Considering the amount of territory you want to cover in a sail boat, recommend that you leave south sound for another day. Too many factors will affect getting from one anchorage to the next. I suppose if you powered all the way from dawn to dusk it might work, but finding a nice anchorage where you can spend a day or more exploring the island brings more gratification, IMHO. Likewise, a slow sail to the next anchorage ten miles away makes for a better spirit than pushing a thirty or forty mile day under power, exhausted upon arrival.
We all have our preferences, but for us, sail time receives top priority. If it takes spending an hour or two bobbing until we reach an approaching wind line, that is time well spent. Powering is always a choice, but finding that obscure bit of illusive wind to pull us along breaths with satisfaction. But that is just us. Just say'n.