There is good parking for cars or campervans near the Church of San Biagio. Starting your hike here is a good option (and the directions of our gpx file). If you prefer to start this itinerary from Montepulciano’s Piazza Grande, enter the city through the main street of Montepulciano, the Via di Gracciano nel Corso which stretches for 11.5 kilometers from the Porta al Prato to the Piazza Grande at the top of the hill.

One of the highest of the Tuscan hill-towns, Montepulciano is built along a narrow tufa ridge, with a long main street and alleys that drop away to the walls. The Piazza Grande is built on the highest point of the ridge.
Start in Montepulciano’s Piazza Grande and take the panoramic path to Porta dei Grassi, where you will encounter the Tempio di San Biagio. Then take the Via dei Canneti until you reach the intersection with Via delle Colombelle. The path follows the mountain ridge and leads you through the Nobile vineyards to the oratory of Sant'Anna in Via dei Colli, in the foothills of Montefollonico. Stop in Montefollonico for lunch.
This track also passes the wonderful ruins of the Monastero di Santa Maria, and the magic picnic spot of Il Tondo, east of Montefollonico.

[You can discover Il Tondo and walk around the hill. For this extended itinerary download Montepulciano-Montefollonico (Il Tondo).gpx]

From Il Tondo walk down following Via dei Frati towards Montefollonico (you walk around Residence Sangismondo), then left on Via dei Frati and again left on Via dei Giglio. On Via dei Pianelli you can enter the old center of Montefollonico climbing the stairs in front of you, or walk towards Bar Sport (to the right).
Bar Sport on Via Pianelli is a good spot for a coffee or a refreshing drink. Here the locals watch tourists passing by. In front of Bar Sport, you can enter the historical medieval center of Montefollonico through Porta del Pianello. A lunch in one of the two excellent restaurants (Ristorante La Chiusa and Osteria La Botte Piena) in Montefollonico is recommended.

Approximate distance: 17 km -
Time: 3,5 hours

Total climb 651 m | Total descent 542 m

Sanctuary of the Madonna di San Biagio

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Photographic impressions | Montepulciano / Walking Back To Montefollonico

Podere Santa Pia is a beautiful, stately stone farmhouse that blends the best of Tuscan charm with all the beauty and comfort of refined Italian taste. This unique holiday house, set a stunning location surrounded by nature, can host up to eleven guests. The house is surrounded by a lovely wild garden, tall cypress trees line the property and hidden in a nearby corner is the large swimming pool overlooking the rolling hills of the Tuscan Maremma.

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