A small rowing craft can be a real joy. I spent endless hours every summer as a youngster rowing around a large lake in an uncle's small runabout, and used an eight-foot dingy pram as a tender when we were into sailing. Both were stable, seaworthy boats for their size that were a lot of fun to use. A decent little rowboat could suit you and your son's needs just fine.
A smaller canoe - something in the 14' range - is another possibility. If you find one with reasonable beam, a double-blade kayak paddle can make paddling solo a lot easier. I've also seen canoes equipped with modifications that let them be rowed. I'm not a big fan of canoes on salt water, but then the ocean around here can get pretty rough pretty quick, and the water's always cold. A decked kayak is, i.m.h.o, no place for anyone who can't escape a capsize and re-enter unassisted - i.e., children, beloved dogs, aged aunts, etc.
Great to see you and your son looking to the water for a way to grow together - our two girls grew up camping and canoeing with us, and those memories are what binds us all together. Enjoy, and take care out there.
2-3 Canoe/Kayak Trailer
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