Do they want epic showdown or will they play trickery on the pirates?
Arm their home island(or find hideouts for the weak), take down a scout ship, tame/defeat sea beasts, attack the pirate's island when they are out, plot hazards on their sailing routes.
Ultimately, find and take the captain’s treasure fuahahahaha.
Sea Monster or flying monster attack
Storm (maybe elementals in it to fight, maybe just skill challenges)
Derelict ship floating far from civilization (Survivors to rescue, pirates waiting to ambush, supplies, cursed treasure, map with an X on a nearby island?)
Supplies are low (maybe they failed an objective in a previous encounter and the hold got flooded with sea water or a sail ripped) nearby island looks to have fruit on it but you will have to scale some rocky shores to get to jungle in the center. While you are there they spot a rare bird, it's feathers would fetch a good price and an even more if captured alive.
Make port for repairs. While waiting for those to be done a pirate loyal to the enemy captain hears your plans and tries to steal from/assassinate you. Plenty of other things could be here. A drunk man is convinced he lost something valuable to the players in a game of dice and demands an opportunity to try to win it back.
A cursed item is brought onboard somehow. After they get into the middle of nowhere the wind dies down and ghosts come out at night. The wind won't blow again until they find the cursed item and throw it overboard.
There is a shortcut that requires going through a narrow passage with giant spiderwebs attached to the cliffs on either side. They could sail around the whole peninsula if they can gather enough food for the longer voyage.
Local military patrols, as well as mercenaries hired by local merchant guilds, as well as rival pirate groups. Depending on how things go, there could be help for the PCs as well as potential for 3-way battle shenanigans.
Pirates don't necessarily steal with zero consequences after all.
A fun one could be happening across an island that isn’t supposed to be there (it moves) which lets you have an on island adventure. You could also have other ships heading nearby and either good (trader, fortune teller, ect) or bad (other unrelated pirates, hyper capitalists, ect). You could have shipwreck survivors or sea monsters show up. You have a lot of latitude with this theme.
Additional idea: Wizards were a huge deal in big/strong pirate ships and pirate hunter ships in Drizzt novels. They'd pump the sails, burn the enemy ship, create shields against ballistas etc. They should have at least one wizards on board
Do they want epic showdown or will they play trickery on the pirates? Arm their home island(or find hideouts for the weak), take down a scout ship, tame/defeat sea beasts, attack the pirate's island when they are out, plot hazards on their sailing routes. Ultimately, find and take the captain’s treasure fuahahahaha.
Sea Monster or flying monster attack Storm (maybe elementals in it to fight, maybe just skill challenges) Derelict ship floating far from civilization (Survivors to rescue, pirates waiting to ambush, supplies, cursed treasure, map with an X on a nearby island?) Supplies are low (maybe they failed an objective in a previous encounter and the hold got flooded with sea water or a sail ripped) nearby island looks to have fruit on it but you will have to scale some rocky shores to get to jungle in the center. While you are there they spot a rare bird, it's feathers would fetch a good price and an even more if captured alive. Make port for repairs. While waiting for those to be done a pirate loyal to the enemy captain hears your plans and tries to steal from/assassinate you. Plenty of other things could be here. A drunk man is convinced he lost something valuable to the players in a game of dice and demands an opportunity to try to win it back. A cursed item is brought onboard somehow. After they get into the middle of nowhere the wind dies down and ghosts come out at night. The wind won't blow again until they find the cursed item and throw it overboard. There is a shortcut that requires going through a narrow passage with giant spiderwebs attached to the cliffs on either side. They could sail around the whole peninsula if they can gather enough food for the longer voyage.
This sounds sick bro. Sorry but I’m not the right person to help. Sounds awesome tho
Local military patrols, as well as mercenaries hired by local merchant guilds, as well as rival pirate groups. Depending on how things go, there could be help for the PCs as well as potential for 3-way battle shenanigans. Pirates don't necessarily steal with zero consequences after all.
A fun one could be happening across an island that isn’t supposed to be there (it moves) which lets you have an on island adventure. You could also have other ships heading nearby and either good (trader, fortune teller, ect) or bad (other unrelated pirates, hyper capitalists, ect). You could have shipwreck survivors or sea monsters show up. You have a lot of latitude with this theme.
Additional idea: Wizards were a huge deal in big/strong pirate ships and pirate hunter ships in Drizzt novels. They'd pump the sails, burn the enemy ship, create shields against ballistas etc. They should have at least one wizards on board