Two suggestions that might help her out for longer rides:
1) change out the seat. The stock seat on the S40 isn’t great if you are riding more than 2-3 hours.
2) get a windshield. Getting the wind off her chest will probably make the ride much more enjoyable- whatever bike she is on.
As for a canoe… rent one when you get there.
In the end, trailer your bikes if you want to. Not all bikes are good for a long haul, and you should ride your bike the way you want to, when you want to. Some of us are weekend warriors, some of us ride full time, but the key, what we all have in common, is that we love riding.