I just put the big ice chest down on the deck where its easy to get to when you're thirsty... Oh thats right I have a Stiletto 27, you can walk to the ice chest to get a drink!

On the other hand, on my previous H20 and TheMightyHobie18, I would either strap the soft cooler to the tramp as noted above or bungie it to the boom about a third back from the mast. Its off the tramp so it dosen't get in the lines, its far enough forward so you don't hit it while crossing. If you do hit it while crossing, its softer than the boom so its not bad.

Clayton