Forgive my jumping into this thread a little late, but I think I can offer some useful experience.
When I bought my TF about a dozen years ago, it couldn't have been easier: Seller was in Boston and I almost immediately found (via craigslist rideshares) a girl who was driving from there to Portland via Montana, where she had family. We met up in Great Falls, which is an easy day trip from here, I paid her a grand, and hauled it home, doing the customs clearance en route.
After that, when I bought the SC19 from Long Island NY last summer, I thought getting it here would be easy. Boy, was I wrong. Someone suggested uship, and the quotes I got were up around $5K - more than twice the value of the boat - so that was a non-starter. I screwed around with craigslist for a couple of
months with a series of people over different possibilities. Best would have been to get it to Montana (as previous), but I didn't mind driving further to an adjacent state for the handoff, and since I was facing an Oct.1 deadline (when the marina where it was being stored was scheduled to close for the season) I was willing to just get it as far as my pal's place in Madison WI (where I thought I'd be able to pick it up in the spring - good thing that didn't happen, thanks to the border closure) or even his coworker's place in NJ -
anything to get it off Long Island. At one point I had a guy ready to do the NY-NJ run - for $500, which was just stupid, and I kept hearing about what a nightmare that part of the drive would be. One prospect fell through after the other, and October passed, and on Nov.1 I just said "screw this, I'm driving", and hit the road. The trip took nine days, cost me about a grand, I got to stay with my bud in Madison twice, and hung for an evening and had a
terrific supper at a hardcore kosher deli on Long Island with Bobby, the boat's PO. And for the record, getting from Long Island, across Manhattan, and to New Jersey wasn't any different than towing a cat around LA freeways, which I did a bunch of a long time ago - no big deal.
So my original experience, and that of the previous poster, constitute pure luck. Nothing better than getting a bargain from someone who's otherwise deadheading, that's for sure, but if you're off the beaten path you could be SOL. Start looking early.
As for the (Canadian) border crossing, do it yourself. I'd never dream of trusting someone to do the customs clearance for me. For the craziest possible trailering-stuff-over-the-border story, you might like this (bit of a long read, but you're stuck at home and have time on your hands, right?):
https://nitpickingbastard…-of-the-sea-doo-trailer/Edited by jonathan162 on Jan 13, 2021 - 02:28 PM.
--
Southern Alberta and all over the damn place.
*
1981 SuperCat 20 "Roberts' Rockets"
1983 SuperCat 19
TriFoiler #23 "Unfair Advantage"
Mystere 17
Unicorn A-Class (probably made by Trowbridge) that I couldn't resist rescuing at auction.
H18 & Zygal (classic) Tornado - stolen and destroyed - very unpleasant story.
Invitation and Mistral and Sunflower and windsurfers w/ Harken hydrofoils and god knows what else...
--