People use this idiom to imply that people who are quiet and don't try to attract attention are often more interesting than people who do try to get attention.
If you swim against the tide, you try to do something that is very difficult because there is a lot of opposition to you.
('Go against the tide' is an alternative form.)
If you're in uncharted waters, you are in a situation that is unfamiliar to you, that you have no experience of and don't know what might happen.
('Unchartered waters' is an incorrect form that is a common mistake.)