Surface matters!
I've done a lot of walking vacations and have realized that the surface I'm walking on matters hugely for the comfort of my feet. If hard concrete, like New York, cushioning. If uneven, like trails, support so that my foot's little muscles aren't gripping so hard all day long. Cobblestones, in between / both if possible. And changing up the combo of shoe/sock and insole helps, too! Finally, I take things to roll my feet on (squishy balls, marbles, tennis, etc.), to work the kinks out each night. Makes a huge difference!
But I think the others who pointed out training specificity are exactly right: you need to walk to get fit for walking. It doesn't matter so much for a trip lasting a couple of days, but for a walking-based vacation, silly as it sounds, training is a good idea. For me. YMMV.
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