u/Need2Sail and u/emilepetrone et al,
It's great that you are asking questions. There are no stupid questions, only dumb answers. Sometimes the truth is harsh. *grin*
For short distances it isn't too hard. You draw a straight line between A and B. Pay attention to the bits with land and shallow. Fish traps, crab pots, wrecks. Lay in a reasonable path to miss those things. Check the weather. Where is the wind expected to come from? Is your path achievable? Adjust accordingly. Don't follow in love with your plan. No plan survives contact with the enemy, and reality is your enemy. Oh - tides and currents may be a factor depending on where you are. We can talk about that separately.
You do need to know what you are looking at. A friend of mine has a book that has had good reviews. https://www.amazon.com/How-Read-Nautical-Chart-Understanding-ebook/dp/B007SMEBG2/ref=sr_1_1?crid=33EA8ZFF2CZPG&keywords=how+to+read+a+nautical+chart+nigel+calder&qid=1562953552&s=gateway&sprefix=nigel+calder+charts%2Caps%2C198&sr=8-1 Note that you can get NOAA chart #1 free on line. Nigel has tried to provide additional depth to the explanations of each bit. I think he was successful. $15 on Amazon in the US.
If you aren't in the US or otherwise in IALA region B you have to swap things around for red and green marks being reversed (red right returning to sea rather than red right returning to port *sigh*). Cardinal marks are rare in the US; in other parts of the world "western women wear bikinis." If anyone has a more politically correct mnemonic I will be grateful.