Anonymous wrote:I find Vejas uncomfortable and prefer adidas Stan Smith. Ideally in a style made of grained leather, not the smooth ones. They are softer. Sambas are cute too, but it might be too rainy for suede (not sure which style you're eyeing).
Not exactly what you're asking, but regardless of the sneaker, orthotics help so much. Doesn't have to be custom. I went to a running store to get a pair for my arch type. They take a little bit of time to break in, so getting some now would be perfect for your trip. They're the reason I can walk 10 miles in flat sneakers without any issues.
That's a great solution, I'll need to try that myself. Op, my advice was going to be stay away from flat bottom tennis shoes but this solves one issue, comfort, but you also want good traction. I wanted cute sneakers too but all the walking required something more like running/walking shoes even though it's not going to look that great, at least you'll be able to forge on. There are some well worn stairwells and unpaved steep areas you'll want a good grip ESPECIALLY in Italy