Here is the full list of all 31 Windward achievements. It takes around 40-50 hours to unlock all of the achievements on Windows.
Establish a foothold in a region where your faction has no towns.
Successfully complete a commission to place a Guard Tower near a town.
Defeat an enemy by yourself without taking any damage.
Complete 50 commissions.
Repair your ship while obscured by fog.
Become a true pirate. Arrr!
Make a town grow in size.
Upgrade your ship.
Do your first trade run.
Defeat a Pirate Captain.
Achieve a skull kill rating.
Defeat 5 pirates.
Hire a follower.
Open a Sealed Letter.
Customize your ship's look.
Complete your first commission.
Complete two consignments at the same time.
Find and equip your first epic item.
Unlock all ships.
Defeat 100 ships.
Defeat two enemies back to back.
Completely drive out pirates from a level 9+ region.
Equip an item that will push any stat above 1000.
Drop Grogolov on top of 3 or more enemies.
Opt out of a PvP match by using a White Flag.
Capture a level 9 or higher region in a co-op match.
Sink a pirate captain in a level 39+ region.
Sink another player in PvP.
Drive out pirates from a level 39+ region.
Achieve the Admiral reputation standing with any faction.
Complete the Strange Diagram quest.