Midland is our home port and we cruise
that area extensively. Crossing east from Tobermory should be easier as prevailing winds are in your favour. Wingfield Basin is a good stop to wait for weather
but you probably already know that.
If you aim for Pointe-Au-Baril, enter through the main channel then make your way south to some nice anchorages on Shawanaga Island. If you have a decent dink, go through the "hole in the wall" to Ojibway island, with a side trip to Hemlock channel.
From there to Parry Sound and south, there are too many possibilities to list here. Use Active Captain
and the Ports book and slowly make your way south through the Small Craft channel.
If the weather
is very calm and settled, you can jump ~10mn offshore
to the Western Islands. Go early as there is room for only one or two boats, anchored and stern tied to iron stakes on the Crescent island. This place is unbelievable.