Like you, I am always in search of cute shoes for serious walking. Although I do not have arthritis, I do have back problems, bunions and flat feet, so finding proper shoes is a challenge. Be sure to purchase shoes well in advance of your trip and wear them a lot before you go....You have plenty of time to find a brand/style that is comfortable and still cute enough for your needs. For a while, I was buying ugly, almost orthopedic shoes at "serious" shoe stores. Soon after, I realized I could still wear cute shoes, as long as they are of excellent quality and have the features needed for my problematic feet. Here are some of my favorites, worth considering for your situation. All are sturdy, quality brands appropriate for cobblestones and are popular in the U.S. and in Europe....Mephisto All-rounders (Less expensive than other Mephistos, as they are made in Asia instead of France)...I have purchased their various Mary Jane styles many times and found them to be very comfortable, even on cobblestones. My favorite style is the Nero, which is a combination walking shoe/sneaker/Mary Jane. I usually buy neutral colors like black or beige. However, they are available in a variety of colors, if you want something more flashy; Keens: Most of their sandals are good because you can wash them in the sink (or washing machine) and air-dry them if you find yourself in a muddy or funky situation. We just got back from an extended trip to Asia & Middle East....Some of the public bathrooms were very funky, so I was glad to have washable shoes!! Keens varied styles are just clumsy enough to be cute. Again, they are available in many colors; Dr. Martens....There are so many styles, some cuter and/or more suitable for your needs than others. My only reservation here is that some Doc Martens are very heavy. However, they are very sturdy and last a long time. I own several styles, some of which are quite clumsy (but cute), others more petite. One pair is 20 years old...They have been in rain up to my knees and survived the ordeal. They still look new! I have also had success with several Clarks styles, although I am not sure if they are quite substantial enough for your needs. I even wore Clarks ballet flats on recent trips and found them to be very comfortable. My husband (and many others) love Eccos for serious walking. I have never found any that are comfortable enough for my feet, but you might want to investigate these, too. My advice is that, even for a relatively short trip, you should bring more than one pair of shoes in a couple of different styles, to give your feet a rest and in case you have to deal with rain or mud. I suggest you go on line, look up the shoes I mentioned, study their features and read customer feedback, then go shopping. Many of these are available on line, although I would hesitate to purchase a style on line I had not already tried on in a store. Although Zappos.com has a very liberal return/exchange policy, they do not always have a full range of colors or sizes. Good luck with your shopping. I hope you find just the right shoes for your trip to beautiful Italy. Be sure to get reservations for the Academia, so you can see the famous "David"...It is breathtaking!