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Ultimate and special Italy for a picky traveler

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Hello from the Asia Board. I'm based in Tokyo and can give you any secret insider tips for most anywhere in Asia. However for Italy, I could use your help with special recommendations. I'm looking for some special tips.

My husband and I will go to Italy (flying to Milan or Rome) for about 12 days in late April, early May this year. I've been to Italy several times before many years ago, but it's the first time for my husband.

For all you Italy fans, could you tell me your favorite cities and places, especially considering the season? I suppose we're mostly into food, wine, a cozy atmosphere, local culture and people watching, small independent funky boutiques and designers, fashion (but not famous designer brands) hip design shops, local hole in the wall type places, local food markets, walking around, beauty, relaxing. Not into crowded tourist places, famous sites, famous museums, etc. Not really any sightseeing needed. I like to learn about people's daily lives and typical culture. We're more into cities than countryside, but open to ideas. We often rent an apartment in Paris and would love to rent a place in Italy to hang out. Can't decide where to be based though or how many places we should visit. Too many options.

We're not sure how much time to spend in Milan, Florence, Venice, Rome, if any. Would like to rent a small cozy apartment in one of these places, hang out, and maybe take some day trips from there. Plan to have a lot of good food and wine and shop in unique and interesting little shops. Want to avoid very crowded and touristy areas and would love to soak up the local culture as much as possible. Any ideas?

Thanks in advance.

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