

Walking tour of Chianti and Val d’Orcia

Nice fusion of both of our walking tours. You not only get to visit the beautiful Chianti area but also spend time exploring the wonderful landscapes of Val D’Orcia.

Timeline

  • The tour start in Greve in Chianti

Departure from Greve in Chianti

Greve in Chianti, the entrance gate to the Chianti region. Have a relaxing walk in and around the main square and feel the peaceful ambient of this area of Tuscany.

Restaurants, wine rooms and cellars offer a variety of local dishes where you can also taste wine, olive oil, and Vin Santo.
Greve offers a number of open markets, fairs and events where Chianti wine is the main character, depending on your tour dates, you will be able to see the importance of the wine for this region.
Afterwards, relax in your charming room, have a nice hot shower and a good night’s rest before your tour starts…

Day 2 – Greve to Panzano

From Greve, you will have a nice walk to Panzano between vineyards and beautiful landscape. Stop at Montefioralle, one of the most ancient villages of Chianti, still today enclosed within the original walls. Its cool passageways and overarching houses provide one of the best surviving examples of mediaeval rural village architecture in Tuscany.

There is a nice trattoria for lunch. After Montefioralle, you will reach la Pieve di Cresci, the oldest in the Chianti region whose origins date back to the year 963.

You’ll be here half your way to Panzano. Leaving la Pieve di Cresci, the walk follows towards Badia a Passignano an ancient monastery dating back to 395, then continue your descent hike straight to Panzano, an attractive town located on a high ridge on the scenic Via Chiantigiana, exactly halfway between Florence to Siena. The Castle and churches are worth visiting.
Have a rest and a good dinner in one of the several fine restaurants of the town.

Greve to Panzano

Distance

16 Km /9.9 Mi

Details
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Day 3 – Panzano to Radda in Chianti

In today’s hike, you will be walking through some of the most important and renowed vineyards of the Chianti area. The smell of grapes and wine will be your companion throughout the day.

Stop at Volpaia, a fully restored medieval village with an impressive amount of culture and history, that is also home to some of the most impressive wine cellars in the region.

Afterwards, you will continue towards Radda, situated on a hill covered with woods and extensive vineyards forming the watershed between the Pesa and Arbia valleys. Palazzo della Podestà and Chiesa di San Niccolò are some of the buildings that are worth visiting in Radda.

Distance

15.8 Km / 9.7 Mi

Details
Asphalt
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Day 4 – Radda to Castellina

In this hike, The views from many points will be spectacular, a journey for real nature lovers. You will end up in Castellina, a tiny hilltop town. Here you can admire the Rocca Comunale, a 15C Fortress, and the Church of San Salvatore.

Along Via Ferruccio, you will find Palazzo Ugolini and Palazzo Biancardi as well as a number of shops with local products and some good restaurants where to have a rest and a good lunch.
We’ll pick you up at 2.00 pm and drive down to Siena on the winding, panoramic road Chiantigiana driving through hills planted with olive groves, cypresses and vines.
Spend afternoon in Siena at your own pace, Italy’s loveliest medieval city, Siena offers lots of fantastic sights and attractions. Palazzo comunale, Torre del Mangia, Il Duomo and Baptisterio just to mention a few.

Distance

14.5 Km / 9.1 Mi

Details
Asphalt
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Day 5 – Siena whole day, transfer to Montalcino

Morning in Siena, still time to visit the places you missed the day before and some shopping in the many one-of-a-kind boutiques and shops you can find at every corner of the city.
We’ll pick you up at 5.00 pm and drive down to Montalcino through the local, panoramic road of Ville di Corsano. The majestic Val D’Orcia, world heritage site of UNESCO, an area that has become famous for the absolute beauty of its landscapes and its perfectly preserved medieval villages, churches and Abbeys. Stories from the past brought to life, you will feel the history under your feet and all around you.
Montalcino, the town of the brunello wine, will be your home tonight.
Wine is present in every corner and aspect of this fantastic place, from cellars to room wines, restaurants and shops, you will smell the floral, fruity, spicy and wood odors of the Brunello wine everywhere.
Take a nice walk along its narrow streets, purchase a bottle of Brunello or two and enjoy a gourmet dinner with local delicious fresh products.

Day 6 – Montalcino to San Quirico d’ Orcia

Visit the historical center of Montalcino and explore the local crafts and products, you can also stop at the old town wine shop for a tasting of the superb wines of the areA. The hike from Montalcino to San Quirico will be between vineyards and grain fields.

The perfect trail for quiet contemplation that will provide a wonderful frame of outstanding natural beauty. In San Quirico, and after a rest, visit this small, absolutely charming town with its beautiful buildings and fortified walls, shops, restaurants and cafés. There is a lot to see, the Collegiata Church, Palazzo Chigi, Church of San Francesco, Santa Maria Assunta and Horti Leonini just to mention a few..

Distance

11.5 Km / 7.5 Mi

Details
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Day 7 – San Quirico to Pienza

On route Vignoni Alto and Bagno Vignoni. The hike from San Quirico to Pienza will be absolutely stunning, you will first get to Vignoni Alto, a small fortified borgo dating back to XI Century, from here you will admire a breathtaking panorama of the whole Val D’orcia.

Following the route to Pienza, you will make another stop at Bagno Vignoni, esteemed thermal locality, a place of extreme beauty with a characteristic small chapel dedicated to St. Catherine built in the center of the porch overlooking a termal pool.

In Pienza, one of the most famous and beautiful hill top towns of the entire Tuscany, Visit the square and historical buildings, Palazzo del Comune, Palazzo Vescovile, Palazzo Piccolomini and the Duomo, after this hike, it will be necessary a super dinner at a nice, local Osteria.

Distance

13.5 Km / 8.6 Mi

Details
Asphalt
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Day 8 – Pienza to Montepulciano

This hike will get you passing through typical Tuscan farmhouses, beautiful open landscapes towards Mount Amiata.

Stop at Monticchiello, a small borgo perched on top of a hill and known as the balcony of the Valdorcia, it retains a truly gothic fascination. After Monticchiello, straight to Montepulciano, a town built along a narrow ridge of limestone, surrounded by an imposing city wall, famous for its renaissance architecture.

You will visit the Piazza Grande, Duomo, Palazzo Pubblico and others. Have also time to taste the “Nobile di Montepulciano”, the town’s winemaking symbol.

Distance

12.8 Km / 7.2 Mi

Details
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Day 9 – Departure

Before you leave Montepulciano make sure you put the cherry on the top of your Walking Tour of Tuscany.
After this tour you will enjoy recovering your energy. With a glass of a good red “Nobile di Montepulciano” in your hand, take the pleasure of a hydromassage in the thermal waters, whose therapeutic and healing properties have been enjoyed since Roman times.

Then let the memories of this Tour come back to your mind… A unique, unforgettable experience!

We hope you enjoyed your Tour !

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