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I've gone the other way.. it's pretty straightforward, esp if you buy a North American built boat (I didn't and had to pay duty on top of taxes). Be careful of 80s Beneteaus - only because many were built in France and as such subject to duties when imported. A pristine one might be worth the added costs in duty, but be sure.
Good time for it now, with our dollar dropping against the USD.
I haven't been up to Canada since a fly in fishing trip 8 years ago. I will never forget a comedian referred to Canada as an attic. Every once in awhile you go up there and are shocked by what you see (which is only beauty for Canada).
I would live there in a minute if I could (for 5 months in the summer that is)!
Lots of good Canadian-built plastic right across from you in central/eastern Ontario. Check kijiji.ca ... just make sure it's got the HIN or builder's plate visible, or you have appropriate documentation (Transport Canada registration form, if it's got, but many <10hp don't) so you don't get hassled on import.
Trailerables may command a little price premium over a Grampian or Tanzer 26, but $5k should put you in the game just fine.
Like Faster, I too have gone the other way. Was no big deal at all. Had to un-Document the boat in the USA, and then get it licensed up here. Had to pay Canadian taxes. Luckily our boat was North American-made so we avoided the 9.5% NAFTA import duty. Other than shelling out the cash, it was quick and pretty simple. I assume the reverse process is equally easy.
One thing you Americans have (once again) is the fact that our currency has gone back into the crapper. This means your dollar is worth almost $1.25 up here now. That's a 25% discount off the asking price for you folks, so it might be wise to cast your gaze north right now, just as it was for us when your economy tanked back in 2008 -- that's how I ended up with my current boat .
If the boat was built in the US, it doesn't matter where it is presently registered, you won't have to pay import tax.
Contact the appropriate Canadian agency to get it deregistered there, before you bring it back, to facilitate registration in the US. Your state may charge you fees to register it and some states charge sales or a use tax, like Fla.
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