Time alone
While you do not have to walk alone. I believe that better ideas come up when you walk alone. Many intellectuals and great minds spent much time alone. People may call them schizoids. Experts in personality disorders argue that they are rare personalities rather than disorders. These can change in the course of your life. Spending time alone does not have to make you schizoid. Many successful people did just that. Einstein, Jung, Nietzsche, Schopenhauer, etc. It is not like they never saw people, but much of their time was spent alone. It can be one of the steps towards success.
Walking is relaxing, simple and a great activity. But I wouldn't recommend rushing it, or going for big distances immediately. Short distances are fine. I would recommend walking in nature. Slow speeds are ok. Walking doesn't have to be competitive. Walking in the cities has more noise, is distracting and less relaxing.
Death march in barefoot shoes
I am participated in a death march, which means walking a hundred kilometers in one day. Doing hundred kilometers likely isn't healthy, but it is an achievement which requires passion and strength. I have experienced muscle pain, but I got no blisters. Reflex spray helped to reduce the muscle pain. But I wouldn't have made it without other supportive people.
Different people within Dover Fueling Solutions participated. Here is a picture with one of my colleages. My phone camera isn't fantastic though. 
Recovery after death march was quick. All I had is some muscle pain. Although the death march was difficult. I will not do it again, but might do similar activities. I did notice a few other people with barefoot shoes. Hundred kilometers is even harder than it sounds; it can feel never-ending.
Route issues
The route had issues. We often had to wait very long, and at one point I almost fainted because I couldn't breath well in a crowded area. When I sat down in the middle of the crowd, I could get air; if I didn't do that I may have stopped around the thirty-kilometer mark. Many people around me did faint.
During the last fifteen kilometers it felt like blisters on my two big toes wanted to develop, but they never did. I did change socks around that time, maybe they weren't pulled up well. Resting didn’t help anymore as the pain persisted, but pushing through that isn’t easy. Reflex spray came in handy, as it often suppressed or stopped muscle pain.
Results
My overall speed wasn't that fast for good reasons. We had a lot of slow-downs in the beginning. It wasn't possible to walk faster. Towards the end we took no rests anymore. After that many kilometers you slow down, and you want to arrive on time. During my trainings I walked slightly faster than five kilometers per hour.
It is time to buy new shoes after death march. The ones I used have lasted long. They were in a similar state when I started the death march. They still function. The sole on one side is slightly coming off, probably because I do not always cleanly remove my shoes. On the inside there is some damage from the heel, due to walking on hard ground, which requires a bit of impact. I do not tend to heel strike much.
I used insoles during the death march and in my final training for it to reduce the discomfort from walking on hard ground. Although I am not sure of it made much of a difference.
You can find info about barefoot shoes on my barefoot shoes page.