We spent two weeks in Italy in October this year.
I bought a few different pairs of shoes leading up to the trip and ultimately decided to bring two pairs:
One pair of brown leather sneakers by Ecco and a pair of walnut brogue wingtips by Allen Edmonds.
The wingtips were from the "Road Warrior" series by Allen Edmonds. When packing for the trip, both pairs of shoes were still very new and a little stiff. I thought I'd wear the sneakers during the day and wear the dress shoes in the evenings.
As it turns out, I was completely wrong. After the first week of our two-week trip, I put the sneakers back in my suitcase and wore the dress shoes exclusively. Even when walking several miles a day, they were far more comfortable than the sneakers I brought.
I have other, more expensive, dress shoes from Allen Edmonds, but none of them are as comfortable as those in the Road Warrior collection. If you like dressing nice when you travel, give them a try. Your feet will thank you!!