Dry Sailor, I sail a Hobie 17, and love the boat, but I love the 16 too, and suspect that a 16 would be better for sailing two up. I would say that your weight, and prospective crew weight are of vital concern in this decision. Where will you be sailing? The 17's tramp is so low to the water that it can be a source of drag in chop with too much weight on the boat. As a solo boat I love it, and if your combined weight isn't above 270, it can be great with crew as well. I have a jib for an 18 on mine, and it definately makes a big difference in helping with extra weight, as well as sailing downwind.