I was in Tuscany just in last fall. Here’s a travelogue of the places we went to:
Tl;dr - Montenidoli in San Gimignano is an extremely memorable place and totally worth the visit.
In Chianti Classico visits to Poggerino, Val delle Corti and Carleone are well worth it
When we were in Montalcino, Coste del Vivo was a terrific alternative to big name Brunellos
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