In their policies it says "No windsurfing equipment" in general terms, but I can't see why bunching a few sails together would be any different than a duffel bag or likewise how a few skinny masts would bother them. Anyone tried?

Also - Can you use the travelers exemption on duty on goods you ship back separately? (if I can't get air canada to take them for instance) I figured this information would be easy to find, but even finding the amount you are exempt for is hard enough.

you are permitted $750 from what I recall after being away for over a week, you pay duty on the difference. No you cannot go and pick it up later or use it on a package you receive. However you can mail it to yourself and call it a "warranty item" or "gift" with no value....
I think there is a length restriction with Air Canada so a 460 or a board exceeds it typically but shorter units do not. The maui guys will know...

Air Canada sucks on all levels I am sorry to say since it is our national airline, I will never fly with them again Those old farts at the backage and checkin counters are the worst pricks ever.
Last year I poured myself into a tiny TransAt seat just to avoid them and it was a much better experience despite feeling like a sardine Even flying with a bunch of pimple-faced 16 year olds at Westjet is more confidence inspiring.

North West takes Windsurfing gear to Maui and it only cost me $80.00 each way. You fly Horizon to Seatle and then direct to Maui.
West jet and Air Canada don't take the gear still!!!

They might not fly to Maui, but Singapore Air, never charged me a dime to take 3 sails, a 430 mast, and an alum boom, all the way to Perth Australia and back. Free booze from an exceptionally gracious flight crew as well.