The Thousand Isles is a tropical archipelago , stretching over approximately 5000 leagues of ocean. It in intended as a "drop in" region to support Pirate style gameplay, that can easily be added to any fantasy campaign setting.  ...

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Skull River Bay (Map) is one of the principle pirate havens and trading centers in the The Northern Reach. Lying as it does at the far south eastern edge of that scattered and wild archipelago, it serves as the last civilized gateway into an unexplored region. It’s proximity to the more populated islands of the The Inner Archipelago to the south and the excellent harbor the bay and river provide make it an import center for trade.

The area around Skull River Bay was originally populated by the First People. The town itself began as a small naval outpost of the Annwyn Empire,  In Imperial times the area was known as a good harbor and hurricane hole and the Empire maintained a small outpost there to support patrols and forrays deeper into the Reaches. This outpost was intended to be expanded as a jumping off point for a more thorough conquest of the Reach, however when The Recall sounded, these plans were abandoned. 

During the Interregnum, the community was mostly abandoned during the general anarchy and associated economic crash, being populated only by the remnants of the original tribes and a few hardy fishermen and seafarers.

Once order was restored and the Era of Independence  got underway the island still remained an unknown backwater, though it was during this period it began its long arc as a haven for criminals and pirates.

This all changed with the coming of Mithra. While a native of Haven Towne, Mithra spent his later life as a blacksmith at Skull River Bay. It was here he had his Great Revelation and from here that he undertook his Journey Into Darkness that resulted in his deification and the founding of the Church of Mithras.

As a result, Skull River Bay became an important religious center and pilgrimage destination during the early years of the Mithran religion. It was during this time, approximately 150 years ago, that the Church of Mithra Risen, the Monastery of the Bells and the Abbey of St Claire were all built.

However, 129 years ago the Mithran Church suffered the first of its major schisms. When the Conclave of Pader ruled on several major doctrinal disputes in favor of the Orthodox Church of Mithras, the older but far less rich and  populous churches of the Reach refused to accept the ruling and splintered into the Reformed Church of Mithras. This resulted in a schism between the Orthodox Church (centered in Haven which today contains the vast majority of believers) and the Reformed Church which is mostly active in the Northern Reach and Valoria.

While the two churches refuse to acknowledge the authority of their respective hierarchies, relations between them are for the most part cordial if strained. However the Orthodox Church has gradually deemphasized the spiritual importance of the Mithran holy sites in the Northern Reach in favor of those closer to Haven and has refused to accept as canon the writings attributed to Mithras during his time in Skull River Bay (called the Books of the River).

Today the holy sites in Skull River Bay are not visited often and rarely see pilgrims outside of the local region. 


Skull River Bay’s economy is built around seafaring and Trade. As a free port, it is one of the few places in The Thousand Isles where goods and services can be freely exchanged without the necessity of providing a percentage to the local  Merchant House, Guild or some other entity  It’s Pirate Market is notorious and legendary across the Isles. In addition, while lacking a formal dry dock, the shipwrights of the town are superb at building and refurbishing the small, fast deep water ships that the Northern Reach is known for.

The town is also a notorious Pirate port. The ambiguous legal standing it exists in allows its Governor great latitude in the extent to which he prosecutes piratical activity and over the years a succession of Governors have discovered that aiding and abetting piracy is far more profitable than suppressing it.


Skull River Bay is ruled by a Governor appointed by representatives of The Republic of Haven, The Antilles, The Twins and Etmarch. The Governor serves for life and other than appointing his successor the Inner Islands have little direct authority over his actions.

This system has been in place since the end of the last The Pirate Crusade 75 years ago. This campaign occured when the governments of the Inner Archipelago finally became fed up with the depredations of the pirates of the Northern Reaches and launched a joint military operation to clear out their havens and destroy their ships. Three years of scorched earth persecution hunted the pirates lords to near extinction and also dealt severe colotoral damage to the communities of the Northern Reach

While the original intent of the charter and governing system for the town, put in place following the crusade, was to suppress piracy, it has failed spectacularly. However the signatories of the treaty (some of which benefit from the current situation) have been deadlocked in amending it. 

The town does benefit significantly from it’s official standing as “Archipelago Port”. This means that the three trading houses that own exclusive charters to trade in the Reaches cannot apply that monopoly to Skull River Bay. Normally this designation would also mean that only chartered merchant companies would be allowed to run cargo into and out of the port. 

However since the Governor generally turns a blind eye to unchartered traders bringing cargo into the town (assuming they pay the relatively high import taxes) the town is effectively a legal loophole that allows the free traders of the Reaches direct access to Inner Archipelago markets and also allows the rest of the merchant houses that don’t own a monopoly charter similar access to the Reach.


Skull River Bay is an old town, parts of which date back for over 500 years. Most of the buildings are much newer however, since the town was seriously damaged in a great Tsunami 120 years ago and then partially burned during the Pirate Crusade 75 years ago. However The Redoubt and the stone docks date back to the Annwyn Imperial era, and the Temple of Mithras Rising, The Governor's Palace and some of the other larger buildings in the center of town are several hundred years old.

There are four main districts of the town

  • The Dockside is dominated by a long avenue paralleling the docks called the Rumbala.  This street mostly consists of inn, taverns, cat houses and the like, the two most notorious of which (Bella Bell’s and Sally Brown’s) bookend the street.

  • Cathedral Square the center of town, contains governmental and religious buildings, including the grand Cathedral of Mithras Rising, the Governor's House and the Port Authority. 
  • The Bayou This part of town on the far side of Skull River abuts the great Mangrove Swamp and is wholly devoted to maritime activities like fishing and shipbuilding and maintenance.
  • The Pirate Market This is a large fairground in between the rear of Cathedral Square and the southern wall. It contains few permanent buildings but on certain days it hosts the infamous Pirate Market.


In addition to the same 17th century Caribbean inspiration of the overall The Thousand Isles, Skull River Bay draws heavily from Santo Domingo with regards to layout and geography. Tortuga and Salt River Bay, both major pirate havens in the real world, also leant much inspiration. Finally there is a bit of New Orleans and Barataria in there (which inspired the Pirate Market)


The Thousand Isles is a tropical archipelago, stretching over approximately 5000 leagues of ocean west of Valoria and north of Mbo. It contains twelve large extinct volcanoes, ten large islands in an The Inner Archipelago and hundreds of smaller ones scattered in two outer reaches

While the Thousand Isles has been populated for millenia by a polyglot of natives and neighboring nationalities, up until 500 years ago it’s society was relatively tribal, with low population densities and technology levels. That all changed with the coming of the Annwyn Empire. Unlike in neighboring Mythras, the An aggressively and extensively colonized  the Thousand Isles especially Haven Towne and the nearby major islands. The Anwyn empire used these islands as their primary naval base in the western ocean and these islands became the furthest reach of the An empire. 

When the Annwyn Empire fell, the locals were left to their own devices. After a period of social upheaval a rich polyglot maritime culture developed scattered across the extent of the Isles. 

The island populace is still sparse by continental standard, and primarily human, though orcs and halflings are numerous in the The Northern Reach, there are rumors of Tortola in the south, and giants dominate the island of Gianthome.  Elves, tieflings and dwarves are uncommon though not unknown. In general, due to their historical position as a major trade corridor, the islanders are remarkably worldly and accepting of other faiths and races,  

While the Thousand Isles are small by population and not aggressively expansionist they are consummate seafarers and far ranging traders. They have retained more of the old Annwyn naval technology then the adjacent continents have managed to do. Their ship building, metallurgy and naval warfare is well in advance of most of their neighbors, though still well behind the peak of the An Empire (mapping to roughly late 1500’s AD in our world while most neighbors are a hundred years behind that). 

The Inner Archipelago states and The Merchant Houses field large war fleets of galleys for use in the shallow water of the inner archipelago, in addition to deep water trade fleets, generally consisting of large slow galleons and faster, smaller Fluytes. These ships trade far across the wider ocean, to the Reaches and beyond. In addition small fast sloops, barks and brigantines are prolific for local trade especially in the more far flung and less populated Reaches. 

Cannon and gunpowder exist but are expensive, ungainly and still rare (roughly late 16th century equivalent). While it is not uncommon to encounter individuals sporting matchlock pistols and rifles, they are usually a mark of wealth and success or membership in a military organization or militia. Armor, melee weapons, bows and crossbows are still common fair. With regards to ship weaponry, heavier warships and larger merchants can and do carry cannon however smaller crafts generally can’t, due to both size and expense. 

Land armies contain a mix of matchlock infantry, crossbowmen, halberdiers, short pikes and other melee weapons. Since land combat is still primarily ship based, cavalry is rare as are large Tercio style formations. In general the Thousand Islanders are masters of sea combat while being generally less inexperienced in large scale land warfare then their continental cousins. 

That is not surprising as naval warfare is essential for the survival of the various states, citiestates and principalities. Every municipality in the archipelago exists in a precarious balance of power and shifting alliances. Many states maintain large galley warfleets on constant alert, as they may be required to leap into battle at short notice in order to prevent an enemy from attacks on harbor facilities and cities. Wars flare quickly, are relatively common and fiercely fought, but usually of short duration and mostly confined to sea, culminating with (mostly unsuccessful) land actions against fortified settlements or scorched earth raids against rural landscapes. 

It’s very difficult for any one state in the inner archipelago to achieve a permanent advantage as they usually lack the land based military power to maintain an army in the field on an enemy island or to overcome the heavy fortification of their enemies. Supremacy at sea is usually the end goal and achievable however, as control of the sea lanes and all important trade routes is crucial to garnering the lion's share of the great wealth they generate. 


Inner Archipelago

Northern Reach

The Western Sea


Trade is extremely important to all major cities and states in the Thousand Isles. Sitting astride the seasonal east/west trade winds allow the Islanders to enjoy a privileged position connecting the trade of two continents (Mythras and Mbo) in addition to allowing them to easily move their own local goods to those markets. Trade has allowed some elements of society to become extremely wealthy. It is said in Haven Towne that there is no good produced anywhere in the world that cannot be had for a price. 

All is not perfect however. The trade routes to the Northwest have been blocked by the giants of Gianthome for many years and other seas beyond are rumored to have become even more hostile. Since the Goliath’s learned how to build longships two centuries ago, the The Northern Reach has become increasingly lawless, home to copious pirates that are growing in boldness. Since all easterly trade must route through the south and the lands of the Mbo, the merchants of the Isles chafe under foreign rules and tariffs. 

Trade to the south is brisk but tightly controlled and ruthlessly taxed. All foreign traders to Mbo are channeled through a single port (Bawaaba Mbo.) at the mouth of mighty Dorba River and foreign ships are denied entry to any other city in the continent, or sea routes to access to the western seas. As a result Bawaaba has grown to be the other great trade center of the region, rivaling Haven, and hosting traders from even further west, from fabled lands such as Bilad al-Sham, Mashriq and Jambu Dwipa. One of the dearest dreams of the merchants of the Thousand Isles is to reopen alternate routes to the west, bypassing Mbo and trading with those lands directly

Weather and The Trade Winds

The trade winds regularly sweep the Thousand Isles and are the key to the trading routes and strategies of the merchants. These winds blow reliably and quite strongly from Mythras to Mbo, one way in spring, the opposite in fall. They stretch north to south from approximately the northern tip of Etmarch to the coast of northern coast of Mbo

The Westerlies start in springtime generally around late march, and blow until May, taking the great eastern trade fleets to Mythras and Valoria

The Easterlies generally start blowing in late September and blow until November, and take the eastern trade fleets home again. Of course there is also a counter cycle of trade, western trade fleets that follows the winds to and from Mbo.

Generally in summer and winter there are no globally prevailing winds and the weather is more mercurial

The Isles are also home to great storms, like nothing Mythrans have experienced. NorWesters can occur anytime of the year from winter till early summer but are most severe when they coincide with an early trade wind in March. These are cold violent rainy storms, not as severe as Typhoons but still fierce and deadly.  

Around July the region enters Typhoon season which can last until October. These massive storms generally blow up from the southeast and sweep through the islands. The southern reaches are especially hard hit by these storms but they can wreak destruction all the way north to DragonHome. Typically the easterly trade fleet tries to return home after the Typhoons have blown out, catching the tail end of the Easterlies, but the timing of this is hard and it is not unheard of for an entire trade fleet to be lost to late and strong typhoon. 


The Thousand Isles are extremely advanced when it comes to Naval Warfare and far less advanced in land battles and sieges. The nature of the islands and the terrain make it difficult for opposing powers to field or transport large armies or conduct drawn out sieges. Also many of the interiors of the islands are wild and mountainous, ideal for guerilla warfare. Generally the wars are settled at sea, since most states are so reliant on sea trade, destroying their navy and embargoing their ports is generally sufficient to force a favorable settlement. This also plays well with the goals of most of the merchant houses that are often pulling the strings of the various rulers, they are generally less interested in territorial acquisition as they are dominance of the sea and trade lanes. 

The few times where the struggle cannot be settled at sea, the armies of the major states have struggled to achieve offensive goals. Several times in recent history inferior forces have been able to frustrate invasions of markedly superior forces via fortifications, defense in depth and guerrilla warfare tactics (Southward Isles, The Garden Isles, Invasion of Ende). At this point in history the major powers have become more or less convinced that such land actions are somewhat futile and the established land warfare doctrine is that no island can truly permanently conquer or subdue another via invasion unless allied with a native faction.  

The current naval doctrine of most islands favors large fleets of galleys. Haven especially is wedded to this, and has invested in a ridiculously large and powerful galley fleet. These fleets tend to be powerful short range strike forces, especially in the calm inner seas, and have the advantage of not being as influenced by vagrancies of wind. They are fast for short sprints and powerful in combat, especially compared to their relatively low cost. However they struggle in force projection outside of their preferred operating theatre, deepwater actions in the Reaches for instance or in the Etish Sea. They are also in danger of becoming anachronisms as the struggle to mount the larger cannon. 

To compensate for the disadvantages of galleys, Havan and most other states maintain relatively small deepwater fleets of light, fast pirate hunters and also utilize privateers and impressed merchantmen in times of war. The merchants on the other hand have trended toward larger and larger Galleons to fend off pirates by shere size, or lighter faster and heavily built Flyutes. Merchants also often travel in convoy  All these solutions are generally not sufficient to keep the pirates under control, so occasionally the major powers band together and launch a crusade on piracy to sweep the nests clean. These crusades are generally successful at suppressing piracy for a few years, but the pirates always come back.

The notable exception to the prevailing naval doctrine is Etmarch. Separated from the rest of the Inner Archipelago by the large and stormy Etish Sea, Etmarch has focused it’s naval strategy on dominating that body of water and thus preventing invasion. Thus Etmarch has the best deepwater navy in the Isles. The Etish Islands however are generally not much affected by piracy however and strategically needs to keep that navy close to home, so the fleet rarely sees action and doesn't really affect the piracy equation much.  It is interesting to note that when the Entmarch fleet was fully deployed against the Havenites ten years ago in the War of Antillian Succession, the deepwater ships acquitted themselves quite well even outside of their preferred operating theatre .


Pirates are a continual problem for the entire region. Most of the naval resources of the Inner Archipelago go into building and maintaining the large fleets of war galleys that dominate the inner archipelago or the great merchant fleets of Galleons and Fluytes that make up the yearly cycle of the great trade fleets. Deep water ships to hunt pirates are something of an afterthought for the merchant houses and governments. The galleys are useless in the open ocean of the Reaches and the merchant ships, while well able to protect each other in mass formations are too slow to catch the pirates. 

In addition the Giants to the north and Mbo to the south plus various rogue states among the Thousand Isles actively support the pirates as an effective counter to inner island expansionism into their respective spheres of influence. Local island governments and merchant houses also support individual pirates depending on the specifics of the areas affected.  The population and governments of the Reaches, long suffering under the heels of the great merchant houses, covertly and overtly support the buccaneers giving them a strong base of operations. .

Hence pirates rule the reaches and prey on the outlying islands and the inter island trade, even in the inner archipelago.


The Thousand Isles is primarily inspired by the 17th century Caribbean, economically, culturally, and historically. However 15tg century Venice inspired the governmental systems, especially of The Republic of Haven. The geography of the larger islands steals heavily from 17th century Indonesia in size and demographics, as the islands of The Inner Archipelago are considerably larger then their Caribbean counterparts. Yeah 


Haven Towne is the largest city in the The Thousand Isles, and capital of the The Republic of HavenLush, tropical and inviting, despite the best efforts of the inhabitants and industry of the town it still maintains a degree of island beauty. The bay is warm and reasonably clear, with craggy volcanic cliffs towering over white sandy beaches lined by palm, coconut and bamboo . Colorful birds abound, monkeys scamper over red tiled roofs, as a balmy  breeze bathes the island port. 

Far to the west, barely visible out of the tropical haze, great green volcanic cliffs rise, and far above looms the peak of the mighty volcano, Bynack Tor, that forms the backbone of this island. Far far away and yet so tall they it is still barely visible from the coast


Haven Towne occupies  a narrow peninsula into the wide bay Haven Bay. The Bay is almost entirely landlocked, only connecting to the sea via a narrow 1/4 mile wide channel called The Gullet Two rivers, River Bonny and River Sur empty into the Bay on either side of the Peninsula. 

The Bay is rimmed by steep cliffs to the south, and the headlands, but the northern part of the bay is much lower and can be swampy in places. 

Both the Sur and Bonny River valleys are wide, temperate and fertile volcanic valleys studded with small farming hamlets tilling the rich black volcanic soil, these valleys are the breadbasket of the metropolis

In addition to the barges of grain and produce that flow from the valleys into the city, the rivers also allow transport of goods arriving at Haven Towne into the interior of the island.

A system of aqueducts , originally created by the An, has been expanded to bring fresh water from these rivers into the city, to supplement the wells that dot the city.

About 30 miles up the Sur and 35 miles up the Bonny, the wide valley narrows and rises into a series of cataracts that mark the edge of civilization. Beyond this point, the foothills begin, the land  becomes steep, the valley  closes in, the jungle becomes dense and only small isolated mountain villages can be found. 


The climate and Weather of Haven Towne, as is typical of the Thousand Isles is characterized by a two-season year, tropical and uniform temperatures everywhere (except at high elevations), is relatively wet especially in the springtime, with high annual rainfall, high relative humidity.

The trade wind blows more or less along the length of the island from April  through June,and then again in the opposite direction from September through November.

The town is sheltered by the bulk of Bonny Isle from the spring westerlies and the associated storms , but the harbor is more exposed to the fall easterlies. Haven gets most of it's rainfall in the fall and winter and often has relatively dry springs and summers. 


Haven was founded over 600 years ago by the Annwyn Empire as a major Anchorage and fleet base. It marked the high water mark of their empire, their most remote outpost.

When the Annwyn empire issued The Recall, and withdrew their military forces, the small island town was left to its own devices. The vacuum left by the retreating An plunged the entire The Thousand Isles into chaos and anarchy for a century. Due to the leadership of Haven’s first ruling Governor Marcus Madrigal, the island not only survived this period but emerged as the leading mercantile and military power in the region. 



University District


Merchants Town

Governors District

The Armory

New Towne

The Castillo

The Gullet

Other Havon Bay Fortifications


River Sur

River Bonny


In addition to the same 17th century Caribbean inspiration of the overall The Thousand Isles, Haven specifically draws from old Havana and San Juan. Venice also inspired the governmental system. its history also has a dash of Umbar from Lord of the Rings 

Onlangs gewijzigd

Pirate Market - Entrance
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Pirate Market - Solstice Festival
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The Pirate Market
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Pirate Market - Auction House
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Pirate Market - Cathedralside
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The Drunken Mermaid
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Pirate Market - The Souk
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Tiny StrongArm
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Challenges of Might and Marksmanship
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Dungeons and Dragons and Pirates! What could possibly go better together? It's like peanut butter and chocolate right? Well, as scores of failed supplements have shown, it's actually a trickier mashup then you would think. While the spirit and style of the pirating in the age of sail is a natural and additive match to Dungeons and Dragons genre, there are a number of complications that can easily wreck or divert such a campaign. Unless you as a dungeon master are aware and proactive in your world building and scenario generation, you are likely to miss the mark of your expectations.

The purpose of the The Thousand Isles campaign setting is to create an historically accurate and internally consistent sandbox campaign setting compatible with dnd 5e for low fantasy age-of-sail pirate adventures. 

This campaign setting does not require any rule changes to 5e though I do Suggest some.

In a previous blog post I’ve talked about some of the issues with creating a good age of sail pirate experience under the dnd 5e settings, especially if you care about enabling player agency via internal consistency.

I’ve also described how I intended to solve or work around the these issues. I discussed key world building elements that foster the emergent thematic properties I want, then made specific suggestions around 5E game mechanics, specifically managing the magic system and ship combat.  

It’s probably a good idea to read those two blog posts and get an idea if what I am going for is what you are interested in. I did have a very specific theme and set of goals in mind while building this world, if your goals or philosophy differ too far from where I started, well that is totally fine, but this supplement may not work for you.  

This campaign world reflects those solutions. It is intended to be a “drop in” early 17th century region that can be easily incorporated into any 5e fantasy campaign works that features a sizable and relatively unexplored ocean with a focus on Tall Ships and Piracy. In this document, the excellent (and free) Dwarven Forge campaign world of Mythras is used as that starting point but it is relatively trivial to replace the few references to Mythras and Valoria with whatever fantasy campaign setting you are currently using.

All you need to do is give your characters a reason to get out of their own particular dodge and a ship to take them away and you are off! The HMS Lady Jezebel was designed expressly for this purpose and the city of Haven Towne or Skull River Bay would make good initial destinations. If you want an example of making that transition, check out the Hightower Bay chapter on the blog.

Finally this setting is an amateur home-brew setting released under the Open Game License. I have no intention of making any sort of profit off this setting, it’s entirely for fun. However this also means it’s a bit bare bones at the moment. While it does have a fair amount of detail put into certain areas it has virtually none in others. While I do plan to keep contributing to this setting it’ll likely never reach the completeness or polish of a commercial product. C’est la vie. The upside of this is those blank spots are entirely up to you as a DM to fill in. If you come up with something especially clever ping me over on my blog ( and maybe we can incorporate your contributions here! 

Hope you enjoy and happy pirating!

Guy Bayes