Back when I was young I spent the summers there with my granddad. He had a 16' planked skiff and a 10 hp outboard. We would leave the boat basin and go SW down the bay for day fishing. In the afternoons the winds would pick up and there would be 2' waves with a reasonable trough such that the 16 was plenty of length since the wind and wave sources were to our rear (astern). Had it been the reverse it would not have been all that nice. The bays were shallow which was good if you got swamped but bad as it affected the waves.
Additionally, most afternoons contained a squall which is a spontaneously occurring, very short, intense, thunder storm with high winds, lightening and stinging, high volume, rain. If caught out in the bay in one of these, which we were on more than one occasion, the boat required bailing to prevent it from sinking...we had no flotation other than the fact that the boat was wood planked.....not that much.
I think it would be in your best interest to reconsider your aspirations.
HTH,
Mark