D&D 5E Help me to help my DM learn to water (a sequel/spiritual successor to my other thread)

Lanliss

Explorer
Oh Mighty [MENTION=6801286]Imaculata[/MENTION] I summon thee to request aid.

One of my players decided to be cool and try to DM. I wound up with a Privateer Swashbuckler/Warlock of Davy Jones, and kicked off an off-the-cuff Pirate campaign. We got by with some basic "make a survival roll" but I was wondering if there was a better way to handle navigating in New waters?

I am sure I will be able to think of more questions, but that is all for now. Thanks in advance.
 

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