extreme novice advice

[hlprmnky]

It’s not clear if you found the kayaks too hard to sit in comfortably or if paddling around was simply too tiring. If it’s the latter, and if you really do want to sail instead of get around the lake in a motor dinghy, I actually think you might consider a Hobie Mirage Tandem. It’s an 18ft tandem kayak with detachable amas and an unstayed mast with a roller-furling sail.

They are definitely on the “expensive toy” end of the spectrum of options suggested so far, but if you both can sit comfortably in a kayak it would be hard to beat having sail, paddle, and pedal options to move around, and that trailer you posted would carry one easily.

I don’t have any affiliation with Hobie or anything, my local chandlery in Benton Harbor, MI happens to have one of these sitting out front perpetually for sale (I can’t imagine they would be very much fun to use on Lake Michigan but there it sits, season after season). As I read your post, more and more I thought “huh, it actually sounds like that trimaran sail kayak thing they have at Wolf’s would be good for them.”

https://www.hobie.com/kayaks/mirage-tandem-island/

[Greatest Lakes]

Yeah. Wolf's has had that thing sitting around for several years now. It does seem like it would be interesting.
For smaller, comfortable trailer sailors, Com-pac makes some very easy boats, though a bit more money sometimes. Very easy, safe rigs. Though for peak comfort and ease of use, a console RIB might be the way to go, even if it is power, much of the new 4 strokes are very quiet and reliable. They are comfortable, easy to operate and quite safe.