Montepulciano – Montepulciano loop from Sinalunga

Montepulciano – Montepulciano loop from Sinalunga

Moderate

5.0

(1)

riders

Montepulciano – Montepulciano loop from Sinalunga

02:17

47.5km

600m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: November 2, 2026

Tips

The surface along some of this route may not be suitable

Some segments of your route comprise a surface that may not be suitable for your chosen sport.

After 20.2 km for 267 m

After 21.5 km for 268 m

After 21.9 km for 70 m

After 40.5 km for 269 m

Waypoints

Start point

Train Station

Get Directions

19.4 km

Climb to Montepulciano

Highlight • Climb

Gentle climb with wonderful views of the Tuscan hills. Montepulciano is worth a stop for a snack among the characteristic streets

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20.0 km

Church of St. Agnes

Highlight • Religious Site

Baroque and neo-Romanesque style church.
It was built in 1306 by the abbess of Poliziana Agnese. At the end of the seventeenth century it was radically renovated.

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20.4 km

Beautiful medieval village to visit. From the view of the vineyards to that of the Val d'Orcia, there is no shortage of views, not to mention the streets and alleys within the city walls. Unmissable Piazza Grande.

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21.5 km

Cathedral of Saint Mary of the Assumption (Montepulciano Cathedral)

Highlight • Religious Site

Place of worship and prayer

Piazza Grande, 53045 Montepulciano SI
montepulcianochiusipienza.it
057871951

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21.7 km

Town Hall of Montepulciano

Highlight • Historical Site

Overlooking Piazza Grande, the Palazzo Comunale is one of Montepulciano's symbolic buildings. Originally from the 13th century and reworked by Michelozzo in the 15th century, it echoes the forms of …

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21.9 km

Montepulciano

Highlight • Settlement

A high-altitude medieval and very well-preserved town. Despite the steep ascent, it is highly recommended and worth seeing. Even the view of the town on the approach is magnificent, and …

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23.7 km

Avenue of Remembrance

Highlight • Monument

Conceived as a monumental link between the Temple of S. Biagio and the Old Cemetery, it consists of two rows of cypresses arranged on the sides of the road. At …

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40.6 km

Town Hall (Former Pretorio Palace)

Highlight • Historical Site

It dates back to the 13th century, but numerous changes and renovations have been made to date. In 1266 it housed the administrative headquarters of the podestà in office at …

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47.5 km

End point

Train Station

Way Types & Surfaces

Way Types

27.1 km

17.8 km

2.71 km

Surfaces

45.4 km