Yes, barefoot jumproping really helps strengthen your feet and can toughen your soles as well. I have four jumpropes but seldom use them any more since I discovered I can do the same jumping just about anywhere, anytime, by just imagining I'm swinging the rope, moving my hands and feet the same way. Virtual jumproping, try it.
I also walk barefoot on my rolled gravel-over-tar road on most days, usually no more than a mile and a half barefoot before I put on shoes; the gravel is consistent in size and sharpness so no cuts. I otherwise walk and hike anywhere with thin-sole Merrell Trail Gloves. Similar to Five Fingers but there's no separation of toes, which I prefer. If toes rub, Body Glide or vaseline stops chafing. Loved the Trail Gloves so much I bought a second pair for when these wear out.. Didn't try the Vapor Glove model.
I don't run, except for short spurts on grass -- I walk a lot though, and am always heel-striking. And I'm suspicious about hiking trails barefoot because of unknown sharp pebbles, such as in my relative's driveway, and sometimes my own. I can't imagine doing it in the shale gorge near me. A cut in my sole would set me back. Perhaps with enough time and practice my sole could get as thick and tough as a baseball glove, but I'm not going to find out. No need to. I feel the rocks and other surfaces well with the Trail Gloves. I also walk sometimes with the wide toebox Altra Lone Peaks, which are spongy zero drop, and the Altra wide toebox zero drop Olympus shoes with maximum cushioning, although I'll probably give those away. Feels like I'm walking on a thick layer of ensolite. Three heavy people I know who asked about my Olympus shoes months ago bought them and then told me they relly like that extra sponginess for daily use. We're all different.
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