Re: Purchasing a Sailboat from the US?
I'm not a pro on Canadian customs, but my understanding is this is done all the time. Particularly crossing the Great Lakes. Assuming you are a Canadian citizen, I believe you just show up with your new boat and immediately check in with your Customs, which you would do anyway, tell them you are importing the boat you are on and pay your taxes. I'm told those taxes are breathtaking. We have two Canadian neighbors at our marina that will never bring their boats home, for that reason.
Be sure you know you have clear title to the boat and have proof of what you paid for it. In the US, title (ownership document) may be issued by the State or it could be documented with the USCG. Don't be confused by registration, which is entirely different and only signifies ones permission to keep a boat within a State's waters for an extended period.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.