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Best Days to Visit or Avoid Cities on Our Itinerary

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We will be buying tickets for our trip to Italy in May 2014 soon! We have planned a tentative itinerary, but before we decide which day to arrive, I thought I would ask those of you who have been there if there are certain days of the week we should try to be in a particular city (because it's less crowded, there are market days or other special events, etc) or avoid being there (because of larger crowds, the museums are closed, there will be a special festival/event in town that will make it uncomfortably crowded, hotel prices will be higher, etc).

Also, will any time in May be about the same in terms of crowds and hotel/apartment prices, or does it get progressively more crowded, more expensive, etc as the month goes on? We live in a very hot climate and would prefer to be there before the weather gets hot , although we know that's unpredictable.

We plan to use public transportation if that makes a difference.

Current Itinerary
Fly into Milan
Lake Como (stay in Varenna or Bellagio)
Venice
Ravenna (maybe)
Florence (with side trips to Lucca, Pisa, Siena)
Cinque Terre (maybe)
Orvieto (maybe)
Rome
Depart Rome

Would Siena be visited most easily as a day trip from Florence, or as a stop on the way to Rome?

Comments on Varenna would be appreciated. I added it to the list as a "possible" primarily because I read that the Byzantine mosaics at the church there are among the best in the world.

We would also appreciate comments on visiting Cinque Terre. We are an older couple and my knees make climbing stairs and steep hiking difficult, so we are unsure whether we would be able to really experience its charms or should plan to use those days to visit other towns in Tuscany or Umbria.

Thanks in advance for your expertise!

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