Here's a photo of the Sailfish's predecessor, an early 1970's Sea Snark, on the same trailer:
I was actually able to tow the Snark down to the bay with the mast up. I was not foolish enough to try it with the sail raised, though.
But I was foolish enough to take the Snark out on the bay on a day that had some pretty good wind and some pretty good waves. Here's a couple photos taken on our return from its final voyage:
You can get
a pretty good canoe dolly that gets a boat off the ground high enough that you can hook the other end of it to the rack on your bike. I use that one for my canoe: