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Bologna - San Marino/Florence/Siena?

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I have been to Florence but never to Bologna, Siena or San Marino. I am thinking of spending four nights in the area in December (I know not the best time of year to be in Tuscany). I would base myself in Bologna and travel to each city as a day trip to avoid schlepping my luggage around and so that I keep my schedule a little flexible in case the weather isn't cooperating (I've read what the walks are like in San Marino and would like to the city on a rainy day). As many things in Italy are closed on Sunday, I plan on flying to the country on Sunday (from within Europe so jet lag isn't an issue), and will have Monday, Tuesday and Wednesday to see the sights. I have no intention of going back to the Uffizi or Academia in Florence, but would like to stroll around the city's historic centre.

Is Bologna a good base for visiting these cities? My flights would be in/out of Bologna airport - I've checked flight schedules an open jaw flight isn't possible.

As I'd like to keep my schedule flexible, I don't plan on purchasing train tickets in advance. Is there a Tuscany train pass that would work well for this trip? Any other ways to avoid paying full price for train tickets?

Any information on the destinations will be appreciated.

Thank you.

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