with a small boat it will be a real drag. I've done it with my 32 footer up and down the northeastern coast. It will knock a knot off speed under best of circumstances. You will not be happy towing given your waterline.
I think you should investigate some kind of kayak that can be lashed down to your deck. Inflating and then deflating is just impracticable--at least I found it so, unless you spend a considerable amount of time in each port.