Packing is not one of my favorite things about travel, but it is a necessary evil. For this trip, we are each limited to one piece of checked luggage with a maximum weight of 50 lbs.
Weather and planned activites are important considerations, as is comfort. Historical temperatures in Sorrento and Rome for the third week of October are in the high 60's during the day and the low to mid 50's at night. It may be a little warmer some days and a little cooler some nights, but this is the typical range.
Comfortable shoes are a "must have" as we will be doing a fair amount of walking, some of it on uneven surfaces (especially at Pompei).
A bathing suit could come in handy ... the rooftop pool at our hotel in Sorrento will still be open, as will the hot tubs.
Jackets for gentlemen are not required at dinner at the hotel, but they would not be out of place either. If you are planning to go out for a special dinner on Saturday night in Rome, finer restaurants in the capital will expect jackets.
I've received lots of advice over the years, from exhaustive lists of everything I might think about bringing along, to instructions on how to travel with nothing more than a backpack for a month.
Neither of these options work for me.
However, here are some articles and web sites on the issue that may be of interest:
Notes by Chris Gray Faust, the former travel editor at USA TODAY
One Bag, a website with packing light tips
Slowtrav's exhaustive list of things you might think about taking
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