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11-12 days between Bologna and Rome - ideas please!

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It is possible that this trip may not happen, [DH not showing his customary enthusiasm, for some reason] but in the back of my mind and moving towards the front I have the following plan:

fly into Bologna [two reasons - I've never been and Ryanair have really cheap flights there out of Bristol], stay 2-3 nights, then work out way over to the Tyrrhenian [west] coast ending in Orbetello or Porto Ercole before flying home from Rome on Easyjet 12 days later.

my main question is where to stay between Bologna and Orbetello - looking at the map, we can choose between the obvious route which would skirt Florence [which I've no desire to return to on a driving holiday] or to take what looks like a more interesting route via Ravenna, Arezzo, Cortona?, and Pitigliano.

not having stayed at any of these places, I've no idea which would make the best bases, and how long to stay in each. we would be travelling in about a month's time, pre-booking the first 2 nights and possibly the last 2, but otherwise just seeing where we end up. On the whole we like to spend our nights in towns where there are shops and sights to see and we can walk to a new restaurant every night and drink a bottle of wine without worrying about driving.

Thank you in advance for any thoughts you may care to share.

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