It's not like any other posts have gotten slightly off topic before.
Phreak, Midland Bay, Penetang Bay and the area out to Christian Island, Hope and Beckwith are fairly protected waters and you can spend a good days sailing in those areas. It's not until you get beyond Christian that you are out in the open "Bay". Some days it can be nasty, some days it can be calm. I know lots of smaller boats that cross the Bay, but only under ideal conditions as it can kick up a substantial storm that you would not want to be out in a larger boat let alone a smaller boat. But it all depends on etc. etc. and is a bigger discussion than this thread.
You can also get into the inland channel without going into the main part of the bay and cruise for days in fairly protected waters.
Bottom line.... there's lots of smaller <30' in this area.