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10 More Island Encounters

The party has faced all manner of dangers, from living islands to volcanic ruins. They might believe the worst and strangest is behind them, but the oceans are far from done! Uncharted islands lay in wait, holding all manner of threatening oddities.

Welcome to the second part of our Island Encounters d20 Chart. As with the others, the explanations and tips under each should provide everything you need to transplant or adapt them into your own campaign.

Part 1, containing Encounters 1-10, can be found here. We also have an accompanying 1d20 Encounter Chart.

11 – Pirate and merchant crews have banded together over time, forming a floating trade post of connected ships. The ocean market is home to some of the most unsavory individuals but sells the most lucrative items.

Centuries ago, pirate and merchant factions united to form a pact. They created a ‘no man’s land’ where their territories converged, to allow for safe trade and discussion between otherwise hostile crews and captains. Ships float together, connected by bridges and walkways, to form an isolated pirate haven. It entertains visits from notorious captains, infamous bounty hunters, and charismatic black market dealers. But loyal patrons enforce peace through a strick no-violence policy.

Not every island encounter needs to be on a naturally formed island, nor does it have to be hostile. The purpose here is instead to create a unique location and one that players will want to return to down the road. It is essentially a settlement, but one that is dominated by the shadier ends of society and provides risk in every interaction. This lets you create eclectic storefronts to sell odd or magical items, but keeps it more interesting than reputable sellers. The items may be stolen or looted in raids, and players know that trading there is funding those that they would normally call enemies. It is a subtler way to give heroic characters a moral quandary.

Consider the history of the location and how that informs its dealings. It was started as a pact between enemies, meaning that maintaining it would require strict rules and guidelines. The trick is enforcing these ‘laws’ in a lawful-evil way, but shouldn’t be as difficult as it may seem. Both vendor and patron should require transparency in trading. Combat and violence should be illegal, to prevent faction wars reigniting. Most importantly, residents should enforce these rules, rather than any ruling leadership. The players are new to the location but its inhabitants are not, and they are all aware of and abide by its codes. Disobeying would mean being blacklisted and possibly named an enemy of the pirate or merchant faction they wronged.

One of this encounter’s strengths is its ability to introduce characters. Give depth to the most prominent characters that your party will encounter. Write some brief lore and history for the various clans involved, as your party will likely ask around. You only need to have some loose points prepared and be ready to improvise the rest. The presence of pirates and other immoral groups also provides opportunities for players seeking work. Unsavory folk might be looking for a temporary crew, perhaps even for one of our other encounters.

Construct your own colony with our ship pieces and mercantile tokens:

12 – A man is thrown from a cliff edge as a sacrifice. He survives the impact with the surface and calls to the party for help.

The party sails near an island’s coastal cliffs of dark grey stone. They spot shifting lights on a precipice that reaches out from the cliff-face, and humanoid shadows shifting and moving. The sound of chants and shouts begin to fill the night air before a shadow plummets from the cliff and into the waters. A man surfaces moments later, injured but alive. He calls for help from the passing ship, begging to be brought aboard if they get close.

Island encounters are an easy way to have the party interject in the affairs of small, secluded societies. The man in this encounter will explain that he was sacrificed to appease their gods, and was meant to have died. Try to flesh out his character, in whichever direction you wish. Just keep in mind that he is the first taste your players get of the island’s people and will be the basis of their assumptions going forth. This is provided they decide to help, rather than letting him drown. You can use this to your advantage by making the man untrustworthy or even a liar, to play on the party’s suspicion. He was just thrown from a cliff. Maybe they had a good reason?

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A rock overlooking rough seas is the perfect start and endpoint, and is totally free right here.

You ideally want your party to engage with the locals, meaning the man will want to return to their town. This means creating the town and, more importantly, their beliefs. There is enormous creative freedom here. You can do almost anything with it, but we will provide two suggestions.

First is the simplest: the town is under threat and sacrificed the man in exchange for divine protection. This works well for a town stuck in tradition, with the man urging them to take more practical action. The players will most likely need to convince the town leaders to believe the man and oppose the threat themselves, with the party’s help. The enemy in question could be pirates using disguises to take advantage of the town’s superstitions. It could also be something more magical, such as a rift between planes. Keep in mind the stubbornness of the elders; if the party succeeds, they may believe that the sacrifice worked to bring the party to them.

The second option is slightly more intricate and may involve less combat. A corrupt hierarchy within the town could be taking advantage of the beliefs of the populace in order to maintain control. They use their positions to live affluently, while the people below them struggle to provide for their families. In this case, the man would be a dissenter, knowing the truth of the elite and speaking out against them. The nobles convinced their people to sacrifice him as punishment for his disruptions, but now he returns to stoke a rebellion.

13 – A trafficking ship full of dangerous and exotic beasts was shipwrecked on shore in a storm. The ship was destroyed and released all manner of beasts into the area.

A violent storm raged through the night, almost throwing the party’s ship against the shores of an island. In the morning they find another ship that was less fortunate. It was torn apart against the rocks and sand, and the remaining crew now call for help. Arriving on shore, the party spots strange and varied tracks all leading from the ship and into the forests nearby. They also find evidence of dead crew, riddled with claw and teeth marks. The survivors realize they cannot hide the truth, and instead ask for help in collecting the escaped creatures.

One way to design your own encounters is by looking at other settings and translating them to your own. The basis here is taking one of our previous ocean encounters and converting it to an island encounter setting. We are using the animal traffickers in this instance. Instead of the previous encounter’s beasts breaking out on board the ship, the whole vessel has been wrecked on a shore and they have escaped. This changes the environment from the bowels of a ship to whatever island terrain you wish and introduces new obstacles. The crew is still alive and the animals are panicked, and now rampage through biomes they do not understand.

Half of a ship, freshly wrecked on shore? Just add some survivors and tracks to our shipwreck map, found here.

The most obvious decision here is the types and number of beasts. They can be as varied and exotic as you wish, but should each provide a unique threat. Think about how they would each react to the area they are in, as well as to each other. Some may fight each other and local wildlife for dominance, while others may even form packs. The surviving crew is unlikely to be forthcoming, so the wrecked ship and tracks allow you to inform your party of what they may face. More information should be available as they get closer to each beast. Remember that the creatures should be panicked by their surroundings, likely stirring them into a frenzy. If you want to create more urgency, a defenseless town may be nearby.

Your party’s second challenge is dealing with the remaining traffickers. The conversation will depend largely on the characters’ morality, as the crew should not initially want to compromise their goal. They want the animals back alive, believing they can still be sold. Accomplishing this may mean offering the party a cut of the pay, and ensuring their silence. Turning down the offer means the party will need to deal with the crew. Do they leave them there, or take them as prisoners and deliver them to an authority? Be sure that this option is still rewarding. The simplest options are either by looting the wreck and crew or as thanks from the town.

14 – The skull of an old and powerful beast rests inland from an island town. Its will is restless and is slowly gaining control of the townsfolk.

A great behemoth was drawn to an isolated island and slain in ages past. Its body has long since rotted but the magic of its spirit remains. The power seeps into the minds of those that have settled nearby, influencing them in strange ways. The party arrives in the dock, quickly realizing something is strange about the people. Their wills are weakening to the influence, and the answer to their ailment lies in the old beast’s bones.

A personal favorite moment in any encounter is when my players realize something is not quite right. The encounter on this island does this through what you might call a ‘Lovecraftian-lite’ atmosphere. The town appears perfectly normal from a distance, making it ideal for when the party needs to make a stop for supplies or rest. The longer they stay there, the more obvious it becomes that the townsfolk are… off. How this manifests is up to you. They could be emotionless or inversely quick-tempered and volatile. Perhaps they implore the party to stay, bribing them with food and shelter. Try to emphasize the singular hivemind controlling them by repeating tone and behavior between different townsfolk. You might also wish to use a repeated ‘catchphrase’, having more and more people use it as the players realize something is wrong.

What form the beast takes is less important in this encounter, but its intentions are key. It may have a specific agenda that it is controlling the residents to accomplish. Maybe it requires a certain number of souls in order to regenerate itself and uses the townsfolk to attract more. In this case, include a handful of characters that have fallen into the trap, such as pirates or soldiers. Their presence should be unusual, to draw the players’ attention. A simpler option is to have the enchantment be the creature’s undying rage spilling into their minds and sending people into violent frenzies. They might otherwise be in emotionless dazes, and not remember their outbursts. But the rages might be growing more frequent, giving only days before the inhabitants all kill each other.

The dungeon area of the encounter need not be too large, as the town itself will take time. Focus instead on the atmosphere, and have skill checks for players fighting the telepathic corruption. Failing might hinder their focus, affecting spellcasting, forcing them into a rage, or eventually imposing exhaustion. You might wish to include a climactic fight before the influence can be broken, particularly if the affected townspeople are non-violent. An effective option is a magical manifestation of the beast. An elemental could rise from the blood of our Skull Cave map. You could also use an encounter we have personally played, in which mirrors of our characters appeared, mimicking our abilities as we used them.

Solving the problem after the fight doesn’t need to be complicated. Victory in combat should temporarily weaken the influence, and history books in town can provide a ritual to lay the entity to rest. Its spirit could alternatively be either banished or bound to an object. Requiring the players to seal the monster in a piece of gear could introduce a unique cursed item, with a story personally tied to the party.

15 – A group of faeries controls an island, luring unwary travelers. The illusion of a town draws the party in and illusions serve to divide and deceive them.

An idyllic island of magnificent groves and springs is home to a colony of fey. They act as sirens, conjuring illusions of what visitors want most in order to trap them. The party finds themselves drawn in and lured apart by separate groups of faeries. Faeries conjure all manner of illusions to make them comfortable and content, and to hide the bodies of those that have come before.

This is, in many ways, the reverse of the previous island encounter. Unlike the last, the purpose of this encounter is much more character-based. The fey do not need to be malicious, but rather amoral tricksters and pranksters with an inherent misunderstanding of mortals. Their exact motivation is up to you. They may simply wish to use their captives as playthings or subjects for their fun, or they may be studying them in their own way. There is even the freedom to have them be beneficent, using their own strange methods to help the characters face whatever may plague their minds.

The faeries’ illusions will be used to demonstrate their goal. It should start with an inviting setting, such as a town or market. You want the party to be comfortable, feeling safe and unwittingly allowing the fey to divide and conquer. How quickly the trap is revealed will depend on your chosen illusions. The faeries may maintain the ideal setting while playing small tricks, like stealing trinkets or moving objects. They may also reach into characters’ memories, pulling them into illusions crafted from the pivotal moments in their lives. This option allows you to run an encounter that delves into backstories and motivates character growth. Keep them somewhat vague and dreamlike if they become visible to other players, as the detailed explanations should come from the party member in question. Your goal is to prompt some more impactful party conversation.

The possibility of a final confrontation will depend on player actions. Overcoming the illusion would reveal the faeries themselves, but may also unveil the bodies of those that previously fell into the trap. This does not mean the faeries are evil though. As their morality is inherently different to our own, they may view it as the people having lived in bliss until their final moments. The victims may have likewise faced moments from their past, but failed to overcome them and instead became trapped. The fey may understand that the blame falls on them, but believe that the possible positive results justify the risk. Players may opt to attack, but you should make the decision difficult by emphasizing the faeries’ inhuman nature. In addition to character growth, you may wish to reward them with some of the trinkets collected by the fey.

16 – Explorers speak of an ancient ruin on a strange, drifting island. Those that have seen it have not returned, as the ruin is actually the mouth of a great beast.

Stone teeth encircle the beast’s disguised maw. We have a great map for the mouth’s opening here.

The island is small and peaceful, home to a single ruin carved into the ground. Many have attempted to reach and explore its depths, but all have been famously unsuccessful. None have survived the trip. The party now finds the site, a pit extended too deep to see and surrounded by strange rock formations. As they descend, the stone walls gradually change in texture and appearance. Carved masonry turns to flesh and the adventurers quickly realize they are dangling themselves into the throat of a behemoth.

This island encounter acts as another play on the ‘living island’ concept. It is similar to our hostile version of encounter 2 but disguised to appear closer to encounter 1. This does bring the common problem of having to attract your party to the location. You might lure players with simple curiosity or the renown connected to rumors and stories of the island. Others might require further incentive. They may be in search of a resource from the ruin, without realizing it is one of the beast’s organs. The party may also run into the spouse or family of a recent explorer, who begs them to find a missing relative. If they encounter the island randomly, a single member of the exploration party could be calling to them from shore. His group has been gone much longer than they planned, and he needs help recovering them.

The climactic moment of the encounter is the players’ realization of the truth, which makes it important to build up to that moment. The beast has intentionally taken the form of natural elements, turning its mouth and teeth to stone. You want your description of the surface to create tension, but not reveal anything. Note the shape of the pillars, but keep away from any mouth-related terms. As they get deeper, however they decide to do so, you should slowly describe the walls changing. Try not to directly label it, but instead tell them how the stone becomes smoother and appears wet. The walls will eventually pulse slightly, and veins may even appear if they repel deep enough.

A trap should be sprung to prevent your players from escaping without challenge. This works best with lower-level parties who do not have access to higher-level Fly spells or similar utilities. The beast’s mouth may be filled with a corrosive mist that eats through rope and puts the characters on a time limit. Remember, it has evolved to hunt this way and to do it effectively. This does mean that you need a way for players to escape. The exact method should relate to their goal in exploring down, and should ideally be hinted to them before they take the risk. They are more likely to make an attempt if they know that succeeding will also allow them to escape.

17 – The island’s shore holds a cliffside altar, activating to open a portal. The party must venture within, but what lies on the other side?

Steep, rocky cliffs form harsh walls along the shoreline. The party follows them, eventually coming to some sort of ritual site containing two crystals and a gate-like structure. They are able to reignite the crystals’ magic, conjuring a portal that connects the site to a mirror of itself in a distant tundra. The players must proceed further but are unprepared for the opposing climate. Worst of all, the crystals crack and chip against the magic’s strain. The portal won’t last forever.

One of the many ways to keep your players on their toes is to present them with an unexpected climate. Shifting from tropical island encounters to snowy mountains introduces new environmental dangers and wholly different creatures to face. To attract your players, you may wish to have a sinking ship call to them for help. The survivors will speak about their attackers, who fled through the portal with valuable items they stole. The party may alternatively take a contract to retrieve an item from the other side. Monsters could also be finding their way through the activated portal, requiring the party to close it. A nearby town being threatened by these creatures should hopefully be enough to motivate them.

Where or what is on the other side of the gateway will likely depend on the party’s purpose for venturing through. We would advise a destination as different from the entryway as possible, such as the snowy fields or mountains mentioned above. Your players will have to battle the elements to find their quarry, whether it is reaching a location or tracking thieves or raiders. Include more exotic monsters themed around the new locale. Pursuing thieves may lead to a larger outpost of enemies far more knowledgeable about the area than the players. You can add tension and risk by clearly show that the portal cannot be sustained indefinitely. This also puts a limit on how long the party has before they must return. Just be ready to provide a second chance, at a cost, in case they fail.

An interesting element you may wish to include is a friendly settlement on the other side. Conversation with them can allow players to learn about the portal, particularly if their goal is closing it. The historian of these people can then point them toward finding the item they need. We would suggest also adding a climactic fight to the encounter. The locals might tell them that the portal was actually created to banish a beast to the island and it now rises to crawl back through. The skeletal dragon animates as snow beasts attack, forcing players to fight on both sides of the gateway as the sealing ritual is cast. They must focus on playing around the portal, with two teams defending mages on either side. The snow combat is a battle of attrition until the gate closes, allowing them to rejoin the island team and defeat the dragon.

Battle Map: Volatile Portal map collaboration banner
This encounter is specially designed for use with our Volatile Portal map, created as a collaboration with Forgotten Adventures. It’s totally free to download, comes with skeletal dragon tokens, and can be found here.

We also have a variety of snow maps for whatever waits on the other side…

18 – A colony of goblins has made an island their home. They are unaccustomed to visitors and treat the party as prophesied heroes. But they also have a tendency to sacrifice their ‘heroes’.

Long ago, a ship wrecked against a small island. A small group of captive goblins survived to lay claim to the island. This same tribe flourishes generations later, in a society secluded from and forgotten by the outside world. The party finds themselves on the island and the natives greet them with reverence and luxury. Goblins give them thrones, beds, jewels, and everything else they have to offer. After all, the goblins’ ritual dictates that the more comfortable a sacrifice is, the greater the gods’ appreciation.

The concept for this is Jack Sparrow’s own island encounter in Pirates of Caribbean: Dead Man’s Chest, but with goblins. It is relatively simple but lends itself well to a comical and memorable reprieve. Your choice of introducing the encounter will come down to context. Once again, the simplest answer is placing something the players need on the island. You might prefer to use our list as a random encounter chart, in which case you can have a great storm or similar threat arrive in the night. The crew could appeal for shore leave to resupply and repair, and the dock of a lone island has just drifted into view. Perhaps the goblins’ prophecies speak of a group that arrives in the wake of a storm, to then be sacrificed to the sky god?

We have the perfect goblin ritual site, found here. If you’re a Patron, you also get access to our night variant!

It is important for the locals to be as welcoming as possible, as players are naturally skeptical of goblins. Have them offer the party everything they need and invite them to stay the night and eat with them. They will shower the party and crew in luxuries as the day progresses. Insight checks will reveal that the goblins are not actually lying, but seem strangely excited by their presence. A small group should be visibly preparing their ritual site for the night’s festivities, and walls, murals, and texts should be available for players to learn about their traditions. Just try not to give away exactly what will happen. Lay clues of the truth, as the goblins might believe the party is willing and came to them specifically to be sacrificed.

The final reveal should only come as it is in the process of happening. Goblins should take the party to the ritual site at night and give a grand feast. They will dance and chant in their own language, though a party member that investigated the earlier texts might translate a few key terms. The exact trigger is up to you. The goblin elder may cast a spell that magnetizes the party to their ritual stone. Alternatively, a god may actually respond to accept the offering, forcing a three-way conversation. Goblins will argue that the party is a willing sacrifice, while the god in question will try to understand the situation. What follows will depend on your players, so be ready to improvise while remembering to focus on humor and fun.

19 – Sahuagin have encircled an island, forming a blockade. The people of the island can defend from attacks but rely on trade for resources. They won’t last much longer.

A naval ship in the harbor had reinforced the already defensible coastal town. A large battalion of sahuagin had attacked the town but were driven off. They now wait in a ring around the island, preventing supplies or reinforcements from reaching their prey. Sahuagin attack any ship that attempts to, and the party finds themselves becoming the next target.

The key to this island encounter is setting the stage and letting your players decide how to proceed. First, you should make the situation clear. Sahuaging will attack the party’s ship if they try to reach the island. If they plan to bypass it, simply insert a merchant vessel nearby and have the sahuagin raid it. The party will need to defend it, and speaking with the crew can help inform them of the situation. Their actions from that point will determine the encounter’s path, so your focus is planning what is happening in the background. What is the town’s plan, and how are they going about it? What troops do the sahuagin have and what are their tactics?

Sea Monster Tokens RPG assets, Preview
Sahuagin, sharks, a hag, even an aboleth! Our Sea Monsters Tokens are free to download here. You can even color your own by using our Token Editor!

The sahuagin are intelligent, and should therefore have intelligent motivations and actions. They are starving the townsfolk to weaken them, but what is it they want? You are free to simply make them malicious raiders, hunting for food or valuables. They may also be using the town as some sort of offering to a god or to summon a great monster from the depths. Try to make their motivations clear through their actions and their leader. Raiders might be led a larger sahuagin berserker, riding atop a vicious ocean beast. If their purpose is magical, a shaman or group of mages may lead them or act as lieutenants. Ending the blockade will require routing the leader. Otherwise, the commander will spearhead their second attack once hunger has sufficiently weakened the defending soldiers.

Give equal planning to the island’s residents. The players may decide to breach or sneak through the blockade in order to acquire allies and fight their way out. The people of the island should have their own plan and will likely have rallied around and follow whoever came up with it. Develop several characters of interest, perhaps giving them conflicting ideas for survival. One of these will most likely be the naval captain. The general populace should be emphasized as panicked and volatile, as their supplies are near to running out. There should be a clear time limit before the second attack. From there, try to progress the situation to give players freedom in commanding the remaining forces and controlling the use of resources. The town’s fate is in their hands, so try to accommodate their chosen plan (within reason, of course).

20 – Few know of the hidden arena, sequestered on a secluded island. Fighters travel from all corners to compete and prove themselves.

A ring of harsh mountains covers the island’s surface. The inhospitable terrain and lack of trade access have prevented settlements from being established, though several different rumors speak of the area. Only those involved in its true purpose know what lies within. An unknown group constructed an arena centuries ago in secret. Mountains of stone and illusion hide the fighting pits, which were erected to test the land’s greatest warriors. Invitations go to those with a reputation for strength, and only those with an invitation may enter.

Inspired by Assassin’s Creed: Odyssey’s Pephka Arena, our final island encounter introduces a rewarding and repeatable landmark. This encounter works best once the party has made a name for themselves, but is able to be reused and reintroduced throughout the leveling process. The first design step is its initial appearance. This is perhaps the simplest of all our encounters, as it can come in the form of a letter. A courier may deliver it in town, or the letter can appear from a magical rift that appears on the deck of the party’s ship. Or combine both, and have a magical courier teleport to them, hand it over, and teleport away. When the party approaches the island, holding or using the letter in some way should reveal the path inside. One idea is an illusory cliff, with only those possessing the invitation being able to see and pass through.

The obvious focus of the arena is the fights themselves. Populate them with a variety of fighters, but don’t feel the need to build characters and backstories for every one. Choose a number of the most difficult, that the party will be able to face as they gain levels. Give each of them unique tactics and gimmicks. The rest need only be collections of grunts to give the party a moderate challenge, with enough varied abilities to keep it unpredictable and interesting. Make sure that players have a way of knowing the difficulty of the fights so that they have an idea of what they’re getting into. If they overestimate themselves, be sure to give them a way out, be it surrender or unconsciousness.

A single pitmaster should act as the announcer and manager. The party will speak with him or her to choose their combatants, the number of fighters, and most importantly, to place their bets. The other top-tier fighters should be accessible for conversation, but don’t need to all be there at the same time. They have lives, after all. If you used one, have the courier appear. You may wish to include a code of conduct similar to encounter 11. Violence might be outlawed outside of the arena, with the punishment of blacklisting. This means conversations won’t erupt into combat, but also allows you to use characters that the party would otherwise not speak to. Your campaign’s villain might pay a visit to watch them fight, knowing that the arena’s laws protect them. Outside lives are for outside of the arena, and willing combat settles all disputes.

You can find our own arena map here, or become a Patron for access to our arena tiles to make your own!

What’s Next

That concludes our list of Island Encounters. We hope this gives you something for use in your own campaigns, whether you use them directly or just find inspiration. And if you want a convenient way to use them all, maybe try our Island Encounters d20 Chart. Either way, we would love for you to comment with feedback or any ideas they give you. We would be especially excited to hear any stories of them playing out in your own games, and how your players react!

Suggestions are always welcome for any other maps or settings we could design encounters for. We plan to move inland with the next, but we’re always open to hearing what’s popular or wanted.

If you’re new and starting off with our encounters, also take a look at our various hand-drawn maps and assets. Maybe pay a visit to our previous d20 Chart of Ocean Encounters.

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