Best trekking walks Siena

If you ever wanted to go trekking on country roads, surrounded by nature, then the countryside near Siena may offer you the perfect opportunity to achive this desire.

Among all the trekking roads you can follow, we suggest you Via delle Grance, which is one of the ancient roads followed by pilgrims, like the famous Francigena (an ancient road that goes from Rome to Canterbury, crossing France). It offers the opportunity to enjoy the quiet and colorful nature, but also to visit typical historical buildings of tuscan landscape. All the grance (ancient fortified medieval warehouse used to store wheat) you may see on this track, belonged to the hospital Santa Maria della Scala, which is opposite to the Cathedral of Siena. In the Middle Ages this hospital used to help the poor and worked as an orphanage too. The hospital staircase symbol is still on all the buildings related to it in Val d’Orcia.

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Grancia of Cuna- trekking walk through Crete

The trekking trail is divided into 6 stops, and goes through the amazing Crete Senesi and Val d’Orcia. Almost entirely on coutry roads it will bring you in medieval towns but also across the wild nature side of the tuscan country. It is recommended to buy a map of the Crete Senesi and Val d’Orcia before start trekking.

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Val d’Orcia, trekking (photo credit Gianluca)


1°Stop– from Siena to Monteroni d’Arbia:  Time: 6h-3.30h / Length: 20km-12km

On this part of the track you won’t find a significant difference in altitude. You may choose to start your trip from the Cathedral Square in Siena and visit the hospital, or from Malamerenda, a little town near Siena, where all the tracks start.

TRACKS: 502-500

2° Stop- From Monteroni d’Arbia to Asciano: Time: 5.30h / Length: 16km

This part is pretty long, but not too hard, even or casual walkers. Moreover it goes across the Crete Senesi, which is a particularly clayey soil, that’s why it is adviseble not to walk on this part of the itinerary when it rains.


3° Stop-From Asciano to Belsedere’s Farm: Time: 5.30h / Length: 18km

This part is long too, but you may stop in Serra di Rapolano, which is a typical medieval hilltop town. The landscape in this part of the route is the most incredible of them all.

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Country near Siena, sunset-trekking (photo credit Antonio Cinotti)


4° Stop- From Belsedere’s Farm to Sant’Anna in Camprena: Time: 4h / Length: 13km

The difference of altitude gets higher, remember you’re still on clayey soil. Here you are trekking into the wild side but you will also find two medieval towns on the track, which offer a breathtaking view.

TRACKS: 516-517-517a-566

5° Stop- From Sant’Anna in Camprena to San Quirico d’Orcia: Time: 4.30h(2.30h) / Length: 15.5km(8km)

The difference of altitude gets lower again. Should you wish to cut the paved road part of this itinerary, then you may take the Postalino di Val d’Orcia (a private bus).


6° Stop- From San Quirico d’Orcia to Castelluccio: Time: 6h / Length: 19km

This is the easiest, but longest, part of the track. Panoramic views and ancient buildings are characteristic features of this part of the itinerary. Part of the track here has no signs so hold on to your map!



The numbering list of the tracks refers to the map of the Crete Senesi based on the paths of CAI (Italian Alpine Club).

Our location:

Borgo Grondaie would recommend you to divide this itinerary in daily stops. Our position it’s one of the strategic points from where you can start your daily explorations. Moreover we offer parking, where you may leave your car, and a salt water pool where you can relax. Check our new offers on our website:

Borgo Grondaie Siena Hotel and Apartments

Edit by Borgo Grondaie




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