It'll still be a present. But hold off until he's had a little demo/class time to get a basic sense of what he wants, then pull out a checkbook. It is quite likely that you will find a good match in this process, and used is great because no one has to worry about who got the first scratch in the boat. You can help carry it without worrying about repercussions the first time you go thru a tight space.
You are talking full out sea kayaks for that area, so a bad choice is likely to be a pretty expensive one.
4-place Boat Trailer
YakCatcher Rod Holder
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