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Walking Shoes for Southern Italy- Puglia, Amalfi Coast, Matera etc

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Our trip to Puglia and the Amfalfi Coast is fast approaching- my hubs and I both need to shop for walking suitable walking shoes while we still have time to break them in. Suggestions? I searched and found some old topics on the subject. Last trip, I brought a good pair of Ecco Mary Jane-style walking shoes, which worked out great for casual and transitioned for dress, but the soles were thin and I could actually feel the cobblestones through them. Assuming the weather will still be warm during September, my casual boots may not be needed, and are perhaps be too heavy to pack, but I could wear them for the flight. Is September weather cool enough for boots? Also, we're staying in a cave hotel, so not sure if flip flops will work for navigating the floors. Input welcomed for both the hubs and I.
Thanks

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