TheSword
Warhammer Fantasy Imperial Plenipotentiary
I think there’s your answer. They got lucky and took a stationary/slow ship, through a novel set of tactics to take them by surprise.Good points on the movement. A ship under sail should outpace them.
In our scenario, the pirate ship was looting a merchant ship, spotted our PC's pirate ship, detached, fired some aggressive shots with ballista/catapult (the PC ship has a ballista but no ammo). The PCs faked fleeing (when in reality the PCs cast water breathing and leaped overboard). The pirate ship, once the ship was out of sight, returned to finish the looting. The PCs swam underwater, climbed aboard before the ship got to looting (the warlock used misty step to bypass an Athletics check to climb). Once on board, they focused-fired area attacks (not a lot of room to maneuver on a ship) to isolate the Captain and kill him (to demoralize the crew).
There is a roleplay aspect here. This guy was a wannabe pirate, but if they had attacked someone considered a true member of the Pirate Kingdom, they'd be marked for death. I'm hoping that will be a deterrent. They got lucky, this time.
So the enemy ship's advantage of movement was negated, though the PCs are certain to try and commandeer a better ship. I don't want to "thwart" well-laid plans by the PCs, but it seems to kill the entire notion of ship-to-ship classic combat. Given this world has some high-level Pirate Lords, what keeps them all from doing the same, whether it be flying, dimension door, etc.? That's my conundrum: what makes traditional sailing (speed) and weaponry (e.g. the new-age cannons that are popping up) relevant if magic can simply override it? What counter has the world come up with (such as glyphed hulls or special materials)?
Just make sure the next combat is moving under sail, to reset the expectations. They have to work the ship next time to close the distance, though I don’t think a ship boarding by the PCs is necessarily bad. The Pathfinder Pirate campaign Skull and Shackles openly discussed PCs boarding as the main method of the PCs taking a ship. Though they very quickly move away from the ship boarding being the main challenge. To other things.
The other reason for the PCs to use the ship more in combat is for the crew to really struggle without the PCs to command them. It’s an extension of don’t split the party. If bad stuff can happen to their ship if they leave it in combat, then they are less likely to travel far from it. They probably think they are protecting the crew by having the combat take place away from it. However if the ship is a pirate or military vessel relatively evenly matched then they should be wanting to take out the PCs ship, which is now bereft a captain, chief gunner, ships wizard etc.
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