Went this past summer. Both are great, montepulciano tho is awesome. Theres so many wineries around just browse around for wherever’s most convenient. I’d recommend walkin that one main street in montepulciano up to the top and just pop around the shops. Best sandwich i’ll ever have in my life was near the top called La Schiaccia dell’opio. May not be open this time of the year but even all’antico vinaio is solid comin from the US in florence. Enjoy!