Here is the dilemma. My wife and I (average age, late 50s) will be in Italy for over a bit three weeks in October. Plan is to take just two rolling carry-ons, plus a couple collapsible duffels to use as carry-ons on the way back (checking the carry-ons, so that we can buy a few things in Italy).
We have access to washing machines everywhere we stay (Venice, Florence, Sorrento, Rome), so plan to rotate wardrobe.
But (and here is where la bella figura comes in), I am kind of at a loss on what to take. A sport jacket? Oxford style shirts? Shoes comfortable for walking 10 miles a day or so might not be dressy enough. With limited space, these are tough calls. Probably every bit as bad for my wife (or worse). So, ladies and gents, what do you recommend?
Note: Another possibility we have discussed is taking one larger rolling bag, which would be checked. But personally, I do not look forward to lugging bags on and off of trains and hope that can be avoided with some smart packing choices.