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