Walking tour of Tuscany, Chianti area and Val d' Orcia, 10 days 9 nights

Day 1: Arrival Greve. Sleep Greve

Your first night in your departure point...have a nice evening stroll in the surrounding neighborhood and feel the animated, yet peaceful ambient of the Tuscan cities. Restaurants and trattoria are quietly fulfilled with locals and tourists, a charming, multicultural blend of people looking for the same, a taste of the superb local cuisine and the peace and magic of a place full of history... 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 ( stop montefioralle ). Sleep 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, a 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 finerestaurants of the town.

Day 3. Panzano to Radda ( stop Volpaia ). Sleep Radda

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 medival 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.

Day 4. Radda to Castellina. Sleep 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 your last nice dinner of your walking tour of Chianti.

Day 5 - Castellina to Siena. Sleep Siena

After breakfast, we'll come and pick you up to drive you to Siena. It will be a walking journey of the old city centre to admire the splendid palaces and the marvelous Cathedral which you can visit inside, including the Libreria Piccolomini and the adjacent Museo dell'Opera Metropolitana and behind the Duomo, the Baptistery and the Cripta di San Giovanni. Continue to Piazza del Campo, one of the most beautiful in the world with the majestic Palazzo Comunale, go up the Mangia Towner and admire the wonderful views of the town. Other important points not to miss are Hospital of Santa Maria della Scala and its Sala del Pellegrinaio, covered with 15th-century frescoes of daily life. Chiesa di Santa Caterina and Basilica di San Domenico. Your hotel will be in the city centre to allow you to have a nice dinner and enjoy Siena by night.

Day 6 - Siena to Montalcino. Sleep in Montalcino

After lunch, we'll come and pick you up to drive you to Montalcino. In the afternoon, you'll have time to visit the tiny historical center of Montalcino and explore the local crafts and products. A stop at the old town wine shop for a tasting of the superb wines of the area is highly recommended. But take it easy..we suggest you a good rest before tomorrow's hike !

Day 7 - From Montalcino to San Quirico D' Orcia, sleep in San Quirico

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..

Day 8 - San quirico to Pienza. Sleep in Pienza

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.

Day 9 - Pienza to Montepulciano. On route Monticchiello. Sleep 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.

Day 10 - Departure

While taking a nice cappuccino, let the memories of this Tour come back to your mind..then pack your baggage..we hope you enjoyed your stay !

Bus from Montepulciano to Siena or Montepulciano to Chiusi (trains to Rome)

Contact us for private transfers

In Greve

We choose hotel in the city centre like Hotel del Chianti or Hotel il Gallo

In Panzano

Panzano is very small, usually we use the B&B il Casello or similar

In Radda in Chianti

We choose Palazzo Leopoldo or Hotel San Niccolò

In Castellina in Chianti

We choose Hotel Salivolpi

In Siena

We choose Hotel Porta Romana or Hotel Italia or B&B quattro cantoni

In Montalcino

We choose hotel Dei Capitani or B&B

In San Quirico D' Orcia

We choose Hotel Palazzuolo or a B&B

In Pienza

We choose B&B Antica Locanda or B&B il Giglio

In Montepulciano

We choose La Terrazza di Montepulciano or a B&B