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Florence Day Trip to Sienna: should we stop along the way? Where?

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We are considering taking a day trip from Florence to Sienna by car. We want to drive down to Sienna through Chianti. It looks like it's a fairly longish drive and we thought it might be nice to stop somewhere along the way, either for lunch of just a driving break. Google maps says the drive is only about an hour and 40 minutes or so, but we will almost certainly get a bit turned around, and we want to take it slow, so it'll probably take us considerably longer than that.

So we're thinking of taking the SS222 on the way down. Would it be worth it and/or doable to stop somewhere like Greve or Castellina along the way? Or do you think we wouldn't have enough time?

We are early risers and are ok with a very long day. While we are definitely interested in seeing Siena (one of us in particular is studying medieval history at university toward his PhD starting in September), we really want to enjoy the ride to and from Siena as well. My other friend and I are more interested in seeing the Tuscan countryside and small towns. Basically, we want the best of both worlds for this day trip.

So, do you think we need to drive straight to Sienna and give it as much of our day as possible, or do you think it's possible for us to enjoy it in an afternoon and maybe take a detour along the way?

Any suggestions?

Any suggestions or advice?

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