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As a guy that kayak fishes pretty much all year round, yes, it is possible to do it safely. There are lots of knuckleheads out on the water at all times of year, and in all kinds of kayaks and boats alike.
Personally, I've got a full drysuit, VHF radio, life jacket, and a PLB attached to my life jacket. We had some nice weather back in October and November and I saw guys in jeans and hoodies giving the rest of us a bad name. I'm wearing my drysuit generally mid-September thru late May. But I'll even wear it occasionally during the warmer months if the night time temps are going to be a little low, or on the rare occasion I'm out by myself.
Point being, yes it is possible to do it safely. I feel far more safe in my kayak with all my gear than I would in some of the little tin boats I see on the Sound. As far as I'm concerned, as long as the weather isn't uncomfortably cold, I'll fish if I have the chance (and the reason). Holdover winter stripers don't do it for me anymore, I'd honestly rather catch calicos, perch, and catfish as long as the spots aren't frozen over.
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