Sorry, my mind was on Omena and not on Bowers Harbor. That could be good for you actually. Not sure how many transient slips they have but you can call and find out. Not many options unless in front of private property for anchoring. Also, if you are in Bower's Harbor, which is about 7 miles from TC. The Boathouse restaurant is also very good. A little more upscale than Knot, but very nice with a view of Bower's Harbor and a sunset if you are there at the right time.
From Bower's Harbor it is a run of about 10-12 NM to Suttons Bay or Omena. Based on what you want to do on Monday it would probably be best to finish at Bowers Harbor on Sunday afternoon and then you only have a short trip back to TC on Monday AM. I think that Elmwood and Clinch in TC are full for the weekend but maybe not Friday night. You can check them at www.michigan.gov/dnr
as they are both reservable harbors. The balance in the Bay are not reserveable but can usually handle a small boat on a wall or somewhere.
I also like to sail, but sometimes the wind says no and you do what you have to. The biggest myth is that you sail wherever you go. That may be true in a small lake where you can drift for the day, but in the Great Lakes the "iron jenny" gets used a lot. Case in point, I moved my boat from TC north to Northport today. Wind on the nose at 5 knots. I could have sailed but it would have taken me 10 hours or more. I pulled out of the marina, set the auto pilot, and was in NP in a little over 3 hours. In fact, I would still be out there and not sending this note. Now if it would have been blowing 10-15 I would have sailed, but 5..........not today.
Have a good weekend. Bring gas for the outboard and hope you don't need it.