Tick anything you already have, in any order. Quests unlock once this is done.
Clubs own the boats and most have a training fleet. Crewing for someone is free, teaches you more than reading, and is how a lot of sailors start.
Find a sailing club near you2 things left above. Quests are real things you go and do, so they only make sense once you have what you need.
First one waiting: Sail a dinghy across the wind and back on your own