The first time I went on crutches was 1997; I had broken my ankle in the middle of a wrestling match the day before leaving on a cruise for spring break (still won BTW). That was a very difficult place to be with a broken leg and on crutches, and I was ill-prepared. This was back with the old wooden ones that were fairly flimsy, and extremely uncomfortable. Being that I was young and stupid (as opposed to a little older and stupid now), I once walked over a mile and a half on them. That sucked.
The second time I went on crutches was in 2003 for just a few weeks when I had a partial tear in my MCL. I don't recall any long walks, but remember crutches being a real pain. The third time, in 2011, I made some discoveries in how to really maximize your self-sufficiency, safety, comfort, and sanity while being on these damn things! Now that I'm on my fourth go-round with crutches, I'm an old pro, and it's never been easier for me to get around with them.
Here's my list of the top 5 things you need to have when you're on crutches, from an expert: