All of this depends on the wind.
Shouldn't be a problem if you take the outside route. The inside route is for small power boats.
Limiting depth on the small craft route is 6 ft. at datum. We are currently at chart datum and predicted to be between 8" - 24" above datum late June / early July. I've been from top to bottom of the small craft route with a 5 ft. draft and have seen sail boats bigger than mine along the way.
The distance is roughly 105nm depending on routing. If you can figure that you'll average a very conservative 4knots with prevailing south westerlies,
Prevailing winds are West or North west
then it should be roughly a 26 hour sail. This is based on a very direct offshore routing, west of Giant's Tomb, west side of the Watchers, east side of North and Long Island, east of Papoose Island. Great water the whole way AS LONG AS you stay east of North and Long islands. Be advised, you could be in for some serious swells coming off of Lake Huron if we get any sort of sustained (3 days) high (15knots+) winds from the west.
You'll never get swells from Lake Huron coming into Georgian Bay. Tobermory to Manitoulin are too close together to let swells have any major influence on the Bay. Any large waves you see on Georgian Bay are from the size of the bay itself.... and they will build
This would be outside the normal pattern though.
As a 2 week trip, it's more than doable. I would allow for 3 days of passage each way which would give a week with your friends.