A rugged, multi-purpose shoe for Sicily and Campania?

For years my standard travel shoe was the Timberland Stormbuck Oxford. I was bummed last year when it was discontinued, but found a close replacement with the Redwood Falls chukka boot, which is waterproof, has a moderately aggressive lugged sole, and excellent support. With long pants it passes as an oxford/casual dress shoe. I've worn them for two week trips to both Italy and Poland:

https://www.timberland.com/en-us/p/men/footwear-10039/mens-redwood-falls-waterproof-chukka-boot-TB1A44MGV13

I see that they have now added two new oxfords, both waterproof and with a lugged sole - here is one of them:

https://www.timberland.com/en-us/p/footwear-0100/mens-britton-road-lace-up-waterproof-shoe-TB0A69T9W01

For casual hiking, stomping around ruins, but also for urban strolling, one of these style may fill the bill. They are incredibly long wearing. Note that it appears that my new chukka boots have a steel shank inside - I had to remove them even for TSA pre-check at LAX. But a small price to pay.

Look at Oboz

Instead of limiting yourself to only one pair of shoes, you may want to consider your preferred walking shoes and then get a pair of ballet flats like Tieks for dinner or church. Yes, I know, technically two pair of shoes; however, ballet flats when packed flat take up negligible room. While touring, I have put Tieks in my day bag to change into if needed, with the provided reusable bag to place my Hokas into for the footwear change.

On our first trip European trip several years ago I agonized about shoes and then decided if my feet went down, our vacation would go down with them. It was an early summer trip, so my compromise was a good pair of walking shoes (Hoka for me) and Rieker sandals. Some days I put 10 miles or more on the Hokas. I could walk about 5 miles on the Rieker sandals, but could not wear the sandals 2 days in row and walk 5 miles both days. On the days I wore the sandals, it was all city walking; no trails.

We have travelled up and down the boot in Italy and are booked for Sicily next year. It has been our experience as long you as you are nice, try a little Italian, and are respectfully dressed for the setting (shoulders and knees covered in church), the Italian people treated us wonderfully, with little regard for our shoes.

Just for clarification, because it must not have been clear from the original post, this is a question about men's footwear. I agree that ballet flats fit the bill for a woman, but they don't fit me.

Yikes! Sorry about that...

We each pack in a carry-on suitcase and a backpack. When we travel to Europe we are there for at least 3 weeks and my husband wears a 12-Xwide shoe. He brings 2 pairs of shoes; he wears a pair and packs a pair. We typically put one shoe in the suitcase and one in the backpack. I slip each shoe in a plastic grocery bag and then loosen the laces, "lining" the inside of the shoe with another grocery bag; we then fill up the shoe with socks, underwear, deodorant, etc. whatever will fit. He typically wears Hokas and then packs a pair of Rockport oxfords that are water-resistant/proof that can be worn inside or on trails. While they would not be his first choice for church at home, he has worn them inside churches and restaurants in Europe no problem. The boots you have linked, to us, would be fine.

Our next trip includes Paris, Milan, Sicily, Rome and Naples, and this is how we will pack for the trip.