So about these hills...

I did the Portugal tour in April.
I was expecting hills, and yes it's very hilly and often pretty steep. The killer for me was the surfaces of the walkways. Sometimes tile, but mostly 2" stone blocks. As a klutz, I found walking in the cities daunting.

Well Porto is basically a city built into a river gorge, so you can be at the top where it’s relatively flat but as you head down towards the river it’s going to be all uphill on the way back. The hills are very steep, and I live in a very hilly city myself. Plan your day to make sure you always end up at the bottom near the river, then take a taxi back up if the hills are going to be difficult for you to manage.

The killer for me was the surfaces of the walkways.

This has me worried as well. I'll be there at the end of March, so apparently I should expect rain. As of right now, I'm planning to take my hiking shoes, but while I know they're good on rocky hills, I'm not convinced they'll be good on slick, smooth hills where there's no traction. I've read rubber soled shoes might work better, but I haven't found any waterproof shoes with rubber soles so far.

I am going to Lisbon in February. I am concerned about the slickness underfoot, more than I am the steepness. I was in San Franciso recently; the hills were steep and I occasionally had to stop and catch my breath, but they weren't undoable for me. I walk in a somewhat hilly neighborhood and exercise regularly.

I have a pair of Allbirds Wool Runner Mizzles, which are water-repellant and which seem to have a pretty grippy sole. I haven't needed to wear them since I bought them, so I can't vouch, but I am planning to wear them on several upcoming trips, including Lisbon, and hope they'll provide the traction I need not to face plant.

I think San Francisco might be a good comparison. There aren’t a lot of hills that are the long hill like in Florence. But in certain areas of Lisbon and Porto, the hills are pretty much everywhere. Regarding shoes, I would say a good pair of sneakers with good grip. Remember, there are many many people who live and walk in these areas every day. That said, it is a bit more treacherous after it rains. The good news is that the cobblestones drain and dry very quickly after rain.

That's good to know Kathryn, thanks!

I can recommend these KEEN lightweight well-tredded waterproof hiking boots. I have them in the Canteen/Andorra color linked as well as a blue called Majolica/Tapestry and an older version in green. You can get them from a number of online vendors including Amazon. I particularly like this style because they are 100% textile and synthetic. I wouldn't get any that are leather due to the weight. I've found that their waterproof technology keeps my feet dry and comfortable all day long. They have multi-directional lugs in the rubber outsole that provide excellent traction.

I wear these boots on every trip, regardless of season or location. In combination with over the calf Sockwell moderate compression socks, they help to keep me from tripping or turning an ankle on rough terrain, as well as provide the support and circulation I need for long days of walking and standing. The older I get (I'm now 77), the better they seem to be for me, but I've been wearing them or very similar boots on trips for about 14 years. I have tried sneakers or more "fashionable" footwear on 3 trips during that time, the most recent being in 2017. All those attempts were major mistakes. 🥴

I can't recommend the red (Rhubarb/Jam) color. I tried those last summer and they were too narrow in spite of being medium width. It turned out that they were not made in the same country as my others.

KEEN has a newer version of this mid-height boot called Terradora Flex that's probably also worthy of consideration. I dare not try them. My shoe shelves are full.