Tick anything you already have, in any order. Quests unlock once this is done.
A lake or a slow river, not the sea, and not anywhere with a current. Hire before buying, because an inflatable is a real commitment of money and cupboard space.
Find paddleboard hire2 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: Paddle away from shore on your knees