Almost forgot, and someone else …
mentioned it below.
make sure you have a skirt.
Cheers,
JackL
Other considerations
I agree with all the safety comments others have made. I would also suggest water temperature may be a problem even for good swimmers in lake Michigan.
Another problem I see is the difference in the 2 boats you are talking about. Most people like to get in a boat, set up a paddling rhythm and continue. If you have a sea kayak (almost any) and your friend has a 9.5 rec boat, you will either have to keep stopping and starting up again (which is a pain) or the two of you aren’t going to paddle together. I have seen several “paddling couples” end their paddling days almost before they get started because their boats are too different and at least one (if not both) person gets upset with the other over speed or effort (or lack there of) when really the problem is with the difference in boats.
Most books suggest to plan 2 or 2.5 mph as a speed. I suggest your butts are going to be sore before you have made it around the island. When you start a few hours is all your butts can take.
Enjoy and have fun. Don’t let “the plan” get in the way of enjoyment.
Amen…
Paddlin’on or Swimmin’ on
Richard