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Any interesting, offbeat (and BRIEF) tours?

My girlfriend and I went to Germany last year and we took the Night Watchman tour in Rothenburg ob der Tauber and we loved it. Everything about it was unusual; it was immersive and the guide is in character, it was educational while still managing to be light-hearted, and it took about an hour from start to finish. We really had a great time.

My question is has anyone taken any tours in Italy that are in that same spirit? We're going to be in Italy during winter, 2016/2017 from december 23 through January 11 and our plan is to go from Milan to Tuscany then Rome, Amalfi, and on to Calabria, where my gf's family originates and then we'll finish it out by heading from Calabria to Valle d'Aosta and snowboarding until it's time to go. The way we have it structured - for now - there's a lot of room built in for changing plans.

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Let me say, also, that any suggestions for things to do and see will be appreciated. She's 27 and I'm 37. We both like going to bars and clubs, dancing, shopping...etc. I realize Italy's supposed to be relatively dreary in winter, so I'm not anticipating doing too many outdoors activities other than snowboarding, but any suggestions for outdoorsy stuff in Calabria or the Sorento/Amalfi/Pompeii area would be great.

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