We sold our Road King a while back, so my answer is based on what fits in DH's Honda ST something or other saddlebag. I tried a Tamrac Messenger bag, Adventure Messenger 4, and it fit really nicely in the saddlebag and held quite a bit of gear. It also had pretty good padding. But I didn't like the interior of the bag since every time I took something out of the bag, it would get caught on the strips of velcro that run around the inside of all the compartments. So, I returned that bag. But I liked it because the size was perfect for the saddlebag. Right now, I use my Crumpler $5mil bag, but it is a bit of a squeeze on the width and your gear would not fit in that bag.