Ok so my players are often at sea when they need to travel from place to place. That's fine, the water can be dangerous, but they take longer routes to avoid said danger but still be faster than on land. They do this because they're still relatively low level (All level 4 with 4 players) and can't fight most water monsters that stay in the water to attack. Problem is I'm set to only a few options for encounters. I can do a Sahagian attack but 1: You can't do that more than once unless it's a story plot which it isn't and 2: Whenever something has to scale a ship to attack players it becomes a grand version of Whack-A-Mole which gets boring for players. So, what about pirates than? Well than there will be some kind of ship battle. And in this case the player's ship is not made for combat at all with only one basic cannon for defense. A pirate's ship would easily decimate them as long as it used its long-ranged attacks. So that's my dilemma, I don't know what threat I can throw at them that will be a challenge but also survivable. Hopefully there's a better DM than I who can help me with this problem.
1. You don't need to have a ship battle. Filler content isn't always necessary.
2. You can have a sahuagin attack, and they sneak up during night so they are already on the ship when combat starts
3. Pirates would not use a cannon to take down a ship, as they usually want to keep the ship intact and take the ship itself, as well as its crew and cargo.
4. Harpies are always a good ship enemy (or other flying creatures)
5. The crew could attack them for a variety of reasons
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Any sufficiently widespread magic is indistinguishable from technology.
The second funniest thing to make a D&D party do is explain morality
Concerning pirates the above is correct, they want the cargo so they will try to board and minimize damage, as they might even want the ship itself for treasure.
Do both you and the party want an encounter or are you following a plot and feel you must have a water encounter?
Is the party able to breath in water to attack a sea creature? If so use a sea monster, otherwise stay away from them.
If you want Pirates, have the pirates, follow outside of cannon range, about 3 hours before sunset, the pirates disappear and stop following. About 3 hours after sunset when it is dark, the Pirate ship emerges out of the gloom, and approaches the ship from the 10 o'clock position. Announce the pirates ate about 15 minutes away.
The ship captain damns a light that is lit on the steerage deck (tells the party how the pirates found the ship)
Roll initiative before the pirates show up to determine where the party goes and what weapons they have. Give the players a short amount of time, so that they don't have all the time to grab what they need.
Have the pirates board and do combat. The pirates are properly prepared, the party is only hastily prepared.
You can repeat this again and again, have the pirates sometimes find the ship sometimes not, have it at different times of the night. By changing the routine, you use the threat of an encounter to play on the players psyche.
Of course, you can also just skip. If you can't really think of anything interesting, and your players are trying to go somewhere else anyway, just say the sailing was uneventful and skip to them arriving at their destination.
As others have said journeys can just be uneventful. I've almost completely stopped doing random encounters during journeys because they do little to add to a story, they're just happening because a random roll told me that it was time for 4 bandits to attack, so unless I've got a planned encounter that will add to the campaign in a meaningful way like conveying a breakdown in law and order or the spread of monsters I just don't bother. My players leave one place, get flavour text about the trip, and arrive at their destination
I'd highly discourage you from doing random encounters. They are inevitably going to get boring unless you have purchased a book with really neat and creative monster designs. Default Monster Manual monsters are not going to cut it to be an interesting encounter.
Instead, I'd suggest thinking about them in terms of "side-quests" something with some kind of narrative to it which the players can choose to pursue or ignore, and which might tie in to the overall plot. For example, for a nautical journey:
1) Stranded survivors of a wreck. These can be used as a ticking-clock type encounter e.g. with sharks circling the survivors and the party have to rescue them / scare / kill the sharks before the survivors get eaten. Or as a social/survival encounter if the player's ship doesn't have enough supplies to feed the rescue-ees. They also can foreshadow a plot-related threat based on what it was that destroyed their ship.
2) A half-sunken wreck on a reef. Make it a rich/luxurious ship to incentivize the players to go explore it, and have some creepy / scary stuff for them to discover within the wreck if they do that explains why such a fancy ship ended up wrecked - e.g. evidence of a disease that sickened/killed the crew, or strange arcane runes that were placed as sabotage by a rival they can discover in a passenger's journal, or a mutiny due to the ship getting lost and running out of rations and the survivors becoming mad cannibals to survive, etc...
3) A bermuda-triangle-like strange whirlpool / storm magically created as protection for a secretive underwater civilization that will become relevant later in the story.
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Ok so my players are often at sea when they need to travel from place to place. That's fine, the water can be dangerous, but they take longer routes to avoid said danger but still be faster than on land. They do this because they're still relatively low level (All level 4 with 4 players) and can't fight most water monsters that stay in the water to attack. Problem is I'm set to only a few options for encounters. I can do a Sahagian attack but 1: You can't do that more than once unless it's a story plot which it isn't and 2: Whenever something has to scale a ship to attack players it becomes a grand version of Whack-A-Mole which gets boring for players. So, what about pirates than? Well than there will be some kind of ship battle. And in this case the player's ship is not made for combat at all with only one basic cannon for defense. A pirate's ship would easily decimate them as long as it used its long-ranged attacks. So that's my dilemma, I don't know what threat I can throw at them that will be a challenge but also survivable. Hopefully there's a better DM than I who can help me with this problem.
Homebrew Stuff:
The Umbravore
Some possible options:
1. You don't need to have a ship battle. Filler content isn't always necessary.
2. You can have a sahuagin attack, and they sneak up during night so they are already on the ship when combat starts
3. Pirates would not use a cannon to take down a ship, as they usually want to keep the ship intact and take the ship itself, as well as its crew and cargo.
4. Harpies are always a good ship enemy (or other flying creatures)
5. The crew could attack them for a variety of reasons
Any sufficiently widespread magic is indistinguishable from technology.
The second funniest thing to make a D&D party do is explain morality
Try your hand at the Ultimate Skill Build Challenge!
I probably nitpick and scrutinize too much
Pirates wouldn't want to sink the ship, they'd want to disable it. They can't steal the cargo if the ship is on the bottom of the sea.
Concerning pirates the above is correct, they want the cargo so they will try to board and minimize damage, as they might even want the ship itself for treasure.
Do both you and the party want an encounter or are you following a plot and feel you must have a water encounter?
Is the party able to breath in water to attack a sea creature? If so use a sea monster, otherwise stay away from them.
If you want Pirates, have the pirates, follow outside of cannon range, about 3 hours before sunset, the pirates disappear and stop following. About 3 hours after sunset when it is dark, the Pirate ship emerges out of the gloom, and approaches the ship from the 10 o'clock position. Announce the pirates ate about 15 minutes away.
The ship captain damns a light that is lit on the steerage deck (tells the party how the pirates found the ship)
Roll initiative before the pirates show up to determine where the party goes and what weapons they have. Give the players a short amount of time, so that they don't have all the time to grab what they need.
Have the pirates board and do combat. The pirates are properly prepared, the party is only hastily prepared.
You can repeat this again and again, have the pirates sometimes find the ship sometimes not, have it at different times of the night. By changing the routine, you use the threat of an encounter to play on the players psyche.
Of course, you can also just skip. If you can't really think of anything interesting, and your players are trying to go somewhere else anyway, just say the sailing was uneventful and skip to them arriving at their destination.
As others have said journeys can just be uneventful. I've almost completely stopped doing random encounters during journeys because they do little to add to a story, they're just happening because a random roll told me that it was time for 4 bandits to attack, so unless I've got a planned encounter that will add to the campaign in a meaningful way like conveying a breakdown in law and order or the spread of monsters I just don't bother. My players leave one place, get flavour text about the trip, and arrive at their destination
I'd highly discourage you from doing random encounters. They are inevitably going to get boring unless you have purchased a book with really neat and creative monster designs. Default Monster Manual monsters are not going to cut it to be an interesting encounter.
Instead, I'd suggest thinking about them in terms of "side-quests" something with some kind of narrative to it which the players can choose to pursue or ignore, and which might tie in to the overall plot. For example, for a nautical journey:
1) Stranded survivors of a wreck. These can be used as a ticking-clock type encounter e.g. with sharks circling the survivors and the party have to rescue them / scare / kill the sharks before the survivors get eaten. Or as a social/survival encounter if the player's ship doesn't have enough supplies to feed the rescue-ees. They also can foreshadow a plot-related threat based on what it was that destroyed their ship.
2) A half-sunken wreck on a reef. Make it a rich/luxurious ship to incentivize the players to go explore it, and have some creepy / scary stuff for them to discover within the wreck if they do that explains why such a fancy ship ended up wrecked - e.g. evidence of a disease that sickened/killed the crew, or strange arcane runes that were placed as sabotage by a rival they can discover in a passenger's journal, or a mutiny due to the ship getting lost and running out of rations and the survivors becoming mad cannibals to survive, etc...
3) A bermuda-triangle-like strange whirlpool / storm magically created as protection for a secretive underwater civilization that will become relevant later in the story.