My husband and I live in Chicago, and people often visit us. We love our city and spend a lot of time planning activites for guests. I can't tell you many times we had to scrap our plans because someone was wearing lame shoes that look nice but you coundn't walk more than a couple of blocks in them.
I'm probably preaching to the choir here, but please, please don't go all the way to Europe without a decent pair of walking shoes. And if it's cold, bring a hat, gloves, scarf and long underwear.
I agree, good comfortable shoes are the most essential thing. When travelling, you have to walk more than you can ever imagine doing at home, unless you are a marathon walker. If you can't walk without pain, you can't do much.
Agree all those cobble stones are a killer. Really comfy shoes are a must. I usually take at least 2 or 3 pairs so I can alternate them. That way I don't have any problems with them causing blisters.
My husband and I (we're in our late 50's) just returned from 3 weeks in France and can't agree more about ensuring you bring good walking shoes. We spent 1 week in Paris, 1 week in Languedoc and 1 week in Provence, walking through cities, country side, museums, cathedrals, etc. I brought a total of 3 pairs of black shoes that were absolutely fabulous: 1 pair of leather Merrill slip-on crocs (with a full back); 1 pair of Echo tie shoes; and 1 pair of Naot sandals (cork bottom). I was thrilled with all of these -- and I have bad feet! Not only were they comfortable but they all looked great. I packed light (1 carryon bag and 1 "tote" bag) so I was able to look and feel great with these 3 pair of shoes.
Good shoes, not necessarily very expensive ones that really fit are the key along with really good inserts. Shoes are mass produced and can be customized with GOOD inserts. I think my day hikers were o/a $70 bucks and the inserts where o/a $48. I can walk all day without tired tooties! Tired legs maybe.... Instead of long underwear I bring rainpants (from REI in my case). They have zippers at the ankle so you can slip them on over your regular pants/shoes. Two layers and toasty warm. Slip off eaisly indoors so you don't overheat.
Having an emergency moleskine on hand has bailed me out on many an occaision. I never travel without one.
Maybe I'm just weird, but I bought very nice, very expensive walking shoes for Europe, though I still had to bring some heels for the nighttime. Since I walk in heels daily to, from and at work, my feet preferred them to the walking shoes during the day on the cobblestone. I eventually just left my walking shoes behind and bought some wedges while over in Europe. Went the whole month and had no problems. I say go with what your feet are used to and most comfortable in.
There is a fine line between broken in and worn out. I think that it's better to have an older pair of shoes than a new one you aren't used to.
I also want to post about how your feet can and do swell with air travel and heat. I was in my sandals most of our trip this summer because my "wonderful walking shoes" were like sharp knives on my heels.
We almost skipped the Sforza Castle in Milan because the thought of walking that extra block was too much.
Fortunately at that moment we passed a Geox store and wouldn't you know, they were having a sale! Italy is so great!