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Driving through Chianti on Halloween - where to stop for lunch?

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My Mom and I will be vacationing in Italy this year (my second trip - her first!) We'll have about 15 days at the end of October, beginning of November to enjoy ourselves - it's looking like this:

Land in Milan - train to Cinque Terre - 3 nights in CT apartment
Train to Florence (with a stop in Pisa on the way - Mom really wants to see the tower and a few other sights in Pisa) - 4 nights in Florence B&B
Rent car and drive to Podere Lucignano Secondo Agriturismo outside of Siena - 5 nights at agriturismo
Drop car at Orvieto and train to Rome - 3 nights in Rome (Trastevere) apartment
Fly out of Rome

I may have other questions later, but I just realized that we'll be driving from Florence to the agriturismo on Halloween. I'm assuming that this should be okay and that generally the towns through Chianti will be open for business - I know Halloween is not as big of a deal as All Saints on the following day in Italy (though I was in Rome on Halloween a few years ago and the kids were valiantly trying to get folks into the swing of things!) Anyone know if I'm wrong about this?

I'd like to take the scenic route through Chianti and stop somewhere for lunch and some sightseeing - we've got about 5-1/2 to 6 hours between the time we pick up the car and the earliest we can check into the agriturisimo. I would really like to stop in Castellina after lunch and before we head to the Podere (I am unashamed to say that I'm am dying to stop at the gelateria in Castellina). But if we picked one other place in Chianti to stop before that - what would you recommend? I'm not opposed to a winery, though I'll do no more than taste (I'll be driving), but that doesn't mean Mom can't enjoy! Or some shopping, pleasant strolls and a leisurely lunch in a place with character or/and a view would work as well. (FYI - my Mom is a very young 72 - she is very active and a lot of fun. No mobility or health issues - she just might be in better health than I am!)

Looking forward to your recommendations!

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