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. To see what skipping bombs entails, see the Bombs Skip page.
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. The most troublesome part about avoiding the softlock when getting bombs happens right as you're obtaining the bombs in the pirate ship.
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.
The most convenient way to spawn in KoRL without the sail from Windfall is to superswim to Dragon Roost Island, enter and leave Beedle's ship to make KoRL appear on DRI. Then by voiding-out by superswimming out of the map, you will be put on the boat on DRI. Almost anywhere on DRI, if you go into the water and savewarp, you will be put on the DRI shore (casually, this was to avoid you from entering KoRL before obtaining Din's Pearl). This skips having to cruise or do a manual superswim to the shore, which you would have had to do anywhere else.
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.
If you got the bombs, KoRL will be able to softlock you. However, in Hyrule 2, Link spawn just far enough from KoRL to not softlock. As such, it is simply possible to simply roll or walk away from KoRL.
You can still softlock in Hyrule if you go closer to KoRL.