Is it possible? How quickly does, say, a rowing boat gets destroyed on the high seas? I've had one experience with it and that's when oceans were first implemented, I moved into the high sea area on a rowing boat for 1-2 seconds and the boat was instantly destroyed. I haven't tried it since so I don't know if that was a case of being unlucky and having that tick of damage come so soon or if that is literally the norm.
If that was just a case of being unlucky and you can sail out a fair bit before it getting destroyed, maybe it's possible to do something like having 2 throwaway alts in a rowboat, holding rowboats of their own, each with 2 dugouts in said rowboats, so in theory you can sail across, boat gets destroyed, jump into one of the 2 rowboats that drops, get the alts in, have one pick up the other rowboat and the other grabbing the dugout from the cargo as you continue sailing through.
....Is that too impractical? Particularly when you have to guess which area of ocean has the shortest distance to cross. Seems pretty impractical but like I said I don't know how quickly on average rowboats get destroyed. If they can last a few minutes each it might be possible.