Re: Can I make this trip as a novice
The best guy to ask is the guy staring at you when you shave -- if you've got his vote, then go for it. Just make sure both you and him are in full agreement, and that you both do your homework (to include picking a good weather window.)
We covered part of your route when we were heading for Holland, MI from the Chesapeake.
One of the great things about Michigan is that they have state park marinas, and they usually are no more than a half day's journey apart. If things get a bit nasty, you can duck into one to wait for better weather. When we were coming up from Port Huron (in late August) we took a maintenance/laundry day in Port Sanilac, then ducked into Harbor Beach for a couple of days when the weather turned against us.
Even if your time/distance calculations for the run from Port Huron down to Lake St Claire tell you you can make it in a day, plan a couple of bail-out option marinas as well.
Sounds like it'll be a good shake-down cruise.
Oh -- get the tow insurance. It's worth it, even if it's only for the peace of mind.
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'85 BYB Vagabond 39