From the first day I arrived in Cape Verde, I had blisters on my feet that prevented me from keeping my shoes on. At the slightest step, and even putting on my sneakers, I was in pain. So I bought flip-flops because I didn't bring any with me. Two days later, I had a week-long hike in Santo Antão. I asked the guide if he thought I would be able to hike in flip-flops and he replied that this is what most Cape Verdeans do. I was not confident at all but I went ahead, armed with my flip-flops and socks (because the new flip-flops were rubbing on my skin). Result: the hike was wonderful and walking with rather easy. However, the cobblestones leaned a little on the soles of my feet, but a doctor from the group created beautiful padded soles with compresses and sparadra. I also climbed Fogo's volcano in flip-flops. It took me two pairs of socks to get there because the pozzolana was so abrasive. Morality: if you have a shoe problem, there is always a solution within reach. I can't advise you enough to choose your good hiking boots instead of flip-flops. If you ask yourself the question of feasibility in flip-flops, you will have had my experience to testify that, yes, it is feasible.