I actually tested this out. I found these baselines:
Say your destination is directly north of you, and it is precisely one screen away, 1000 of the units displayed on the map.
Here's the times it would take to complete this trip based on the wind direction assuming you are travelling straight north.
Wind is:
- North - 60 seconds
- Northwest/Northeast - 70 seconds
- West/East - 80 seconds
- Southwest/Southeast - 200 seconds
- South - Never
South direction is assuming you do not push forward on the control stick. If we assume that the units given on the map are meters, then you can translate these times into common ship speeds: 32.4 knots, 27.8 knots, 24.3 knots, and 9.3 knots. Which are actually are reasonably realistic for a boat that size. If the units are in yards, which I doubt, they'd still be roughly the same.
To get these times I used a timer and the Tingle Tuner map to see exactly when I crossed the section. I wasn't able to test this with the quick sail thing though because I couldn't do the trick, and watch the Tingle Tuner, and the timer at the same time. But if you can cross a section in less than 60 seconds while doing the trick then you know it works. If it's the same or more then you know it didn't work. So that should help.