Great advice MBounds!!
We have done this trip for years.. The organizer does a pretty good job.. We have all or passports and info all lined up and sorted in a binder.. Even going so far as calling ahead... We generally don't have problems.
The couple times which we have On the way into Canada they asked about Potatoes... Which we had..
(why they bought them in the USA knowing full well I dunno.. )
but we pull an enclosed trailer with the gear... and the potatoes were in the front of it... So crossing into Canada we ended up unloading most of our crap to throw them out.. It was weird though.. Here were are doing all of this on the Canada side.. With no supervision nor inspection...
Then this year coming back into the states on the "father/son" trip... The occupants of each vehicle didn't match the way the passports were organized.. So in full view of the Border the knotheads decided to pull a Chinese fire drill to straighten it out.... Brilliant!!!! They didn't just zip through that time like we usually do... You don't screw around at the US border... Ya just don't..
I just didn't know what Canada might want on the sailboat. I sure don't want to burden everyone with another huge piece of gear... and then end up being "that guy" at the border also..
Oh... the trip website..http://buddiesforlife.org/
Good times for sure!