You can trip in the north woods with a kayak. It's just not very practical.
Decked boats have great advantages in conditions in which wind and large waves are likely to occur, like the open ocean. Wind and waves can kick up on the larger lakes up in the Boundary Waters, but they are not the predominate characteristic of that type of tripping.
Kayaks are more awkward to portage than canoes, and much more awkward to load and unload repeatedly when multiple portages per day are required. Relatively few people will select a kayak over a canoe for that type of tripping in protected inland waterways.
If you really want to do solo tripping in the Boundary Waters with a kayak, carve yourself a portage pad out of minicell foam that slips into the side of your cockpit and fits the contour of your cockpit coaming. Shape it to fit your shoulder and it will allow you to portage the boat on one shoulder while carrying your paddle in the other and a pack on your pack.
Canoe / Kayak Anchors
URCHIN Portable Anchor
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