Hi, Marty,
Smallest boat I ever took through the gut was a 26' sloop. Took longer than I planned to get there from Shelter Isl. so I missed slack water... tried to fight an outgoing (southbound) tide anyway... under sail (bad motor) ... in light air. This was 15 years ago. I remember large formations in the water, which resembled 'standing waves' like in white water canoeing... except there was less foam, but *much* larger, smoother waves, with holes bigger than my sloop between 'em ... tacking and tacking, trying not to drift sideways into, literally into one of these monsters... eventually, unable to make any headway, we turned around, or maybe just eased off and slid backwards into calm water in Gardiners' Bay. 3 or 4 hrs later it was a different story.. calm and easy...
The previous weekend, we were up in port Judith, getting the motor allegedly repaired, we almost sailed out of that harbor with plans to shoot the gut... but didn't... weather just too rough. We heard later on the VHF that a cabin cruiser of some sort was fishing in the gut, and *pitchpoled* with fatalities.
So, check your tide tables. If I'd had your hobie, who knows, mighta shot upstream through the Gut much easier than my old tub. Might be fun!