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Help me bookend our Bologna stay in December

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We have just booked Casa Letizia in Bologna for Dec. 21-29. We plan to enjoy Christmas there (we get our kids and grandkids on alternate years, so this is our Thanksgiving year), take a few of the obvious day trips, etc. I am pretty sure I will be able to add on another day or two if we decide to do that, but for now that seems like a good amount of time.

We are aiming for a total of about 18 nights, can go higher if necessary. One option we are toying with is flying into Milan and out of Venice (or vice versa) with 3-5 nights in each place. Then train for travel into and out of Bologna.

I am a bit overwhelmed by all the advice and options on lodging in Venice. I have taken many notes from the forum but would appreciate any advice on place to stay for us. I am leaning towards a B&B/hotel rather than an apt., but am open. I am also finding that some of the places that have been recommended here may be closed. Like Al Ponte Mocenigo, and some hotel whose name escapes me but that begins with a W and was recommended on a thread.

We are in our mid-late 60s, walk a LOT, travel with just carry-ons and like to use public transportation. Ease of arrival and departure is as important for us as proximity to the sites, because we walk so much that it doesn't matter to add on a few more minutes for our touring days. But avoiding the hassle of long trips from and to the train staion and/or airport is a benefit.

Are there other cities you would recommend for our two "stay put" segments?
Any good lodging recs for the places I'm toying with?

I got so much good help here with the Sicily trip we took last fall, and it did make us realize that our whirlwind travel of Italy from our youths needed to be replaced with a slower, more detailed enjoyment of some of these amazing places. Many thanks!

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