INPUT question????

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Very broad question. If they have been single handing already and boat is properly equipped then they should know if they are comfortable. I have not done it but I would suggest the primary "new" challenge vs normal cruising for many might be the many locks.
Not a requirement but a bow and stern thruster with remote would be very helpful.

Suggest they join GLCA and directly do the research. For this site a more detailed question about concerns as well as info on the boat and their experience will get better responses.
 
Doing the Loop is such a huge topic that I'd recommend watching lots of YouTube videos posted by those who are doing it, or recently done it. Years ago when we bought our first bigger boat and started thinking about the Loop someday, YouTube blogs (or "vlogs") by Loopers weren't nearly as common as they are now, but now there are piles of them out there. In fact watching videos and reading a lot eventually made us decide to skip the bottom half, concluding that we could spend the rest of our lives just from Duluth and "over the top" to say Chesapeake Bay, and never get to the bottom half. I've always thought though that even if I could single-hand (although locks sure don't look easy to solo), if my wife and maybe our boys aren't with me, that would be a lonely trip. I'm no Moitessier or Joshua Slocum.
 
Doing it solo I would want bow and stern thrusters with a wireless remote. Too easy for the boat to blow off the docks and lock walls while you are moving from helm to side deck to handle lines. With the remote and thrusters you can bring it back to the dock or wall pretty easily.
 
Check out our very own member Jeff F , and his extensive online page Boating Adventures

I think he's one of the most widely and frequently traveled folks around.
 
What sort of input is your friend looking for?

I've looped 3 times solo, and there are always a few folks doing it in various types of boat. Joining AGLCA is probably a good start.
 
If I were doing it I would want good access from the helm to the deck where you handle lines. Some boats have horrible access.
 
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