Jesse,8 footer, mount it on the gunwale...Shakespeare Galaxy...
I don't remember what Jesse's boat looks like but here is what I did on the Key West I had. Rail mount ratchet. I kept the antenna pointed straight down unless I was intending to use the radio. Pointed up I got 15 miles easy. Never in the way of anything.
If your leaning towards the shortie Shakespear I'd go for the Gam electronics SS-2 It has a stainless steel body so you don't have to paint the reviews of it are great. Here is just one such link: http://continuouswave.com/whaler/refere ... tenna.html
It received just fine with the antenna down but I would not transmit unless it was up. Higher gain does concentrate the radiation pattern