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Venice, Tuscany and CT in October

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Hello,
My friend and I are travelling to Italy - first time for me - in the first week of Oct. A 12 day trip. We are flying into Milan, planning to train to Venice for 4 nights, - rent an apt? - then train to Florence, pick up a car and at this point probably travel to Ameglia to a small villa rental we found so that we can use that as a base between Tuscany and CT, for 5 nights, then drop the car maybe in La Spezia and train to Milan for the last night before we fly out at 10 the next morning. Would recommend any thoughts or recommendations. Up for the Venice experience, sadly not going to spend time in Florence this time as my friend was there for a good stay before; in Tuscany, looking to see Lucca, and start researching a nice path through the area for a day trip or two...CT and also portofino...hoping to hire or go by boat to the villages. Won't be doing much hiking as my friend just had surgery on knee. She'll be in good shape, but probably not for any lengthy hikes or walks.
Thanks for any thoughts, the biggest adventure will probably me packing only in a carry-on, but I'm determined.

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