Just to follow up this thread, I've done considerable work on the directsail code and I think most of the problems discussed here should be eliminated.
Island transitions on the normal map are smoother except for a couple: anything involving Isla Mona and going from Curacao to Aruba. I put code in place so that Isla Mona won't appear using directsail on the normal map, but will on the open sea map, and you can always get there on the world map. Additional code is in place but commented so that people can add conditions where Isla Mona has to appear. Curacao to Aruba ain't right, but it's reasonable: once when sailing a fast ship I was close enough to moor immediately upon transition. If you're not going 18 knots, you might find it works well enough. Actually, that's true for any transition on the normal map.
There were several instances of your ship not appearing in quite the right location on the map, at least before directsail had a chance to run, but I think I've got all those fixed. I've done a lot of sailing on both the normal map and the open sea map and I haven't ended up somewhere I didn't expect lately, and my ship is always where I expect it to be on the map.
There were a couple of bugs that would cause you to teleport to open sea on transition, and I hope I've got those covered as well.
There is some wonkiness when returning from the world map near an island, but I don't think it's anything I can fix.
Sailing on the open sea map shouldn't have been a problem before, and it works as intended now... any problems from before just weren't visible. I think the problems that people encountered with it were due to a problem in the loader code, and that should be fixed as well now.
Hook