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Milan at the end of September

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So I am lucky enough to have a friend let me crash at her place in Milan from September 20-September 29. In speaking with her and some others who have been to that region of Italy, I think that two solid days in Milan to see the Duomo, canals, Galleria, La Scala, etc would be sufficient. Basically, the trip will consist of "day trips" out to nearby areas.

We are definitely going to Verona and perhaps Garda while there...

Lake Como or Lake Maggiore?

Brescia or Bergamo?

Mantua? (I read something about being known for Pumpkins.) Cremona? (Stradivarius violins town) Worth visiting?

Should I try to get to Venice, Genoa or Turin?

How many days do you think for Cinque Terre? And where on the coast do you recommend?

Also, do you think it is worthwhile to take an organized tour to these areas or just wing it myself? I'd prefer to have some sort of plan and book things accordingly...less to have to do while there!

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