In the Wind Waker HD, buying the sail from Zunarii requires freeing Tingle, and so takes a decent amount of time to obtain. Is it possible to skip it?
As the story progresses, KoRL has new lines of dialogue that are triggered automatically when Link gets close to him. In theory, the first instance of such a text occurs once the sail is obtained during the first trip to Windfall. However, by performing Outset Escape, it is possible to trigger some events out of order, including some events that make KoRL have a new text. If Link doesn't have the sail and goes near KoRL while he has a text cued up from these events, KoRL will ask Link the following ad vitam aeternam:
"Did you get a sail? There is no time to lose! You must find one, quickly!"
This results in a softlock.
Since beating FF1 to make KoRL appear is required to avoid a crash in Hyrule 2, skipping the sail can be more tricky than it sounds, eventhough sailing is not technically required to beat this game.
The first way to skip the sail is to simply not trigger any events that give KoRL a text line. Here are some of these events:
The first three dungeons can be skipped thanks to the Early Master Sword sequence break. Skipping bombs entails performing Puppet Ganon Skip using a frame perfect bow shot to reach the final fight with Ganondorf (TAS-only):
To avoid the softlock despite obtaining bombs, bombs must be obtained AFTER beating the Forsaken Fortress 1. If they are obtained before that, the softlock will happen right after the FF1 cutscene. Here are the two most complicated aspects about skipping the sail:
After beating FF1, the savewarp location is set to the beach on Windfall Island. One way of avoiding the softlock is to void-out somewhere in the ocean in order to spawn in KoRL, triggering the last savewarp flag. Now, if you savewarp to leave the pirate ship after getting bombs, you will spawn back on the docks on Windfall instead of on the shore, which is far enough away from KoRL to avoid the softlock. Spawning on the shore instead would have triggered the softlock.
If you did obtain the Spoils Bag, leaving the pirate ship after getting bombs makes Link spawn at Windfall where the pirate ship is supposed to be during endless night, which avoids the softlock. If you don't obtain the Spoils Bag, leaving the pirate ship will put you on the "leaving Outset" map, and since savewarping would trigger the softlock there are no ways out.
Note: To obtain the Spoils Bag after performing Outset Escape, you need to enter the pirate ship during the day while not having triggered the gossip stone text in FF1, since that text makes the pirate ship interior have rope game 2 instead of rope game 1.
It is possible to simply roll or walk away from KoRL. If you are not fast enough, you will softlock.
The swift sail doesn't avoid the softlock, only the normal sail from Zunarii does. If you do obtain the swift sail before the sail, you won't be able to get the normal sail anymore because Zunarii stops to sell it.