I really like the extent you have gone to to make mechanics as clear as possible, that too in appropriate contexts. I also liked the idea with the movement mechanics, although it took me a while to 'drift' (like car 'drifting'; idk ship lingo) properly for better results.
A few things that come to mind are-
When displaying the instructions, give a little more time gap before showing a text after another. In the first level where it says the sail follows mouse, I missed the text that the corner arrow is pointing wind direction. I noticed this text only when I finished the game and started the second time. In all of the first run, I thought the water waves were moving in the wind direction xD
Wind direction could be displayed in a more immersive way. You could try experimenting with the cloud movement, water movement, or some other particle effect, etc. but it should be very clear at all times.
It feels a little counter intuitive to follow the arrow and head straight into land if the destination information is unclear. In the final level I noticed all the pirates grouped up. Then in the second playthrough, I realised that there were tiny sprites of pirates on all the islands. You should make it more obvious to the eye that the island is the target.
It's a very cool idea and the mechanics are fun. With further polish, it can be more enjoyable. If you make a post jam version, I hope you add more levels with diverse gameplay experience. Overall, nice work!