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14 days in Italy with a Classics Major!

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I am in the process of planning a 14 day sons and mothers trip to Italy with my son, his friend and his mother. My son is a classics major and is doing this as a summer study, of sorts.We are tagging along on his pilgrimage which includes many of the major sites of Italy but a few odd ones. Landing in Milan. Should we stay the night in Milan or go directly to Garda for two nights, skipping night in Milan. Desire to visit Catullus' villa in Sirmione, night in Venice, then Florence for three nights with a stop in Ravenna, then onto Naples for museums et al and Pompeii, Paestum and Herculaeum. We (moms) would like to savor the Amalfi coastline a bit. We have 4 days in this area. Then onto Rome for three full days, fly out of Rome.
I have been obsessively poring Fodors, Reid's, Frommers, for best hotels. Moderate budget. Even willing to try a monastary stay in one major city so we could splurge on the southern coast.
Please help. Do I need an agent to schedule transfers? I am most worried about that. Please offer any sage advice for these first time Italy travellers!

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