Tip: That writing top right is quite hard to read, I recommend a different font and to have each of the names of crews the same color, and then give each one a Colorued pins to mark them on the map as a “key”, like you are pinning onto the map.

There are absolutely hundreds of “push pin icon packs” out there.

Another option could be to use a different medieval weapon to represent each crew.

Like I know you can get medieval push pins

Fonts

As for fonts, check out the “scripts” section of dafont.com

They even have a selection of free pirate fonts.