Designed for history and art enthusiasts, the itinerary winds through the scenic roads between vineyards full of sites of cultural interest, all to be discovered.

First we encounter Castello Masegra, the only military structure in Sondrio of medieval origin to have remained intact to the present day, which, since 2019, has been home to CAST - the Castle of Mountain Stories, a 'storytelling museum' that has opened a new chapter for the historic site in Valtellina.

Along the scenic route among the vineyards it is possible to visit Castello de Piro al Grumello, a rare example of a twin castle built in the late 13th and early 14th centuries in a strategic position on the sunny slope.

Continuing on, in the locality of Montagna in Valtellina we find a church complex composed of religious buildings from different eras: the 15th-century Church of San Giorgio, with 15th-16th-century frescoes; the Oratory of the Madonna del Carmine (15th century), with a cycle of Renaissance frescoes by Sigismondo de Magistris (1515); and the Church of the Beata Vergine Addolorata with 18th-century paintings inside.

In the locality of Poggiridenti, on the other hand, it is possible to visit the Church of San Fedele, which preserves valuable 18th-century artifacts and a 16th-century chapel preserving a large fresco painted by Fermo Stella (1528).

On the way back, a stop at Bosco dei Bordighi, a nature reserve rich in wildlife and tree diversity that covers 47 hectares, is a must.