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