That's unbelievably cool. If my dad were younger he'd love to do that with me I think, though not sure he's ever sailed, but he's been around fishing boats and whatnot his whole life.
I would think that's far more interesting of a way to travel than by long-distance car rides, which bore me to death often, and you're stuck in such a confined space for so long. Would be fun to have the sun and wind on your face, though i don't know how these larger sailboats work.
Does the coast guard ever give you much grief? Once you cross into American waters do they tend to leave you alone? And going into shore painless in terms of authorities bothering you?
Well for starters I bought my boat in the States so it already had American registration numbers on it. But no, once you cross the border and jump on the boat, nobody bothers you, including the Coast Guard. They're just around in case you get into trouble, which luckily i never really did. (somehow) Going ashore to tie up for a night and maybe get the laundry done and restore the land legs is no different than pulling off the interstate at a motel for the night.
My mom was not a boater, especially ones that tipped over a bit when the wind blows, but I did convince her to come for a visit in mid January one year. She was in Toronto and I was in Key Biscayne. Lets see, minus 25 vs plus 25? She had a good week.