Carl:
I kept my boat on Winnebago this summer, so did not get any Bay of Green Bay sailing done. I do know, though, that the "cut" you refer to between the Bay and Lake Michigan now has three bridges to contend with. Here's a URL to the NOAA chart for the area:
http://www.charts.noaa.gov/OnLineViewer/14919.shtmlI'm not sure I would take the 19 onto Lake Michigan alone, if at all. It can get rough. Still, here's my take on the situation you're asking about:
Coming from the Lake Michigan side, the first bridge is the Hwy 42 bridge. It's plenty tall enough (42 feet) to clear the 19's mast. That will get you into the city of Sturgeon Bay and a number of marinas where you can tie up and take a break. The second bridge was just opened recently and the chart does not list a clearance, but the third bridge, the Michigan Street Bridge, is shown at 14 vertical feet, so I expect the new one is not much higher. You would need to have them opened to pass into the Bay of Green Bay. Fortunately, there is a lot of recreational traffic through there, so you can get in line and scoot through (under power is the surest way).
Once through the bridges and onto the Bay, you would go left (south) to the City of Green Bay or right (north) to the scenic areas of Door County.
Good luck!
Jim