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What clothing diversity is needed when spending Oct in Veneto/Tuscany?

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I'm trying to pack a "manageable" amount of clothing and shoes for our stay in Verona, Venice, Florence and Monteriggioni, arriving October 1st and departing October 27th. I'll be watching the long range weather forecast in late September but that will only give me the first half of our time in Italy.

I'd like an idea if I'll get more use out of sandals or leather ankle boots, sleeveless tops and skirts or long sleeve sweaters and leggings. I'll take my rain coat but wondering if I'll need gloves and silk long underwear also. I plan to layer clothing but I'm not sure how drastically different those layers should be for comfort.

I know the weather varies from year to year within the same month and I even made a copy of the actual daily temps for Oct 2011 in Venice and Florence for a reference. I thought I had a good idea of what to pack but then I saw photos of a trip report taken the last half of Oct 2009 in Rome and it showed people wearing winter jackets, hats, gloves and red noses and everyone looking cold!!

I guess I didn't expect there to be much of a difference in weather conditions between the beginning and end of October. I wish I could afford a personal porter to carry my luggage between locations so I could pack for the extremes and everything in between ;;) That won't be happening so I'd appreciate your comments whether I should be considering more light weight or heavy weight clothing and footwear for October. Thanks, Deborah

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