I have no experience (yet) of sailing that area, however we plan to sail the Grand Traverse Bay and Manitou Islands this July. As members of the Great Lakes Sailing Club we are able to tap into a wealth of member information and recommendations. I highly recommend that you join if you plan on sailing the Great Lakes very often. The discounts you receive from marinas and businesses always more than pays for the annual dues.
In the Grand Traverse Bay area we plan to base ourselves at Sutton's Bay Marina and day-sail to Traverse City, Bowers Harbor, Elk Rapids, Old Mission, Northport, and Leeland. All of those small towns are highly recommended for dining, shopping, and exploring if you like that kind of thing. The area is well know for their cherry and blueberry crops as well as their local wineries and craft beers. They are big on festivals so check their websites if you would like to catch one.
The Manitou Islands are on our agenda for their excellent hiking and exploring. You can anchor off each of them then dinghy in for a day of exploring. They had been previously settled then abandoned so there is a lot of history to explore. If you plan to anchor overnight it is recommended that you anchor in the NE bay of South Manitou Island. More information on their websites.
As you sail from the Manitou Islands towards the Michigan shoreline and perhaps Leeland Marina you will be headed towards the Sleeping Bear Dunes National Park. It won the title of 'Good Morning America's Most Beautiful Place in America'. Its a long story but audience members voting online selected it above all others in America. Can't wait to see it!
I have way too much to share here. Let me know if you would like more information. Have fun!