Welcome aboard!
That should be a great trip. In June 2021, we brought our O'Day 30 from Benton Harbor, MI, to Detroit. We left June 2.
Be ready for any temperature. It could be COLD, it could be hot & sweltering. On the northern lakes, be ready for
fog at any time of day. Warm moist air gets blown over the lake & makes
fog.
I can't speak to the WI side of the lake. The Michigan side has lots of picturesque little towns with nice, state harbors. All are worth a visit. Some have farmer's markets and or
music on Friday or Saturday. Avoid Leland. It's a very neat place to visit, but the harbor entrance is prone to silting. Beaver Island is a great place to stop.
Northern Lake Michigan is full of lighthouses. They mark
reefs, shallows, and other unfriendly things. Pay attention and have a plan.
Mackinac Island is worth a stop. Rent a bike & see the sights outside of town.
Harrisville, MI is REALLY trying to attract cruisers. The have
music in the park at the harbor on Friday nights.
The St Clair and Detroit rivers are fun. You will probably be motoring. There can be LOTS of traffic. In places, there are "middle grounds" in the middle of both rivers. It's possible to be in the middle of the river, with only 3 or 4' of
water depth. When in any doubt, follow the freighter channel.
Be prepared to
motor. We sailed about 5 hours TOTAL on our trip. Our average apparent
wind was almost always under 5 knts, but sometimes over 30.