I pulled a boat from washington state a couple years ago, I t was a breeze. You need to have bills of sale for both the trailer and boat. I was able to get a permit for my trailer in seattle to haul it home also. At the border if you have all your paperwork you will pay pst and gst on the boat and pst on the trailer when you insure it(this is in bc but check your province). You also have to pay a fee for importing the trailer (forget what its called) and it covers the cost when you take your trailer to Canadian tire to get inspected that it meets canadian standards.