I hunted the sound once in my 23' Tolman with a 140 hp. Long story short, a friend came up from the lowe 48 for three weeks, we had a three day weather window and made it out to Disk Island. First night it rained 6". When that storm finally blew through, we made it back, which included driving every wave on the way back to Culross and taking some green water over the bow.
IMHO, it isn't prudent to plan taking anything under a 28 footer with twin 200's or better yet twin 250's through Well's Passage in the fall. You might get a whether window, then again you might not. Same on the return.
Three people adults with hunting gear on a 21' skiff with a 50 horse is a bad plan for hunting PWS. It's a marginal boat for three people to fish on a blue bird day in the sound.
