Windrose gives you two ways to finish a naval fight: batter the enemy hull until it disables, then board across with grappling hooks, or keep firing from range and sink the vessel outright. The better choice depends almost entirely on which ship you are facing and how many enemies are still shooting at you.

How boarding works in Windrose
You cannot start a boarding action at full health on a moving ship. First, you have to damage the enemy vessel with cannon fire until it enters a disabled state. Your crew then throws grappling hooks and pulls the two ships together, creating a narrow bridge you cross on foot.
Before you try this, equip Boarding Gear at the Wharf. The fighting space is tight, dodging is limited, and the enemy crew attacks in close quarters. A musket works well for ranged kills while your AI crew absorbs melee damage. If your ship gets destroyed while you are still on the enemy deck, you can recall it at a Wharf afterward, and you can recall your ship during the boarding phase as long as no other player is aboard it.
What boarding rewards versus sinking
The core reward gap is simple. Sinking a ship gives you its standard drops. Boarding a ship adds a bonus payout on top of what you would have gotten by sinking it. The size of that bonus depends on the ship type and level.
| Ship type | Icon | Boarding bonus | Worth boarding? |
|---|---|---|---|
| Regular ship (level 2-8) | None | ~5-50 piastres | Usually no |
| Regular ship (level 8-15) | None | Around 100-150 piastres | Situational |
| Hauler / Transport / Freighter | Treasure chest | 40-250 piastres early, 500-1000+ at level 15 | Yes |
| Gunboat | None | Minimal | No, sink it |
Cargo ships marked with the chest icon also drop resource bundles like coffee, salt, gunpowder, and provisions when boarded, which is useful when you are stockpiling for a Brig or other ship upgrades.

When to sink instead
Sinking is the correct default in three situations. First, if the target is a gunboat or another plain warship with no chest icon, the bonus is too small to justify the time spent on the boarding minigame. Second, if you are fighting multiple ships at once, staying mobile and continuing to fire is safer than standing still on an enemy deck while other vessels shred your hull. Third, if your health is low, a quick clear from range avoids a melee fight you might not survive.
A practical rule in fleet engagements: sink everything except the cargo ship, then board the cargo ship last when the threats are gone.
What you lose if boarding goes wrong
Dying during a boarding action drops your inventory at your death location. You will need to return to recover it, either by sailing the dinghy (enemy ships cannot hit it) or by recalling your ship to your position. Losing the fight does not let you steal the enemy vessel, so there is no fleet-building payoff, only the loot bonus on successful boards.

How to tell a boarding worked
A successful boarding ends with the enemy crew cleared and a loot prompt showing the bonus piastres and any resources the ship was carrying. If you only see the standard sink rewards, the ship was not flagged as a cargo vessel, and the extra payout was small by design. That is the mechanic working correctly, not a bug.
Treat the chest icon as the single decision point. See the icon, board it. No icon, sink it and move on.