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Nerdarchy > Dungeons & Dragons  > New DM Handbook: Pirate’s Cove (My Tutorial Quest)

New DM Handbook: Pirate’s Cove (My Tutorial Quest)

Tabletop RPG Combat Isn’t Always About Trading Blows
There is only one rule! Trials and triumphs of a full-time nerd in a part-time world

New DM HandbookA couple of months ago, I laid out an article about the usefulness of a tutorial quest for new players. I’ve since referenced it a number of times in other articles, but I haven’t talked about the results, which I promised to do after finishing the quest with my party. A promise that I haven’t yet kept until now, mostly because there have been other articles that were more pressing or more relevant, for the moment. Especially in the light of my article last week about starting your adventure, which included the mistakes I made, now is the perfect time to share the tutorial quest I made, how things went, what I would do differently, and the overall lessons I learned.

Pirate’s Cove

Pirates CoveThe quest itself is designed for four to five level 1 characters. Five is preferable for new players, but four is doable. The story dictates that the party is (individually or by group) recruited by the crew of a smuggling ship that was raided by pirates. Because part of what I’m doing with my games is including references to other media, including books, plays, movies, television, and video games from every corner of my knowledge base, which adds an extra element for my players to always look forward to, I chose to base it off the Serenity (a sailing ship for this quest) from the Firefly TV series, but there’s no reason to limit yourself. For those who would like to use them, here is the most basic rundown of how I D&D-ized each character:

Malcolm Reynolds: Dragonborn Battle Master Fighter, Rebel Soldier

Zoë Washburn: Tiefling Champion Fighter, Rebel Soldier

Hoban “Wash” Washburn: Half-Elf College of Valor Bard, Sailor

Jayne Cobb: Half-Orc Path of the Berserker Barbarian, Pirate

River Tam: Human (Variant, Keen Mind) Way of the Open Hand Monk, Urchin

Simon Tam: Human (Variant, Healer) Life Domain Cleric

Kaylee Frye: Stout Halfling Gunsmith Artificer, Sailor (I’m coincidentally working on a Tinkerer class that would suit her better.)

Shepherd Book: Human (Variant, Observant) Knowledge Domain Cleric, Acolyte

Inara Serra: Protector Aasimar College of Lore Bard, Guild Artisan

Admittedly, I changed a few things for this article, but what I originally had wasn’t a great match, so I’m making the call.

If you choose to go with a completely different crew, I would still highly suggest making them adventurer-level characters and to have as wide of a variety of classes as you think is reasonable. That way, if you feel the need to add one of them to the party to fill out some gaps (especially if you’re short players), you have them on hand. I had another character I created using a Sorcerer that I made with a healing class archetype, mostly so I could test it, but also because my party didn’t have a healer. It was a really good thing that I did, too.

River TamI would also have some dialogue options for the crew of your ship that’s going to help provide insight into the quest. As an example, in one of the encounters I set up two extra enemies hiding for the purposes of a second wave/surprise attack when the party is in a more opportune position to be ambushed. River, being a “reader,” had a premonition about there being “two more.” I put her in the crow’s nest, so my players had to seek her out if they realized she wasn’t immediately visible, which one of them happened to. Because he did, throughout the entire quest they were constantly on the lookout for two more enemies, although they didn’t know where they’d come from.

For the sake of easy reference for the rest of the quest, I’m going to give a quick breakdown of the enemies I used. For the sake of it being a tutorial quest and allowing my players to try to more easily grasp combat, I used only a few different types of enemies. Basically, I used bandits and re-skinned them as pirates:

• Pirate Sentry = Bandit

• Pirate = Bandit

• Pirate Sergeant = Bandit, modified to be a CR 1/4 (AC 14, HP 16)

• Pirate Thug = Thug

• Pirate Captain (Jack )= Bandit Captain

Raven’s Peak


Raven’s Peak is a port city. It’s where the party is recruited. I’m not going to include a map of the town because I’ve designed it to be quite malleable. Outside of the docks and the main roads that run north/south and east/west that quarter the city, the buildings and the roads that extend beyond them are severely haphazard. There is no central city planning, and businesses are allowed to build as they please, as long as they own the land, and construct roads to ensure there is no interruption to the flow of traffic. City maps are rare to come by, since they probably won’t be up-to-date for long enough to be worthwhile, so those not local will have to constantly ask where things are and where to get things.


The party is recruited and meet up at the ship (Serenity). The smuggling ship captain (Malcolm Reynolds) hires the party to help them recover medical supplies destined for a Halfling village but stolen by Pirate Captain Jack. If players are independently recruited, select crew members that would be most prone to recruit the player characters from locations where the player characters would most likely be at the beginning of the campaign.

What Happened

Each player was afforded the opportunity to role play their introduction, and I offered them a role-play element on the Serenity, which was only lightly touched on as most of them were itching to roll dice. A fully understandable desire, especially for new players, and compounded by the fact it took about 45 minutes to get through the introductions. In hindsight, I should’ve streamlined the introduction, even if I still stand by the structure.


• 2x Pirate Sentries (50 xp)

On the beach is a small haystack rock. Off to the east is an empty beach, immediately to the west is a campfire with the two pirate sentries. Further off to the west is a river flowing northward. The players are dropped off further to the east, moving toward the river as instructed by Malcolm, while the crew of the Serenity draws as much attention from the pirates as they can from the eastern side of the island. The players eventually come across the pirates. The players can see the flickering of the campfire and the smoke from behind the haystack rock, and they can hear the pirates messing around.

The Lesson

This first encounter’s sole function is to introduce combat in the safest space possible. It answers how you roll for attacks and damage, and provides an opportunity for the players to plan their attack before jumping in. Optimally this is a surprise round, unless (as my Wood Elf Rogue managed to do) one of them rolls a 1 in a stealth check. Of course, that’s assuming they consider trying to attempt a surprise attack, which may not always be obvious for new players or those who just plain prefer to jump in swords a-swinging.

What I Learned

It’s not a bad idea to have all of the pirates have some kind of information for the players to discover, as I quickly learned. The party chose to keep at least one of them alive to be able to interrogate. However, they spent the better part of about an hour interrogating the prisoner they managed to not kill, which was completely unnecessary. It’s best to provide them with detail on how to navigate the pirate’s island before you start, preferably at the start of the quest. It’s okay to let your new players know the quest is going to be strictly linear for this one time because this as much about learning how to play the game as it is actually playing it. The way it’s set up, they’ll be at level 3 right before the boss fight.

First Skirmish

• 2x Pirates (50 xp)

• Pirate Sergeant (50 xp)

The party follows the river north where they come across a patrol of pirates. The pirates are just patrolling for a general threat of attack that would be likely on an island controlled by pirates, whether against authorities or other criminals. It’s a lightly wooded area, so there’s plenty of visibility. The players and the pirates meet at a small dirt road where they can plainly see each other coming.


The Lesson

This is a minor step up from the previous encounter, teaching both the more traditional encounter style and the idea of different types of enemies, even if the Pirate Sergeant is just a modified version of the Pirate. The Pirate Sergeant’s higher AC and HP shows the party they have to consider each enemy differently.

Optional: Short Rest

I didn’t originally include this in my campaign, but this may not be a bad place to include a short rest. Narratively speaking, it’s not going to make a lot of sense to have one after the next encounter. The players are not going to be able to stop the pirates from sounding the alarm, so it would just be weird if they took a breather. I say optional, and not recommended, because the first two encounters aren’t really designed for them to take much damage, if any at all, but it’s good to have a rest right here if they fumbled the encounters.

Additionally, suggesting a short rest right here both introduces the concept of a short rest and provides players with a short role-playing opportunity, which in and of itself introduces the idea that role play can happen anywhere. A short rest here would also be quite useful for Warlocks, especially if they wasted their spells beforehand.


• 2x Pirate Sentries (50 xp)

• Pirate Sergeant (50 xp)

Continuing to the north along the river, the forest gets progressively thicker, and it’s starting to get dark. Up ahead, the players see a bridge that’s well lit. On the west side of the river there are two Pirate Sentries and a Pirate Sergeant. An alarm bell is also clearly visible. The trees are thick enough that setting up for a surprise round is easy, but only at a range because the river is over 50 feet across. Whichever pirate has the first turn among them, all of which are within 20 feet of the alarm bell, will move over to the alarm bell and ring it loudly. None of the pirates are actively aware of an impending assault.

(If in the rare case the party manages to stop the alarm from being sounded, adjust the quest to lower the pirates’ overall readiness from an attack. There’s no need to change the enemies, but adjust the narrative to being less alarming, affording the party the opportunity to be stealthier in their approach.)


The Lesson

This encounter is all about strategizing. It’s a situation that the players can’t win, unless they manage the most amazing rolls ever. Basically, three ranged players would need to roll a critical hit during the surprise round. This isn’t a Kobayashi Maru, so there’s no need for them to run away, but the lesson is that not everything is going to go according to plan (assuming they didn’t already learn that lesson).

What Happened

On top of learning that, my players also learned how to coordinate more effectively. They rather haphazardly tried on the first encounter, but this time they put together a well thought-out and executed plan, which they all enjoyed staging.


• 4x Pirates (100 xp)

Continuing east, the woods continue to get thicker to the point where traveling between the trees would be difficult and would easily constitute as difficult terrain. Paths, or at least deforested pathways, are the easiest way to travel. Since the alarm has been rung, there’s a risk the party will be discovered, but their options are limited, especially as it nears the end of the day. Eventually they come across a fork in the path split by a roundabout of trees. The north fork seems to just curve around, where the south fork has a path leading further south (although it, too, curves around). Based on light, sound, and smoke, there seems to be a campfire in the southwest area of the roundabout, although it’s out of view. The four pirates are each sitting on the four sides of the fire, drinking and having fun, but positioned to give them the best vantages while keeping an eye out.

The players will have an opportunity to ambush, but the pirates’ attention to their surroundings and readiness for a fight means it’s not going to be a surprise round.

The Lesson

The players need to know that just because they get a drop on someone doesn’t mean they get a surprise round. Surprise rounds come with catching them unaware. Being positioned as they are, the pirates can see attacks coming from all angles and are ready to react quickly. It’s also a step up in challenge having a fourth enemy to contend with. Not a huge step, but enough that it starts to make a difference.

What Happened

The first thing that happened was my Forest Gnome Ranger made a huge clutch move. She argued that being a Forest Gnome, whose Favored Terrain is forests, she would easily be able to make her way through the little island of trees, no matter how thick. That gave the party an opportunity to scout out the pirates’ locations to be able to better plan their attack. It doesn’t seem like a lot, but that allowed the party to position themselves to be able to be in optimal locations for a more coordinated attack and minimized the needed distance to cover for the melee players.

The other thing that happened was the last pirate standing just wouldn’t go down. For whatever reason, the players couldn’t hit her, and she was just dancing around them, slashing them to pieces. My healer NPC was knocked unconscious, and the pirate tore through their hit points with ease. Eventually my Dragonborn Paladin hit her and hit her hard, giving her the campaign’s first, “How do you want to do this?” I know it’s a thing from Critical Role, and I try not to just copy things that are famous, but I firmly believe in its effectiveness for player satisfaction, especially after an exceptionally emotionally exhausting encounter. My players appreciated the catharsis that it gave them.

The Long Rest

After the last fight, it’s clear it’s gotten too late to continue, everyone is exhausted. It’s time to sleep and continue the fight in the morning. After hiding the bodies, the players set up camp at the fire where their enemies just were.

This is a prime opportunity to give your players another opportunity to role play amongst themselves.

Leveling Up

The last encounter gave the players enough experience points to level up to level 2. Now is a great opportunity for players to read about their new skills and spells, and select them if necessary. Make sure they do everything associated with leveling up.

The Lesson

This lesson is all about two things: how long rests work and the importance of taking shifts. New players especially should be instructed on the mechanics of long rests and the role of how taking shifts works. Now is a perfect time for that lesson because the party is in deep enemy territory on a pirate island after an alarm bell was rung. To say the least, it’s not safe for them to be leaving themselves undefended. For the same reasons, it should also be highly suggested that they sleep in their armor, which is probably best whenever there’s a strong risk of being ambushed.

What I Learned

Make sure all of your players have done everything associated with leveling up. Literally work with them one on one to make sure they’ve done everything and they understand everything. My Wood Elf Rogue never increased his max hit points, which I didn’t know until about mid-way through the boss encounter.  He was one of my old new players, so I was less hands-on with him. That was a mistake on my part. For the whole tutorial quest, make damn sure everyone is up to speed on everything, even if you come across as overbearing. If you have experienced players in the party, lean on them a little, but verify that the new players are set up properly.


• 2x Pirate Thugs (200 xp)

As the party is getting up, two Pirate Thugs set upon the party and ambush them. Have every player make perception checks during their shift, but the perception check on the last one is the one that matters. The DC should be 10. Pirate Thugs aren’t exactly known for their stealth. If the last perception check passes, there’s no surprise round. If it fails, then the Pirate Thugs get a surprise round.

The Lesson

It comes down to the idea that anything you can do, they can do, too. If you can ambush the enemy, the enemy can ambush you, too. If you can get a surprise round on them, they can get a surprise round on you.

This also introduces much tougher enemies. With an AC of 11, they’re not hard to hit, but 32 hit points is pretty meaty for new players. It also comes at a time where scaling is introduced. Higher levels means stronger foes.

What Happened

For whatever reason, my players decided that the NPC healer I created should go last on the shift and be by himself, despite there being an Elf in the party that could’ve added a little overlap for a squishy character. It was doubly worse because I rolled a natural 1, quickly teaching them the lesson that a surprise round can happen to them, too, and what can happen to players when they’re prone. I chose to not apply the unconscious rules. I’m not sure if most DMs would’ve done that in my shoes, but I felt it a bit much for new players.

Pirate Crew

• 2x Pirates (50 xp)

• Pirate Sergeant (50 xp)

• 2x Pirates (50 xp)

Having successfully staved off an ambush, the party continues west. As they do so, the trees begin to thin out again. It would seem they have crossed over the middle of the island. Eventually, in the distance they see a few pirates who are clearly waiting there for the party and have very clearly seen them. The Pirate Sergeant calls out to them and lets them know there’s no escape. As the party approaches, the Pirate Sergeant goads them to coming closer for negotiations of the party’s surrender.

When the party gets close enough to the known pirates, especially the melee player characters, the two hidden pirates jump out and start attacking the support players.

The Lesson

This encounter teaches the concept of enemy waves. It also shows how enemies are going to use tactics and traps, too. This isn’t a video game. It’s not an AI controlling a bunch of random NPCs with vaguely different skill sets. There is another real person considering the best way to win, preferably based on actions true to the enemy. Players need to be aware that they can’t just walk in and smash things in the face.

What Happened

In my game my Gnome Ranger took a serious beating. She was comfortable sitting in the back taking pot shots at the Pirate Sergeant, but I swooped in and almost dropped her entirely. She definitely learned the lesson that just because she’s in the back doesn’t mean she doesn’t have to pay attention to the battlefield  They all became aware that I wasn’t going to play things dumb, either.

Short Rest

Having been ambushed twice, and (likely) suffered quite a bit of damage, now is a good time to sit down for a short rest. The area where the hidden pirates were originally at is likely the best place to stop.  This is another great opportunity for players to have a short role-playing interaction.

Last Stand

• 2x Pirate Thugs (200 xp)

• Pirate Sergeant (50 xp)

As the party continues westward, the trees continue to thin out some and the road becomes more defined until it starts to become cobbled. As the party approaches, they see a large gate with a 40-foot tower on either side. Standing right in front of the gate is a Pirate Sergeant. As soon as the party is within range, a crossbow bolt flies at one of the players, barely missing them. Suddenly a Pirate Thug becomes visible on top of each of the towers.

After the fight is done, the players must find the hidden switch or puzzle that unlocks the gate.

The Lesson

The main lesson here is about making the players aware there will be times when they’ll be fighting at a disadvantage, or that parts of their party may be rendered ineffective. In my game, after the Pirate Sergeant was defeated, the melee characters became largely ineffective, leaving my Ranger and my Rogue to trade missiles with the Pirate Thugs.

The second lesson is introducing the concept of investigations and possibly puzzles. It should be super easy to find or complete, like a DC 5 investigation check, but the idea is to introduce the concept for new players.

Optional: Short Rest

This is purely optional, but highly recommended. The campaign is designed for the players to have just gotten to level 3, so everyone should have their archetypes by now and everyone should finally be getting their cool stuff. Also, the players just finished a tough fight, and they’re about to hit the boss fight, so giving them another chance to top off would be nice. Assuming nice is what you’re going for.

Captain Jack

• 2x Pirate Thugs

• Pirate Captain

Continuing to travel further west, it starts to become apparent that the party is getting close. Little huts and houses start to pop up and a little pirate village is formed. In the distance, a few pirate ships are docked, and standing in front of what is very clearly the flagship is Captain Jack, flanked by two Pirate Thugs. Captain Jack sees the party coming down the road and calls them out. He’s not stupid. This is clearly the work of Malcolm Reynolds, and the party is no doubt his wild card. Captain Jack wastes no time waiting for the party. He and his thugs immediately move forward to engage.

The Lesson

This is a boss fight. A boss fight is a fairly ubiquitous concept, so no specific lesson is learned. Having a CR 2 and two CR 1/2 enemies for four to five level 3 characters is going to be a serious challenge. If you don’t drop at least one of your players, you’re doing it wrong. Optimally, the party should barely make it out of there alive. This is designed to be a hard-fought battle. You probably want to avoid a TPK or you run the risk of disenfranchising your new players, so it may be necessary to spread things out if you have to, possibly leaving the healer alone unless the encounter is looking to be too easy for them.

What Happened

I wouldn’t say it was as hard fought for my players as I had hoped, but that’s largely because I rolled quite terribly. Still, I managed to drop my Wood Elf Rogue, and that included my Dragonborn Paladin’s use of Bless that turned out to be the MVP move of the entire quest. It could’ve been harder, and I’m somewhat disappointed they didn’t get to experience as brutal of an encounter as I had hoped for. The most memorable conflicts are the ones that are hard fought and hard won.


This is a pirate adventure, so there’s an opportunity for lots of treasure. It’s a great excuse to give your new players a few extra magical items and a bit more gold than they’d normally get, which you can point out in the next quest that nets them a broken saber and not much else. It also offers a little bit more enticement for the new players, and you can customize what you give them based on their class. Pirates aren’t exactly known for being picky on what they get, and it just so happens they have stuff your party could use. Plus, the smuggling ship crew is going to take the bulk of the treasure, and you can narrativly have them give the players whatever you want.

After the players get their treasure, Malcolm offers to take them back to Raven’s Peak before they go to the Halfling village. Whenever they make it back to Raven’s Peak, if you choose to have an adventuring guild agency, that’s who would ask the party to join after the impressive feat of taking down Captain Jack.

The players also have the option of going to the Halfling village, and have some adventure from there.  No matter where they go next, with the help of Wash captaining it to their first destination, they can take one of the pirate ships, assuming they think of asking. Captain Jack’s flagship is a Warship, where the others are sailing ships.

What I Learned

I think I learned two major lessons. The first is the importance of streamlining role play. This isn’t to say that it needs to be short. There’s no stopping it from still being hours long, but role play not lead by the players needs to be succinct and to the point. It needs to exist to set players up, whether that’s for their own role-play choices, for combat, for shopping, or for adventuring. Don’t say in 10 words when two will do.

The second is that part of the DM‘s job is that of player management. In the first encounter, when my players spent way, way, way too long interrogating the Pirate Sentry, I should’ve cut that off early and just told them this was a waste of their time. I did a poor job of making sure my players had their characters under control. It seems so obvious to me now, but none of that, and more, just didn’t occur to me. Granted, that is the point of this series, so other new DMs can learn from my mistakes, and maybe make fewer of their own as they try to figure out what they’re doing just as blindly as I am.

Have fun, and stay nerdy, my friends.

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Joshua Brickley

Despite looking so young, I'm in my mid-30s (36, to be exact). Up until I was 21, I focused a lot of my attention on stage acting, mostly local and school theater. At some point, I felt a need to change my life's direction, so I joined the Air Force. After 10 years, where I was an Intelligence Analyst and Mission Coordinator, I was medically retired. I went back to school and got my Bachelor's in English, focusing mostly on literary theory and rhetorical criticism, at the University of the Incarnate Word. In this next chapter of my life, I'm turning my attention towards tabletop RPGs.

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