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Between the larger countries and continents are countless smaller islands. The party’s oceanic travels have them passing many of these. Most are innocuous and either barren or sparsely populated, but there are some that draw attention. They spend much of their time addressing these threats, but even more is spent outside of them. There is much for the adventurers to do.

Following on from the same addition to our ocean encounters, we bring a detailed tutorial on how to structure and run island-hopping adventures. Our purpose here is to assist in running island adventures, particularly those using random encounter lists. We want to simplify the process of connecting encounters, as well as handling travel and pacing within them. Player-driven downtime during travel is a key part of the game, full of opportunities that are commonly overlooked. Our aim is to help you make effective use of that time, without taxing the timing or structure of your campaign.

1d20 Island Encounters

All of our tips and advice are designed to work with any island-based campaign. To assist further, we also have 20 Island Encounters for you to translate into your own campaign. Whether you use them a random list to fill travel time or develop them into larger, sprawling adventures, our list should prove useful. They are written with the purpose of inspiring and teaching, to maintain the feeling of personal creation when using them. They can be adjusted for any party or campaign. Give them a look and let us know what you think.

Encounters by Environment – Islands

Looking for everything in one place? We’ve also brought out a series of ‘Encounter by Environment’ PDF’s, to cover everything needed for running encounters in the specific environments. They include our ‘How to Run’ articles, such as this one, as well as the combined encounter lists. For maximum convenience, each download also includes a handful of free and appropriate maps and tokens.

Part of a Larger World

Island adventures, by nature, are extremely similar to oceans. This means that most of the points from our previous ‘How to Run Ocean Adventures‘ still apply here. Fitting the oceanic stretch of your campaign into the larger world means considering the context and emphasizing integration. The state of your world should be reflected in the locations and characters present. You want to prevent your oceans and islands from feeling isolated, save for encounters that make specific use of it. Likewise, make use of your party’s position on their ship when handling encounters. Give them specific roles and require them to interact with the crew in a way that befits their station. Leaders’ responsibilities differ from their crew’s. For more in-depth instructions in doing this, refer back to our previous article.

Remote, but not Isolated

Seaside Precipice RPG battle map, color
Don’t pressure yourself into designing entire island maps. Focus on your points of interest, like our Seaside Precipice, found here.

Some of the aspects of creating context are more important when using island encounters. One of these is non-player character knowledge. Unlike random encounters when sailing, islands are locations in and of themselves. Their size and general prominence in an area will often lead to people knowing about or spreading rumors of them. This plays into creating narrative hooks for players. Use teasing mentions of future content when they are onshore and conversing with locals. These lures only need to be loose tales, stories, or overheard conversations, the purpose of which is to pre-integrate them into the world. Create the connection early, before they even reach the encounter. Players may also then choose to seek them out, which streamlines your job of choosing encounters. There are other methods that work better for random encounters, which we will cover a little further down.

The connecting of islands to the larger environment continues when players reach the destination itself. The key point here is the consistency of climate and terrain. Parties sailing through tropical waters are unlikely to stumble across an iceberg. This example is used, in particular, because it highlights exceptions to this rule. Certain encounters, such as our Island Encounter #3, are designed to generate curiosity through the use of wildly different terrain. The sudden change acts to catch their eye, though it is best to reinforce this with another incentive. It also provides unique challenges within the encounter. Having the climate gradually change as the party travels is also a great way to display the distance they are covering. Mix weather and temperature changes into your travel descriptions. The islands will then acting as tangible displays of how far they have come.

Quiet Moments

Downtime in your island adventure is, again, very similar to any other ocean travel. The key is to let your players make use of the space they have on the boat while still requiring them to handle their responsibilities. Have them make checks depending on what they choose, allowing them to work on crafting, gaining proficiencies, or assisting travel. This will change depending on their level of authority. Certain dedicated positions will have them tied up in maintaining the ship or other tasks, with their own rolls. Remember to make use of the crew and have them converse with the players in longer stretches of uninterrupted sailing. This works to help alleviate the feeling of ‘fast travel’. Try to have each stretch of travel feel different from the last to avoid monotony.

Between the Beach and Battle

In truth, the length of most island ‘encounters’ makes them more akin to individual, smaller island ‘adventures’. They rarely involve parking the ship, fighting something, and then sailing into the sunset. This means that many have their own form of downtime while on the island in question. It may not be far, but the transit from shore to destination should involve a running description of the terrain and points of interest. Try to emphasize the tone of the encounter, whether that be inviting, unsettling, or outright dangerous. Otherwise, this time serves to let your players prepare and learn.

For encounters that create tension through ongoing danger, like Encounters 4, 9, etc., consider having it extend over a night’s rest. Have the island adventure act like any other terrestrial quest in a hostile land. Maintain the tension and sense of danger in the environment. In quieter moments, give players choice in how they travel and defend themselves. Things like stealth and perception checks are paramount in enemy territory. The exact details will vary with each encounter, but your job should always be to emphasize the atmosphere and shifting environment while providing resources for your players’ choices. Create the canvas for your party to act upon. From there, your job is creating the reactions and consequences.

Local Guides

Many of our island encounters make use of instigating characters or even entire settlements. Let your players control these interactions to gather their own information rather than dumping exposition on them. This can all happen in the time between their arrival and when the encounter really kicks off. Putting your players in control gives them agency and grants you time to create atmosphere through other characters and surroundings. Writing and playing these characters will be unique to each encounter. Try to concisely show the encounter’s theme and source, as well as the context of the island (their society, structure, etc.). The underlying issues or danger should be teased organically throughout the interactions. If they are panicked, show it. If they are enchanted, have them be slightly unsettling. The idea is to tip players off and incentivize them to take the initiative and investigate.

This is much simpler for encounters with a singular character or group asking for help. In these cases, simply let your players handle the questioning. You only need to give the characters a level of depth equivalent to their number and how long they will be present. If they will be accompanying the party for some time, try to make them interesting and distinct. If the party is joining another group, it is better to focus on a small number of them. You would rather have two memorable faces than the same number of personalities spread over eight different faces.

Shipwrecks are the perfect lure for passing adventurers. If our Shipwreck battle map lures you, give it a download. It’s 100% free and can be found here.

As Danger Arises

Transitioning from traveling into your island encounters is very different from regular random encounters. As mentioned above, the stops in your island adventures will tend to be much longer and more significant. This means it is a good idea to tease several of the encounters before the players embark on their journey. Make use of bounty boards, authorities, and general hearsay to clue your party in to what they might come across. This should not apply to every encounter, as that would only serve to overload players with knowledge of every danger ahead of them. If you are planning on using multiple islands, try grouping them together. Change the rumors to instead speak of the number of unexplored and mysterious areas. Mention one or two of the most unique, and give a warning of a particularly prevalent enemy faction (sahuagin, pirates, etc.).

There are two archetypes for encounter introductions: sudden occurrences and slow builds. Islands can make use of both, depending on their content. The key is to manage the correct tone and pacing for each one. The former is designed is to force players into making quick, decisive actions. Use this in the speed and inflection of your description, to get their pulses up and shift into action mode. The second example acts more like a trap and requires a little more care in playing out.

An important detail to remember is the pacing of your island adventure. You want each encounter to feel fresh and distinct from the last. Don’t use encounters that are similar to each other, or use similar introductions or enemies, in succession. Vary the length of events, connected by the aforementioned downtime, and keep your players on their toes.

Sudden Call to Action

No matter your campaign structure, it’s a good idea to have encounters that can occur randomly when you need them. This allows you to fill unexpected gaps without players realizing it. But the similarities between islands can make it difficult to hook players in. You’ll notice that many of our island encounters have hooks built-in, in the form of someone calling for help or a visible threat. These are the easiest ways to pull the party in and motivate them to get involved. Highlight the tone of urgency and immediacy. If they do pursue it, you are able to immediately make use of the encounter’s tension. You also have a character for the players to interact with, as we noted in the previous section. Use them to begin giving the party information, as well as an insider’s perspective. Their character should reflect the encounter’s tone and context.

The ocean’s naturally open sprawl means that players should have the ability to see them coming. This applies both to characters calling for help and for islands that are themselves dangerous, such as our Encounter 9. An adequate perception check can reveal that something is off, depending on the specifics of the encounter. This is a minor detail that serves to reward players for good rolls, by giving them time to prepare and decide if they want to engage. A downside of sailing encounters is often that the party can simply sail past, but that’s okay. Let them make that choice. If your game favors consequence, have that ignored danger continue to grow and become a bigger problem later. Maybe a character involved saw the party’s ship and later recognizes them?

A Baited Trap

The other type of island encounter will tend to be one that begins innocuously, with slowly building danger. You can see this used in our Island Encounters 14, 15, 18, and 4, to a lesser extent. The purpose of these islands is to use the absence of a recognizable hook. Disguise the encounters as a regular stop along the way. Once players dock, work on slowly revealing the true nature as they go about their business. This will act as a form of downtime, as we described above. Use this time to begin laying clues in the actions of locals or the environment itself. Try to put your players on edge and guide them towards investigating. The best part is that if your players don’t stop, they haven’t seen the encounter. You’re free to keep the encounter in your back pocket and use it again later.

We have a multitude of maps for creating towns, starting with our Coastal Town. You can find it here, or look through our gallery of town and city tokens.

The most important aspect of these encounter introductions is your use of tone. Let your players dictate their actions and handle it like regular downtime. They are free to purchase supplies, relax in a tavern, or explore the town. The danger is not immediate, so they can safely split up. In scenarios like our Encounters 14 and 15, use the interactions with locals to initiate the encounter. Townsfolk might speak in a slow, monotone manner, constantly invite them to stay, or watch the party’s every move. Imagine the background characters in many horror movies’ first act or the party scene in Get Out. Start off slow and make it more obvious the longer players stick around. If the effect is illusory, you can everything seem fine until they attempt to leave. The illusion can then shift to prevent them from reaching their ship.

Once the Storm has Passed

The aftermath of your island adventures will always be dependant on player choices. With that said, there are things to keep in mind. Few islands have the capacity to damage your party’s ship, unlike ocean encounters, so they will rarely be left with further problems. They should still be challenged, but success should come with rewards. Your ultimate goal is for them to sail away different from how they arrived.

For the purpose of keeping encounters fresh and unpredictable, it is best to not overuse islands. You don’t want players being able to anticipate every turn or for your campaign to devolve into ‘one encounter per island, per session’. Break them up with lengths of uninterrupted downtime for player agency. When the time comes for another encounter, think about instead using an ocean encounter. A danger in the waters can occur more seamlessly that having to make another stop. This is a simple way of varying the dangers and situations they face and avoiding monotony.

New Friends and Foes

Aside from treasures and monetary gain, a common result of island encounters is a relationship with the characters involved. The party assisting another group might result in those people coming aboard and traveling with them. Even if they do not, those characters might show up later. They will be predisposed to helping the players (provided the encounter went well), giving your party an advantage in a future situation. Your players will have a reward identifiably linked to the past encounter. This is also one reason to not overuse these kinds of encounters, to let the characters involved be individually remembered. New enemies could likewise be made, giving the players new motivations and stories. Even if these characters only show up one more time, it helps connect your campaign’s world and creates narrative throughlines.

A good practice for making encounters impactful is to have them affect later encounters. Characters that are saved from danger are a great use of this, by bringing them aboard the ship. Fighters will be able to help the party if they come under attack. Experienced sailors can help with general duties, giving player characters time off for their own pursuits. Someone with knowledge of the area might allow the party to avoid a danger entirely. This serves to show the importance of encounters and choices, and rewards players for a job well done. You can develop the characters during downtime until your players reach a port, at which point they can depart.

Added to the Map

Clearing out the Pirate’s Cover will have lasting effects. Downloading it will too, by improving your campaign. Find it here.

Island encounters (almost) always leave behind their locations. Even more than the characters, the islands themselves still exist once players move on. Consider the lasting effects of your party’s actions and where they might lead, in case they return. Dangerous or mysterious lands might draw investigation, while towns might need to repair and recover. Settlements, in particular, are a great way to reward your players for heroic deeds. The thankful residents will be happy to see their saviors again and offer them all manner of hospitality. The same goes for islands close to those that were spreading danger. Encourage return visits as your players travel and emphasize the resulting changes in your description. Using a brighter tone to contrast the first time they were there is a great way to show the results of their actions. Best of all, let the word of their actions spread and build a reputation.

Knowing my party and the habits of many others, there is also the possibility of an island not being left behind. Give the same thought to how that affects the surrounding area. Whether it was for good or ill, have it come up in conversation later. It’s sure to get a reaction from players. And people will know about it, after all, even if they don’t know who was responsible.

You don’t need to plan these changes out immediately. Make brief notes of your players’ actions while they’re there, as well as the island’s location. If you later find that your party is sailing nearby, you can refer back to your notes and extrapolate the changes in the time that has passed. Remind your players of what previously happened there and who they know, if you need to. Focus your description on reminding players of their first visit and highlighting the changes, even if they are just sailing nearby. Seeing tangible, positive results can be one of the most rewarding moments for both characters and players. This will most often come in the form of a previously struggling people now thriving. Conversely, the home of a hostile faction might show signs of disrepair, indicating that they have not returned.

Beach Dunes Battle Map, banner
Many of our maps have variants exclusive to Patreon supporters. Our Beach Dunes, found here, also has a black sand version.

What’s Next

That should be everything you need to know to fill what would often be the ‘gaps’ surrounding island adventures. You can find the same for our ocean adventures and expect similar articles for future releases. Our aim is to eventually cover every major environment so that any DM, running any campaign, can find something to help. If you’ve enjoyed this article and are thinking about looking at our other writeups, consider downloading our PDF’s. The format is much simpler, and your support is greatly appreciated.

As always, we’d love to hear any feedback you have. What do you think of our advice? Do you have any of your own? Feel free to post any comments you have on the topic!

And if you’d like to see what else we have, hop on over to our blog and gallery:

About the author

Troy McConnell

Part-time DM and author of 2-Minute Tabletop's encounters, map lore, and characters. Basically, I write about all the campaign ideas that I don't have time to run. All with the assistance of my feline familiar, Wink.

You can support my writing efforts on Patreon.

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Published: October 15, 2019

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