I'm running Tyranny of Dragons campaign and we're currently in Chapter 4. The party is in Elturel at the moment and by the book, they should next head into Baldur's Gate and then take the caravan heading north to Waterdeep. And this is where my issue's at.
This portion contains a lot of traveling with only a few encounters. The book only states that travel from Greenest to Elturel and then from Elturel to Baldur's Gate happens without incident. Then, at Baldur's Gate, the party is supposed to wait around for the cultists to arrive which leaves again a couple of days of downtime. And when they finally arrive, it's a two month caravan journey to Waterdeep.
I can, of course, just speed things up and make the cultists arrive to Baldur's Gate faster and I've planned two social encounters for the party related to their backstories and previous campaign (we continued directly from Dragons of Stormwreck Isle with same characters). I'm not really that worried about the visit to Baldur's Gate in itself. But what I am worried about is that this constant travel and downtime will get boring and repetitive. And I still haven't figured out why don't the cultists just sail to Waterdeep? The only valid reason I can think of that it's more expensive than the caravan by land, but I don't think that's a good enough reason. We're talking about a cult trying to get a hoard of treasure somewhere safe quickly after all. I also want to include some realism into the story, so it feels more natural and logical.
Then, when the party eventually leaves Baldur's Gate with the caravan, the two months on the road needs some encounters. I don't find purely random fighting encounters – which don't advance the plot – to be that exciting, but the travel does need encounters nonetheless. The book offers a few good ones, which I'm going to take and I've also added two of my own encounters. But still, with the milestone level up system, they should have to work a bit for their level up when they reach Waterdeep and currently the journey lacks that work. They're only at Elturel, so there's plenty of time to come up with these encounters.
It's a big caravan and there needs to be reason for the party to be making decisions. It doesn't make sense that the party would dictate the actions of the whole caravan. I'm just struggling to find the proper encounters that would fit into this scope. Am I just too picky and thinking this too heavily?
How have others done this portion? Any suggestions and ideas for encounters for the travel to Waterdeep?
Honestly I just said "you travel from Baldur's Gate to Waterdeep and it takes two months" and didn't worry about it. Travel tends to be boring, random encounters lack purpose, so why bother with it?
I have a fun suggestion that worked out pretty well for one of the most chaotic D&D groups ever. I ran Tyranny of Dragons backwards for them where they side with Tiamat and the Cult of the Dragon instead of against them. It was very for me as well cause I got to make a premade campaign way more original. In fact, I am even compiling a guide for how to run it backwards that you are meant to use with the book to make it easier which I will post once it's done. I would also recommend starting your players at level 5 or 7 because lower levels are usually boring for both the players and DM because it is easier to accidentally kill the players and combat can take forever. I'm now realizing you were asking for a more specific thing and already started the campaign but you could still take this into account. Trust me, it's really fun and provides more of an excuse for players to be Warlocks or evil Paladins in this specific campaign which can be really fun. Serry for writing an entire paragraph BTW, I just like helping other DMs
Rollback Post to RevisionRollBack
ALL HAIL TIAMAT
I have 15 game systems and 60+ video games.
I also may or may not still be playing Skyrim for XBOX 360 (and PC) in 2026
Running an evil campaign could be fun, but my party is extremely lawful good, so it won't work in this particular situation.
We started level 1 with Stormwreck Isle as there were 3 first timers to D&D. I've already decided some homebrew content for them in Baldur's Gate related to their actions during Stormwreck Isle and their backstories. The things I've come up should keep the party busy and will also affect the ridiculously long caravan phase to make it more interesting.
Also, I figured that the reason the cult isn't going by ship is that they don't own any ships and unknown captains will want a log manifest when leaving port. The cult obviously doesn't want to officially state the amount of stolen valuables they're hauling north, so land route it is.
That's probably a big part of it: going by ship means getting official inspections by both Baldur's Gate and Waterdeep port authorities, but going by land is subject to less oversight.
Rollback Post to RevisionRollBack
Find your own truth, choose your enemies carefully, and never deal with a dragon.
"Canon" is what's factual to D&D lore. "Cannon" is what you're going to be shot with if you keep getting the word wrong.
We played Tyranny of Dragons a couple of years ago. I was not the DM for that campaign, I was a player. The moment you describe here is exactly the moment when our DM decided to start—not exactly homebrewing, but that was the point where he began to mix in a lot of ideas from other campaigns and things he had come up with himself.
I think the broad story beats of Tyranny of Dragons are actually quite cool. But you can really feel that it was one of the first adventures of 5E. There are parts of it that I really like, and they also show that not everything was as polished as it could have been yet.
So, to your question: you know your party—what do you think would make sense for them? In our case, our DM decided that we were going to Hell. He basically ran an Avernus adventure right in the middle of it, and it was a lot of fun. That would be my suggestion.
Two encounters I've decided is that the captain that took them to Stormwreck Isle was actually a pirate captain disguised as a legitimate merchant sailor. They'll meet him in Baldur's Gate by chance and he offers the party a deal. I'm hoping the party accepts the deal, but I also want them to feel a bit grudging as they now know he is actually a pirate. Accepting the deal would benefit them in the future, especially after Hoard of the Dragon Queen is over.
The second encounter is that they'll spend a night next to (or close to) a dead forest. During the night, Twig Blights and Vine Blights attack and steal some of the caravan's horses and start taking them towards a forgotten ruined structure. The ruin is a home to a Juvenile Shadow Dragon and contains a portal into the Shadowfell. I've also homebrewed a monster native to Shadowfell that has corrupted a dragon wyrmling to become a shadow dragon. Once the dragon is dead, the corrupting monster tries to corrupt one of the players or escape back into the Shadowfell when that fails. What I'm hoping is that they kill the dragon, close the portal, loot the dragon hoard, and get back to the caravan. But who knows, maybe they'll venture into the Shadowfell...
And that's about it. That's everything I've planned for them during the trip (there's the one or two ready random encounters that I'll drop at some point). My party has stated that they've actually enjoyed my creations more than the actual official story, so I'm optimistic about this as well. This is my first time DMing, so I'm afraid to sidetrack too heavily into a full homebrew sub-campaign inside the Shadowfell for example, which is why I asked for ideas and tips.
Maybe I'm just too much of a perfectionist and want the story as a whole to make sense. Maybe I just need to relax a bit and trust my party to enjoy the story.
I'm currently running Tyranny for my players and the caravan section was... interesting to say the least. I had 2 of my regular players need to drop out at that time (they were sent on "side quests") and needed to stretch it out for a month of weekly sessions.
I took a handful of the suggested encounters in the book and planned the 60-day trip scattering them in, with camp-based rest days every week (which it says in the book). Among that, I scattered in my own little encounters and it seemed to strike a good balance between camp-based RP (where my players could sneak into the Cult's wagons for information, interact with others in the camp, buy supplies etc.) and some combat every so often.
The only downside to this was that a lot of it felt repetitive and drawn out when I could have simply said to them that the trip passed without much incident and given them the chance to make some arbitrary dice rolls to see how much they found out.
Still, the players seemed to enjoy Life on the Road by not knowing what was going to happen (the doppelganger encounter was particularly good as they travelled with the camp, replaced some people and then attacked my party when they were resting in Daggerford, culminating in a weeks long campaign of having them second-guess what was going on). I think there's a lot of opportunity to flex your DM muscles a bit with it.
That's actually a wonderful idea. I hadn't thought of spying missions during camp time. But I think that instead of having separate camp encounters, I'll just fast forward it as a couple of charisma checks that they will do over the course of x days of conversing, prying, persuading, etc. After a few successes they'll eventually overhear a cultist slip out some essential piece of information.
Outside this I think I'll just run the few encounters and quickly narrating through the whole journey. Repetitiveness and boredom is what I'm afraid will happen on the travel and I want to avoid that if possible.
I've created one encounter for my party which should be interesting, but yet again, I need some help of tying it together.
Long story short they accepted the deal from the pirate captain I mentioned earlier. The deal involves killing an orc slaver leader who-is-not-quite-happy-the-party-killed-his-brother. The "problem" for the party currently is that they have no idea where that orc is or how to find him. Not really that big of an issue, it's only a side quest and there will be opportunities to meet him somewhere along the way.
BUT, they'll meet an old half-orc ranger on their way to Waterdeep, who has sworn to kill this same orc slaver. He's heard through animals that the party is trying to get to Naerytar – another thing they have no idea where it is. This ranger will offer them another deal: he will guide the party to Naerytar if the party is willing to do one task for him in Waterdeep. This task is to go talk to one person, who just happens to be a devil (the ranger may or may not know this, he's just not really fond of cities in general and avoids them if possible). The ranger has learned that this person knows where the orc leader is and wants this information. The devil is capable of casting alter self or shapeshifting into a human (is there a ready stat block for this kind of devil or should I just homebrew?).
I've never roleplayed devils, so what happens when the party meets the devil is a bit foggy. The devil should know the party's intent, and it also knows that Zariel wants Tiamat out of Avernus. The orc leader has made some sort of contract with the devil, like delivering souls for the devil in exchange for longevity or something similar. Why would a devil want to break out of this contract and have the orc slaver killed? What could he want from the party that makes it value them more than the slaver? Also, this is relatively early on in the whole campaign, so I might not want the devil to reveal the cult's overall goal just yet.
By definition, the devil should always be on top of things pulling the strings, so they should be in charge of the terms. And the party should really have to consider whether or not to make a deal with a devil as it will probably come to bite them in the future. After all, making the deal with the devil is not mandatory, it's just a way to find this orc immediately (but the party doesn't know this).
Rollback Post to RevisionRollBack
To post a comment, please login or register a new account.
I'm running Tyranny of Dragons campaign and we're currently in Chapter 4. The party is in Elturel at the moment and by the book, they should next head into Baldur's Gate and then take the caravan heading north to Waterdeep. And this is where my issue's at.
This portion contains a lot of traveling with only a few encounters. The book only states that travel from Greenest to Elturel and then from Elturel to Baldur's Gate happens without incident. Then, at Baldur's Gate, the party is supposed to wait around for the cultists to arrive which leaves again a couple of days of downtime. And when they finally arrive, it's a two month caravan journey to Waterdeep.
I can, of course, just speed things up and make the cultists arrive to Baldur's Gate faster and I've planned two social encounters for the party related to their backstories and previous campaign (we continued directly from Dragons of Stormwreck Isle with same characters). I'm not really that worried about the visit to Baldur's Gate in itself. But what I am worried about is that this constant travel and downtime will get boring and repetitive. And I still haven't figured out why don't the cultists just sail to Waterdeep? The only valid reason I can think of that it's more expensive than the caravan by land, but I don't think that's a good enough reason. We're talking about a cult trying to get a hoard of treasure somewhere safe quickly after all. I also want to include some realism into the story, so it feels more natural and logical.
Then, when the party eventually leaves Baldur's Gate with the caravan, the two months on the road needs some encounters. I don't find purely random fighting encounters – which don't advance the plot – to be that exciting, but the travel does need encounters nonetheless. The book offers a few good ones, which I'm going to take and I've also added two of my own encounters. But still, with the milestone level up system, they should have to work a bit for their level up when they reach Waterdeep and currently the journey lacks that work. They're only at Elturel, so there's plenty of time to come up with these encounters.
It's a big caravan and there needs to be reason for the party to be making decisions. It doesn't make sense that the party would dictate the actions of the whole caravan. I'm just struggling to find the proper encounters that would fit into this scope. Am I just too picky and thinking this too heavily?
How have others done this portion? Any suggestions and ideas for encounters for the travel to Waterdeep?
Honestly I just said "you travel from Baldur's Gate to Waterdeep and it takes two months" and didn't worry about it. Travel tends to be boring, random encounters lack purpose, so why bother with it?
I have a fun suggestion that worked out pretty well for one of the most chaotic D&D groups ever. I ran Tyranny of Dragons backwards for them where they side with
Tiamat and the Cult of the Dragon instead of against them. It was very for me as well cause I got to make a premade campaign way more original. In fact, I am even compiling a guide for how to run it backwards that you are meant to use with the book to make it easier which I will post once it's done. I would also recommend starting your players at level 5 or 7 because lower levels are usually boring for both the players and DM because it is easier to accidentally kill the players and combat can take forever. I'm now realizing you were asking for a more specific thing and already started the campaign but you could still take this into account. Trust me, it's really fun and provides more of an excuse for players to be Warlocks or evil Paladins in this specific campaign which can be really fun. Serry for writing an entire paragraph BTW, I just like helping other DMsALL HAIL TIAMAT
I have 15 game systems and 60+ video games.
I also may or may not still be playing Skyrim for XBOX 360 (and PC) in 2026
Also, please visit My WordPress Blog
Running an evil campaign could be fun, but my party is extremely lawful good, so it won't work in this particular situation.
We started level 1 with Stormwreck Isle as there were 3 first timers to D&D. I've already decided some homebrew content for them in Baldur's Gate related to their actions during Stormwreck Isle and their backstories. The things I've come up should keep the party busy and will also affect the ridiculously long caravan phase to make it more interesting.
Also, I figured that the reason the cult isn't going by ship is that they don't own any ships and unknown captains will want a log manifest when leaving port. The cult obviously doesn't want to officially state the amount of stolen valuables they're hauling north, so land route it is.
That's probably a big part of it: going by ship means getting official inspections by both Baldur's Gate and Waterdeep port authorities, but going by land is subject to less oversight.
Find your own truth, choose your enemies carefully, and never deal with a dragon.
"Canon" is what's factual to D&D lore. "Cannon" is what you're going to be shot with if you keep getting the word wrong.
We played Tyranny of Dragons a couple of years ago. I was not the DM for that campaign, I was a player. The moment you describe here is exactly the moment when our DM decided to start—not exactly homebrewing, but that was the point where he began to mix in a lot of ideas from other campaigns and things he had come up with himself.
I think the broad story beats of Tyranny of Dragons are actually quite cool. But you can really feel that it was one of the first adventures of 5E. There are parts of it that I really like, and they also show that not everything was as polished as it could have been yet.
So, to your question: you know your party—what do you think would make sense for them? In our case, our DM decided that we were going to Hell. He basically ran an Avernus adventure right in the middle of it, and it was a lot of fun. That would be my suggestion.
Two encounters I've decided is that the captain that took them to Stormwreck Isle was actually a pirate captain disguised as a legitimate merchant sailor. They'll meet him in Baldur's Gate by chance and he offers the party a deal. I'm hoping the party accepts the deal, but I also want them to feel a bit grudging as they now know he is actually a pirate. Accepting the deal would benefit them in the future, especially after Hoard of the Dragon Queen is over.
The second encounter is that they'll spend a night next to (or close to) a dead forest. During the night, Twig Blights and Vine Blights attack and steal some of the caravan's horses and start taking them towards a forgotten ruined structure. The ruin is a home to a Juvenile Shadow Dragon and contains a portal into the Shadowfell. I've also homebrewed a monster native to Shadowfell that has corrupted a dragon wyrmling to become a shadow dragon. Once the dragon is dead, the corrupting monster tries to corrupt one of the players or escape back into the Shadowfell when that fails. What I'm hoping is that they kill the dragon, close the portal, loot the dragon hoard, and get back to the caravan. But who knows, maybe they'll venture into the Shadowfell...
And that's about it. That's everything I've planned for them during the trip (there's the one or two ready random encounters that I'll drop at some point). My party has stated that they've actually enjoyed my creations more than the actual official story, so I'm optimistic about this as well. This is my first time DMing, so I'm afraid to sidetrack too heavily into a full homebrew sub-campaign inside the Shadowfell for example, which is why I asked for ideas and tips.
Maybe I'm just too much of a perfectionist and want the story as a whole to make sense. Maybe I just need to relax a bit and trust my party to enjoy the story.
I'm currently running Tyranny for my players and the caravan section was... interesting to say the least. I had 2 of my regular players need to drop out at that time (they were sent on "side quests") and needed to stretch it out for a month of weekly sessions.
I took a handful of the suggested encounters in the book and planned the 60-day trip scattering them in, with camp-based rest days every week (which it says in the book). Among that, I scattered in my own little encounters and it seemed to strike a good balance between camp-based RP (where my players could sneak into the Cult's wagons for information, interact with others in the camp, buy supplies etc.) and some combat every so often.
The only downside to this was that a lot of it felt repetitive and drawn out when I could have simply said to them that the trip passed without much incident and given them the chance to make some arbitrary dice rolls to see how much they found out.
Still, the players seemed to enjoy Life on the Road by not knowing what was going to happen (the doppelganger encounter was particularly good as they travelled with the camp, replaced some people and then attacked my party when they were resting in Daggerford, culminating in a weeks long campaign of having them second-guess what was going on). I think there's a lot of opportunity to flex your DM muscles a bit with it.
That's actually a wonderful idea. I hadn't thought of spying missions during camp time. But I think that instead of having separate camp encounters, I'll just fast forward it as a couple of charisma checks that they will do over the course of x days of conversing, prying, persuading, etc. After a few successes they'll eventually overhear a cultist slip out some essential piece of information.
Outside this I think I'll just run the few encounters and quickly narrating through the whole journey. Repetitiveness and boredom is what I'm afraid will happen on the travel and I want to avoid that if possible.
I've created one encounter for my party which should be interesting, but yet again, I need some help of tying it together.
Long story short they accepted the deal from the pirate captain I mentioned earlier. The deal involves killing an orc slaver leader who-is-not-quite-happy-the-party-killed-his-brother. The "problem" for the party currently is that they have no idea where that orc is or how to find him. Not really that big of an issue, it's only a side quest and there will be opportunities to meet him somewhere along the way.
BUT, they'll meet an old half-orc ranger on their way to Waterdeep, who has sworn to kill this same orc slaver. He's heard through animals that the party is trying to get to Naerytar – another thing they have no idea where it is. This ranger will offer them another deal: he will guide the party to Naerytar if the party is willing to do one task for him in Waterdeep. This task is to go talk to one person, who just happens to be a devil (the ranger may or may not know this, he's just not really fond of cities in general and avoids them if possible). The ranger has learned that this person knows where the orc leader is and wants this information. The devil is capable of casting alter self or shapeshifting into a human (is there a ready stat block for this kind of devil or should I just homebrew?).
I've never roleplayed devils, so what happens when the party meets the devil is a bit foggy. The devil should know the party's intent, and it also knows that Zariel wants Tiamat out of Avernus. The orc leader has made some sort of contract with the devil, like delivering souls for the devil in exchange for longevity or something similar. Why would a devil want to break out of this contract and have the orc slaver killed? What could he want from the party that makes it value them more than the slaver? Also, this is relatively early on in the whole campaign, so I might not want the devil to reveal the cult's overall goal just yet.
By definition, the devil should always be on top of things pulling the strings, so they should be in charge of the terms. And the party should really have to consider whether or not to make a deal with a devil as it will probably come to bite them in the future. After all, making the deal with the devil is not mandatory, it's just a way to find this orc immediately (but the party doesn't know this).