I liked the game from the first day I played (Feb 2016, 1574 hours), but I'd have to say that my first wow moment was when I joined a clan and we started our campaign against the (Aussie) Brits around Bonacca. It was a battle that lasted a couple of months and we were almost always outnumbered. Those fights taught us how to sail and fight as a group and we even won our share of battles. I can still remember the first time I saw a Santisima explode in a battle in Bensalem Harbor. We laughed the rest of the night- if I remember correctly it was one of Merrill Stubings gang which made it even better.
Since I was little I've been captivated by the sight of ships under sail. I keep playing the game because it is a beautiful game to play and I've met dozens of friends on TS over the last year plus.
I've played POTBS, Sid Meiers 'rats, Port Royale II, and I even go all the way back to the Ancient Art of War at Sea on a monochrome monitor. This game tops them all.
Here is one of my favorite screen shots from back in the day. I'm running a flag in my Merc at 103 knots...lol.