For my spring trip to Italy, the thing I was most grateful I had packed were my waterproof boots. The Waterproof/water resistance is really important because even when it’s stopped raining, the cobblestones trap water for some time after. I recommend any neutral color, though I’m personally partial to white/beige boots. I thought they would get dirty a couple of days in, but they held up really well and still look new half a year later. I’m linking the pair I bought, along with other options if you want a slightly higher heel. I had NO break-in time with this pair and although I walked 25K steps daily, my feet honestly didn’t hurt. Check them out! LTKPetite LTKFindsUnder100 LTKOver40