i will be staying in siena for the most part in the fall and i've heard about the cobblestone sidewalks which make walking in heels a nightmare. is this true? would i be asking for trouble if i bring 2 inch heels? thanks!

Almost all of Italy has cobblestoned streets and walkways. The Italian women seem to adroitly manage to handle walking in even the tallest of heels. My own "personal best" was a 2" heel, but it was also a pretty solid heel, not a stiletto. Proceed at your own risk.

BC

bookchick, I am proud of you! 2" heels!
I guess if they are thick enough not to get stuck in between cobblestones that would be fine. I haven't had the nerve yet.

I did have on some wedged mules and when I stepped up to get on a bus one of them fell off and I had to fight my way back down the steps to get it, that is my sad tale.

If you plan to walk a lot..then it's a no no But as I see, you are going to be there for a lot of time so maybe you have the chance to use them

Why do you want to put yourself at risk of straining an anckle while on vacation?

I bought a drawing from a very cute gal in Rome. I noticed her shoes right away and they were fabulous with about a 3" spike heel. I complimented her on her shoes ( I LOVE shoes) and she said she had broken the heel that day. Turned out she was Scottish and married to an Italian. Hmmmmm..do you think she broke it because she was NOT native Italian? Anyway, just wanted all to know that the "natives" are not immune.

I managed 2.5" stilettos for one night out but nearly broke my toe when my flip flop (no height) got stuck on a cobblestone in Pompeii... go figure ;-)

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As for Italian women navigating the cobblestones & hills (don't forget Siena is a HILL town), they live there & presumably, more used to trekking on the uneven surfaces. My days of high heels, even if only 2 inches are long gone. I wouldn't do it .... but you may be more adept than myself.

Once while strolling on one of the Cinque Terre paths (Manarola-Corniglia), I saw an older woman briskly walking on her way to the next town, and she was nicely dressed in heels & hose.

if u wear heels on a daily basis then it might not be that big an issue for you. You could if you have a large enough bag just throw a pack of flat shoes in, just in case you feel the need to wear them. Maybe walk round in your flats and change into your heels if you are stopping to eat etc.

Hi C108, I always wore highheels in Italy and never had a problem but I wore highheels everyday at home so I was very use to them.

On my last trip to Italy I started wearing flats and only wore highheels when going to dinner at restaurants.

If you are use to wearing highheels a lot you should be fine but probably you will want a pair of shoes for sightseeing that are not highheels.

Siena is especially bad for heels -- not only are there cobblestones, but really really steep sidewalks and really really worn stone steps. Save 'em for another city.

Realizing and apologizing in advance that this post isn't helpful or relevant - my husband claims there are 3 absolute truths about Italy. All food is good, all wine is good, and everything in Italy is uphill!
Best wishes in Siena!

I wear comfortable but fashionable shoes during the day (hate the look of tennis shoes). In the evening, I would wear my usual shoes but then carry a nice pair of heels in a cute bag and put them on for the evening out. It works for me. Yes, It is hard to walk on the cobbled streets in heels

Walking in high heels in Italian streets should be an Olympic sport. I will wear heels for a special evening if we are going by cab - and perhaps strolling a block or two - if I have a strong arm to lean on. Otherwise I stick to flats or low wedges.

The Italian women do it easily all the time - I can't imagine how - but suggest it would take months - if not years - to learn.

This thread regarding high heels makes me smile because as I said on my other post I always wore high heels in Italy without any problem. But the last trip I saved the high heels for dinners in restaurant.

But the reason I smile is that the only time I went "splat" on the pavement was in Milan. I was so busy looking up at something beautiful (do not remember what) and I was consequently not watching where I was going and oh my did I do a tumble! The funny thing is that it was one of the few days that trip that I had flats on. I did have some very handsome gentlemen assist me though, LOL.