I'm in a winter planning mode trying to figure out how to best prepare for a possible voyage across Lake Michigan next summer.
I'm reading charts, looking at weather history (wind speed/direction for seasonal trends, not guarantees), talking with sailors who have done (albeit in races on larger boats) what I want to do, and learning Garmin's Homeport application and my new Garmin GPSMap 78sc.
It seems to me that my first effort on big water should be short, so that first trip will be a bit more than 10 miles along the Lake Michigan shore from Muskegon Lake to White Lake. (I'm still figuring out Homeport so the detail of this image is not very good.) The magenta line represents a track from Muskegon Lake northward to White Lake. The plan is to sail to White Lake, raft up with another boat for the night and return to Muskegon the next day. I'd like to do this trip as early in May as possible, and do longer day-sails as conditions allow throughout May.
Another trip I am looking forward to is crossing Lake Huron's Saginaw Bay. I'm thinking from Caseville, MI to Tawas City, MI in early June. Tawas City hosts a festival in June with a "traditional boat" gathering the first weekend of the month. The trip across Saginaw Bay is about 20 miles, give or take depending on wind speed and direction.
The Saginaw Bay trip would involve the sail across, two nights (maybe three) in Tawas City (probably in the State marina), and sail back to Caseville (weather permitting).
Discussing a Lake Michigan crossing with more experienced sailors has been encouraging. None of them said, "Don't do it." Several suggested other trips - not necessarily using Sheboygan, WI as the destination - that will be worth looking into for later in the summer. (Sheboygan is my destination as that is where a Welsford Boats get-together is tentatively planned for sometime in July.)
So, I continue to study, plan and add to Gardens' kit, fully aware that planning on paper in the cold, dark months of winter is not the same as getting out there and sailing!