Sailors use the wind to travel for sport and adventure. We're brave, self-reliant, quick with knots, and super observant of the natural conditions - our life depends on it.
There are 3 "newb" one which are basically these that would allow you to get the skill without sailing! These challenges are mainly about knots (before the Knotter skill existed) or about some other sailing related things such as the wind or flags and so I won't talk a lot about them since they should be pretty easy to complete!
My favorite challenges so far would be definitely "Go Sailing" as well as "Create A Rigging Tutorial" because I have completed them and I had a lot of fun! I should probably start with the Rigging Tutorial since it will helps you to understand the basic of sailing as well as the different parts of the boats, trust me, there's a lot of parts!
Before hitting the sea, you should also try to complete the "Practice Man Overboard and Capsize Drills" challenge because practicing these things in a safe place will help you if something goes wrong! I used to be quite afraid of sailing, especially to capsize drill and I would be so stressed when I was on a sailboat! I am now a lot more relax when I'm sailing but it took me quite a while and so the best tip I could give you is to sail, sail, sail and sail again! The best way to come over your fear is to go sailing in a safe environment and become habituated. Also, having a small boat that is easier to understand and to un-capsize can helps a lot!
Finally, there's 4 "pro" challenges which are mainly about being more professional which means, joining a club or racing in a regatta!