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Best Central Italy location for a weekly rental in late fall?

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We have been to Central Italy numerous times in spring, summer and early fall. This year we are thinking about trying it during a different season (late fall / winter). We love Cortona and have rented villas there previously. Besides Cortona, we are contemplating Florence (love it as well). The other place we're considering where we've never been is Bologna.

Given it will be off season, we don't want to stray too far from areas we know since we think you could fall into an area that's too quiet during this season versus on we have some familiarity.

We love restaurants and cooking and smaller towns. My thoughts as follows:

Cortona - great cooking spot and driving day trips

Florence - more central with a restaurant scene. Nice day trip options by train

Bologna - heard good things about the food there

Rome - bigger than we want

Appreciate any thoughts for a home base with good residential options (I'm a little high maintenance on accommodations so want a nice villa/apartment).

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