in the wind. The answer is blowin' in the wind."
The Wilderness was designed for a paddler and a load of gear, so you can expect that with only a paddler, it'll sit light on the water and blow around a little.
One thing you could do is to make up an emergency bag containing what you would need if, while out on a day trip, you were blown to shore and stranded. A minimalist tent, pad, sleeping bag, some long-storage food, etc. Allow yourself maybe 50 pounds. Seal it up in a dry bag, and whenever you're out on a day trip, have it tied in your boat just in front of you. (Mind the trim.) Another supplementary source of ballast is a camel water bag on the bottom of the boat.
Taking these things on all day trips, you will be safer and the boat will be within its load design range.
2-3 Canoe/Kayak Trailer
Kayak Deck Gear Bags
4-place Boat Trailer