Posted by: nycmhandy on Mar-17-13 11:55 PM (EST)
I paddle all the time with kayakers -- I in my fast solo canoe. I can usually go faster than most of them. There is one guy who is always faster than I am, but he is faster than all the other kayakers, too. Only once, going through Hell Gate against really strong winds, did kayakers have to turn back and make sure I was all right (I was fine, just "slightly delayed").
On the other hand, there are things I won't do. I prefer edges to crossings; I choose my crossings for minimum risk and minimum distance, when sometimes the more skilled kayakers will intentionally choose the longer, rougher crossing. Having decks and bulkheads and rigging can make up for a lot of missing skill; it's hard to outfit a non-whitewater canoe for an ocean-style crossing.
Overall, I would say that, for a wide range of moderate conditions, a solo canoeist can paddle with a kayaker, if both have experience in similar conditions and both are willing to put up with minor inconveniences related to the choice of craft. As conditions worsen, the canoeist's skills and judgement need to improve much faster than the kayaker's. And there comes a point where you just have to have a deck and bulkheads (in a sea canoe, possibly -- nothing magic about a kayak's seating position).
Finally, I wouldn't go on a risky trip with people I hadn't paddled with before, regardless of what kind of boat they liked. If rescues were at all likely, I would want to practice rescues with them. You would find out more by paddling with these people, gradually ramping up the risk and difficulty, than you will by armchair reasoning. If they are sensible and the risk is too much for them, they will bow out and save you the difficult decision.