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Looking for Tour in Italy

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I am looking for a tour for Italy. Many of you helped me plan my "mom memorial tour" back in March. But now my stepdad would like to go back to Italy. He has been many many times (From the Lake Country and through Sicily) but this would be the first time without my mom, so he would like a tour (about two weeks).
1. He was going to go with his alumni group at Brown University but the trip is three weeks--too long.
2. He loves art history and HATES shopping. Just enjoys looking at art and eating. So a tour group that may be geared toward that. Trying to force him to try a cooking class for a day or two because he doesn't know how to cook for himself now.
3. It would be great if it is not a super big group but also where he may meet others travelling alone and maybe other widows or widowers.
4. For this fall: Rome and Florence and? (he says Venice and I am talking him out of it.... it was way more crowded and touristy than he remembers but OK maybe Venice).

Any ideas for tour that might fit that group? Leave from NYC?

Thanks for any ideas.....

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