Urban Renewal: Skullport

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Urban Renewal: Skullport

The Dungeon of the Mad Mage hardcover provides a pretty good amount of information about the subterranean city of Skullport. A subterranean city… the potential is immense. Unfortunately, the authors have crippled Skullport from the very beginning. Their idea of Skullport is basically a ghost town with a few shops and some flameskulls wandering the streets. Everything is very dilapidated and deserted, and that makes Skullport essentially useless for adventuring. It’s just a curiosity, and that’s really a shame, because the idea and concept have so much to offer. In this article, I’m going to put a new face on Skullport, in order to remake it into a place where adventures can take place. Not a happy place, or a safe place, but a place that feels real and alive. This article is really written for DM’s, but I’m keeping any spoilers out so that players can have a look and maybe pass some ideas along if their DM is interested in Skullport adventures. Let’s get started.

What Do We Need for a Living City?

If we’re going to bring Skullport to life, there are two basic types of elements that we need to provide for: there are elements that provide function, and elements that provide tone. Function elements are what we need to make the city work, and will be the sort of features that make the city plausible. Tone elements are the features that provide the qualitative feel that makes the city convincing. Without function and tone, we end up with Skullport as written in the hardcover: flat, uninteresting, and with no real reason to exist.

Function Elements: the How and Why of Existence

When we start talking about function elements, there are just a few main concerns that need to be addressed, because almost all of the elements that need to be developed in order to have a city that is worth having and worth visiting are going to be tone elements. You can think of function elements and tone elements like a painting. Function elements are the frame, the canvas, and even the paints themselves. In short, they are what you need for the painting to exist as a real object. Tone elements are the image being painted. Without them, you just have raw materials without a real reason to exist; without tone, function could just as easily be a pile of painting supplies that nobody has actually used to produce art.

And with that rather obnoxious and pompous introduction, let’s take a look at the function elements that we need to include in order to build our better Skullport.

Location and Layout

This is almost an easy one, because we’ve already been provided with maps of Skullport that provide almost everything we need to know about how the city looks as far as the physical structures that are in it. We have the general arrangements of buildings, and a pretty good explanation of the multi-level building plan, complete with separate maps for each of the three levels of the city.

We’ve also been given a general location of Skullport. It’s in an underground cavern, about on the plane of the third level down in Undermountain. It can be reached by traveling the Sargauth River, or through the Waterdeep sewers, or by teleportation circle. All of that is pretty solid material, but we can (and should) make a few additions and improvements.

When we start to talk about population and economics, it’s going to become pretty apparent that most of the people in Skullport (and there will indeed be people living in Skullport) are not going to be getting to the city through the incredibly dangerous dungeon of Undermountain. Likewise, mass movement through the single connection with the Waterdeep sewer system is not reasonable for more than two or three people every so often; secret entrances quickly become not so secret when there’s a procession of people and goods moving through all the time. Teleportation circles might be a good way to transport a small number of people, but they probably aren’t much use for commerce.

So, if we’re going to have a population, and the means of supporting that population, we’re going to need more ways to get into Skullport. Fortunately, we’ve already been given all we need by the hardcover. We just need to tweak a couple of things.

The first thing we can do to connect Skullport to the surface is to have a look at the map of the Skullport street level. If you look around the edges of the map, there are several passages out of the city, but the designers never really specified where they all go. For our purposes, let’s adjust things so that those passages lead up to the surface, either within Waterdeep or in the nearby wilderness. The routes will be dark and moderately dangerous, but people who want to get into or out of Skullport can hire a guide to help them safely use those passages. Some inhabitants might even be able to navigate the passages themselves. Finally, at least a few of these passages need to be large enough to accommodate pack animals or even carts, in order to facilitate the transfer of goods between Skullport and the surface; even though the Skullport in the hardcover has shops in it, it never really tells you how they’re getting their stock replenished.

The second adjustment to be made is to revive the machinery that was used to lift ships in and out of the harbor. The hardcover includes this as a feature, even talking about how there is (or was) a very hazardous route that a ship might take to reach Skullport from the ocean outside of Deepwater Harbor. However, in the hardcover, the machinery is no longer operable. We’re going to dispense with that, and make the ship lift a way for enterprising ship-captains (with the right experience and a skillful crew, of course) to use Skullport as an actual port. If you like Ghosts of Saltmarsh, by the way, this will give you a plausible way for the party to leave Undermountain and travel by sea to one of the Saltmarsh adventures.

However, we need to note that both of these methods of travel come with a cost. Guides to lead travelers through the underground passages are not going to work for free, and it’s entirely possible that some of them might rob and murder their customers with the alibi of a dangerous journey gone wrong. Likewise, the ship lift is controlled by whomever holds the fortress, and they’re certainly going to charge a substantial sum for using the lifts. Even so, opening up tunnel routes and repairing the ship lift will allow travel between Skullport and the above-ground world; the travel just might not be safe or cheap.

Economy and Trade

Let’s get one thing straight right off the bat: D&D doesn’t do economies in the strict sense. The finer points of economics just don’t translate well, and trying to create economic systems that are similar to those in the real world is mostly wasted effort; a village with some shops and shepherds that the characters might visit once or twice does not require detailed information about the price of producing wool based upon the weather last season, or how much the road taxes on transporting weapons will fluctuate based upon the political climate of the next kingdom over.

When I’m talking about economies in D&D, I have something specific and simple in mind. It breaks down into just three points, and they all have to do with the purchase and sale of individual items:

First, the availability of items for sale needs to be limited based on the location of sale. There will be a very limited market for fine art and antiquities in Skullport, because an underground cave city is just not that kind of place. However, it’ll probably be much easier to buy things like poison and holy symbols of evil deities in Skullport than in Waterdeep.

Second, the price of items must be adjusted based upon the location of sale. So, the harder it is to get goods in and out of a location, the higher the prices will be. Goods in Skullport will be significantly more expensive than identical goods in Waterdeep. It’s worth mentioning that convenience also comes at a cost, so Skullport shopkeepers can charge more for their wares because it’s so much easier to stop for supplies in Skullport as opposed to fighting all the way to the surface to shop in Waterdeep.

Third, there needs to be a clear way in which the items for sale will get into the hands of the shopkeepers. This is a big problem with the Skullport described in the hardcover: how are those shops getting restocked, anyway? We need a way for goods to move into (and out of) the city, and in sufficient volume to create a market for salable items.

And that’s all that I mean by economy. In short, you need to figure out what goods ought to be sold based on the location, decide how they’ll get into that location, and decide on a price for the goods based on the method of transportation (possibly adjusting for factors like convenience or legality). That goes for any location where characters can buy and sell things, incidentally, and it definitely applies to Skullport.

Now that we know what questions we need to answer, it gets quite simple. We already know how one gets into and out of Skullport: either through the tunnels, or using the sea caves and the ship lift. The other routes really don’t apply to this question, because they are either too small or too dangerous for trade. We know that transportation of goods is quite hazardous and expensive even though the tunnels and the sea caves, goods in Skullport are going to be significantly more expensive than the same goods in Waterdeep; I would say that half again as much as the item prices in the PHB is a good baseline. Items that are sought after by adventurers should be even more pricey because of convenience, such as lamp oil, rations, and the like; try doubling the PHB price for that sort of thing. Finally, some goods will be cheaper in Skullport, such as dangerous or illegal wares, or things that can be harvested in caves, such as edible Underdark fungi.

The last thing that you need to do is to increase the number of shops in Skullport, because the ones marked on the map are so few and so limited in stock as to be almost useless. My advice is to keep the shop names and the shopkeepers, because they’re full of good flavor, but to treat finding a shop more like it would be handled above ground in Waterdeep: if the party is looking for a shop that sells a particular item, and the item is something that can be bought in Skullport, just let them go to a shop that fits the bill. Searching, rolling checks, and traveling using the map is really unnecessary. If you want to make things really interesting, you might consider a random urban encounter along the way to the shop, and there’s a pretty decent d100 table somewhere in the DMG if you don’t want to make your own.

Tone Elements: Creating the Flavor of the City

Function elements are fairly simple, and also pretty cut-and-dried. Tone elements are much more interesting, especially because several of them seem like they should actually be considered as function elements. Nevertheless, everything we’re about to discuss is intended just to make Skullport feel like a real place, and to establish that it’s not a very nice place. Players need to get that vibe whenever they visit Skullport, and tone elements are how we do that. You can, of course, change any of these to fit your own vision of how Skullport should look, act, and feel. Still, make sure that you cover all of the bases, even if you prefer to change things and do them your way.


There are two main items to cover when describing Skullport’s population in order to create tone for the city. The easy one is population density, and the fun one is demographics. So, we’ll get the easy one out of the way first, and then get creative.

Population by Sneaking In Strangers

When I started out working on an improved Skullport, I decided that I needed to have a lot more people living and working there than in the hardcover version, and from that I decided that I needed at least a rough idea of how many people should live there. So, I carefully counted off the rough rectangular dimensions of Skullport using the ten-foot grid squares on the map, did a couple of multiplication problems, and came up with the rough area in square feet of the footprint of Skullport: about four hundred thousand square feet, give or take. I wanted to figure out a population for Skullport based on real-world cities, and all of those stats are given in square kilometers, so I had to suck up my foolish American pride and convert my Skullport number into 0.037 square kilometers (which I must say lacks the same poetic ring as the square feet). Then I looked up the population density, in persons per square kilometer, of the most densely populated cities on Earth, and I discovered that if Skullport was as densely packed as Manila in the Philippines (about 46,000 people per square kilometer), it would be home to about 1,700 people. Granted, that’s just using the lower level of Skullport, but even if the middle and upper levels were just as large (they’re smaller) and had the same area (they have less, because parts are just empty air), we’re still talking about a couple thousand people. We might be talking about less, because Manila is pretty packed.

I wasn’t terribly happy with that number to start with, because Skullport needs to be big enough that strangers don’t stick out much. If newcomers are easy to notice, there’s not a lot of opportunity for adventures there, because the player characters would be instantly obvious to the locals, and therefore under observation if not suspicion right away. But, trying to fit the number into something I’ve experienced in real life, I thought about my high school graduating class, which was about 700 people. All of those people were crowded onto the middle of our football field for commencement, so I’ve seen that many people in one place before. And I asked myself, if you had put three or four strangers into that group, would I have noticed? Probably not.

So, the population number comes out at about 1,500 to 2,000 people, enough to make sure that strangers aren’t noticed, which was the whole point. You can figure out your own population figures, or you can use mine, or you can just spitball a number without calculating anything. I only did the math because I’m writing an article and I want you to get the best idea value per pixel. Also I have fun with that sort of thing.

But, no matter how much fun we can have coming up with a number of residents for Skullport, that’s still the boring part. Now we get fun and creative.

Who Lives in Skullport?

This is the fun thing to consider, because your population number is useless if you don’t have any reason for the people who live in Skullport to be there in the first place. You have to consider why anyone would live in this terrible ramshackle city in a dangerous cave without any easy ways in or out. How did they arrive, what are they doing with their time, and why are they choosing to stay instead of running as hard as possible for air and light?

I decided that one of the largest demographics would be people who were persona non grata in Waterdeep due to prejudice or stigma. There are several D&D races who don’t mix well with the others, and it seems natural that they would try to find a place to live where there wouldn’t be a lot of “normal people” treating them poorly. So now I have a base population of drow, duergar, tieflings, deep gnomes, and even some half-orcs who have failed to adjust.

The next group into the mix is people who lived in Waterdeep but needed to disappear due to some kind of local trouble. This might include petty criminals trying to skip bail or otherwise evade justice, but most of them wouldn’t be guilty of serious crimes. I’m thinking theft, tax evasion, maybe even a little assault and battery, but not murder and arson. You can also add in some people who aren’t guilty of any crime, but have to evade justice anyway after being falsely accused. Pretty much everyone in this group would have descended into Skullport using the tunnels, and it’s possible that some of them would like to leave but can’t afford to pay a guide to lead them back to the surface. Maybe some of them are in debt to the Xanathar Guild or some other unsavory parties in Skullport, and it could definitely be harder to skip out on creditors who are willing to break your limbs. Anyway, at least some of these people are stuck in Skullport, and not happy about that.

We’ll also need to add some serious or professional criminals, and we can use the various factions from Dragon Heist to help fill in the blanks using pre-made organizations. The Xanathar Guild will dominate the organized crime element of Skullport, with smaller gangs either paying them tribute or trying to operate without attracting notice. The Zhentarim and Bregan D’aerthe should also be lurking around, and there should be at least a few Harper agents spying around on everyone. Aside from the faction members, there should be a smaller demographic of people guilty of serious crimes who are either on the run or have escaped prison. You can’t add too many of these, though, because putting too many chaotic-evil types into an area will facilitate a quick descent into blood and anarchy. Just a handful of really violent and depraved individuals will be sufficient to add a sharper criminal edge to Skullport.

Some types of business are illegal to conduct in the above-ground world, and Skullport provides a place where those activities can flourish. Add in a contingent of pirates who use the ship lift to find a safe harbor and a place to sell or trade their stolen goods, as well as some black-market merchants who deal in illicit goods like drugs or poisons. Slaves will also be sold in Skullport, coming either from foreign lands, or as pirate captives, or even abducted out from the mass of fugitives from Waterdeep. You’ll also find spellcasters who make their living by casting curses, raising zombies, and using coercive spells like geas. There will also be mercenaries looking for employers, and possibly some prostitutes and drug dealers, if you go in for that sort of thing in your campaigns. If you get a bad feeling when you include certain elements, just don’t put them in; making real people uncomfortable for the sake of having “realistic” features like human trafficking and drug addiction in your fantasy world is not worth it. Be edgy, but don’t be offensive. You know your group, and where to draw the line.

Last, we can sprinkle in some people who would be considered “monsters” according to the rulebooks, but who are intelligent beings with the capacity for social interaction. We’ll have goblins working as servants and beggars, hobgoblin mercenaries looking for work, bugbear enforcers for the Xanathars, and others of that sort. Again, not too many of these, because we need to avoid the city descending into absolute chaos due to too many really evil, lawless, or even feral types wandering around.

That’ll round out the population of Skullport. Remember that most of the people there will be fugitives and exiles, and many of them will actually be stuck in Skullport even though they’d like to leave. The violent criminals and “monsters” need to be kept to a minimum. When I think back to my population and the crowded streets, I think of most people trudging around, eyes down, with the stronger and more fearless types pushing their way through the crowd or being shied away from by the normal folk who have to share the city with them.

Law and Government

The easy way to figure out the problem of who is in charge in Skullport is just to go with what the hardcover says: the Xanathar Guild rules here with an iron fist, and that’s that. I decided to do something a little different with my version of Skullport, because I have a hard time imagining the leaders of a major criminal syndicate buckling down to the hard and tedious work of governing a town. I’m sure that you could just invent a sort of Xanathar bureaucrat NPC to run things, but I’m looking for a little more anarchy in this town.

Anarchy is actually out of the question as such, because if there is nothing to hold the strong in check and keep them from preying on the weak, then Skullport will devolve into… well, into anarchy. And we need something a little more stable than that. There has to be some reason to stop people in Skullport from doing whatever they want, but I don’t want to have “law enforcement” types wandering around the place. Skullport does not need a City Watch like a respectable aboveground settlement would have. I’m thinking of something more insidious.

My version of Skullport is ruled by fear. And I don’t mean that there’s a governing individual or organization that maintains its rule by making people afraid. I’m talking about people’s fears being the thing that keep their behavior in check. In Skullport, you are allowed to do anything you want to anyone you like as long as you can get away with it. The question becomes, “can I get away with doing Awful-Thing-X to Person Y?” And that question is what drives the fear that keeps everyone’s eyes down.

The problem with any particular person as a target for crime and violence is the uncertainty as to what might happen to someone who tries to victimize that person. Maybe that vulnerable-looking little halfling is going to shove a fireball spell down your throat when you try to rob her. Maybe the downtrodden street sweeper has connections to a gang that will come and beat you half to death if you try to beat him half to death. And just about anyone could take out a hit on anyone else in Skullport: plenty of muscle for hire, if you have something that needs muscle.

And, of course, the ever-present Xanathar Guild brutes wandering around keep out-and-out riots from developing, because riots are bad for business and riot-inciters are easy enough to kill if you’re protected by the biggest gang in town. They’re not law enforcement in the traditional sense, but they do provide for a certain amount of order in the streets.

Could this actually work in the real world? Probably not, but D&D isn’t the real world, and in my opinion (and it’s a good one) it really shouldn’t try too hard to be. The idea of a lawless town that’s kept in some state of order because people are afraid of each other is interesting at least, and it’s also good tone for Skullport. Those crowded streets of dejected people trudging through with their eyes on their shoes are kept that way because everyone is kept in line by the fear of their neighbors, and not because there are official police types keeping an eye on things.

Skullport is a place where people go to disappear from the aboveground law, from creditors, from society. It’s a place sustained by commerce based on piracy and slavery, where everything has a price tag for those willing and able to pay. If there’s to be any law at all, it needs to be a law of violence, with swift and brutal retribution for wrongs done, and the notion that the citizens arrange for their own retribution is just about right for this kind of town. If you don’t know how dangerous anyone else truly might be, you play it safe and leave everyone alone… and if you don’t, there’s always the Xanathar Guild to crush anyone who causes a disturbance that’s bad for business.

A Conclusion

So that’s Skullport, in the broad strokes at least. We’ve gone from a ghost town to a town with people in it, and they are miserable outcasts, and they are criminals, and they are mostly trapped by society and poverty into eking out whatever kind of life they can in an underground cavern where everyone minds their own business and keeps their heads down.

Skullport survives on the kind of trade that flourishes in places where there’s nobody willing to keep it under control. The wealth that flows through the town comes through piracy and slavery: stolen goods and stolen people. It’s quite literally the underbelly of Waterdeep, where the laws and customs that keep a city civilized don’t apply deep down, deeper even than the city’s back alleys and sewers.

The idea of an underground settlement is a brilliant one, even if it isn’t breathtakingly innovative, and the designers of the hardcover’s version of Skullport have already provided the concept, along with maps and locations and some colorful characters to run the shops. Where they went wrong was stopping at that, and leaving the place unpopulated and unused. All of the potential of the place was wasted when the sea traffic was cut off and the streets emptied.

But that’s all right, because Skullport only needs a few changes to become a living place. Not a vibrant place, but a gritty one, and a good counterpoint to the high civilization and culture of Waterdeep. It’s a place that has huge opportunities for adventure, or at least for being a convenient but unpleasant rest stop for those delving into Undermountain. Adjust it, and use it… waste not, want not.

3 Responses

  1. Paul Mitchell says:

    A great post on an area that definitely needs to be included in any Waterdhavian adventure.

    A note on economy. The Skullport economy is directly tied into dungeon ecology: the inhabitants at the very least need to be fed. Where does that food come from? If the locks are closed, it has to come from underground. The Twisted Caverns and Wyllowood are both potential “farm” levels. Trade between these levels and Skullport can be facilitated by river transport. The war between the Kuo Toa and the Aboleth in the Twisted Caverns interrupts trade, adding to the suffering of the settlement. If the Arch Druid Wyllow is removed, that level might be exploited by Duergar, Drow or the Xanathar Guild for its resources.

    Xanathar interest in Skullport is also economic in its logic. It is a secure base through which they can manage the slave and drug trade. Limiting trade with the surface allows them to control the economic fortunes of the settlement, which also controls any potential independent threats to their authority developing amongst the Skulkers. House Auvryndar’s interest is more in terms of the geographic access Skullport facilitates with regards to its goal of undermining (literally) Waterdeep, however. Azrok’s League is simply in the way of those ambitions. The Hobgoblin settlement is key as a source of muscle for the Guild, and explains the mindflayer’s presence there.

    Last, this is clearly a complex and adaptive system: players will (mostly) want to eliminate the Xanathar Guild. But is that the best thing for Skullport? The Guild does provide some order in an anarchical space. Eliminating them causes all the other factions to reach for the control levers. The settlement’s society could oscillate significantly if the Guild is eliminated – there would be a rump of loose Guild agents plus Harpers, Protectors of the Song, and Zhents that all would get involved. Some older factions might re-emerge. Townsfolk themselves might be angry with the group of adventurers for making things worse.

    There are a set of resources that are useful to complement the DoTMM Skullport description. The published DoTMM adventure, for me, represents what ultimately happens if the Guild retains control of the settlement. Joseph C. Wolf’s 2e Forgotten Realms supplement “Skullport” represents the settlement at the height of its development – pre Xanathar Guild, and maybe where it could be again. It has a very detailed list of businesses, NPCs, and factions ( https://docplayer.net/30187290-Skullport-joseph-wolf.html ). The 5e “Shadow of Waterdeep” adventure on the DM’s Guild ( https://www.dmsguild.com/product/308753/Skullport-Shadow-of-Waterdeep ) is an intervening scenario between the impoverished DoTMM version and the riches of Wolf’s version. That set gets at where this post aims for: the Xanathar are in control, and the settlement is in economic freefall, but it still retains some of its former social vitality. It gives enough hooks for the PCs to care about what is going on and some ideas on how it might be solved and lots of detail for the DM to work with.

    • There are definitely a lot of good tie-ins possible between Skullport and the surrounding areas, and I’m always in support of changing published modules to fit your own needs. My version presented here is designed more as a stand-alone venue, intended to provide a city environment that is in stark contrast to Waterdeep, as opposed to another “level” of Undermountain as you’re suggesting. The issue of economy is similar: if Skullport is essentially another part of Undermountain, feeding the population is an issue. With the stand-alone version in this article, it’s better (or at least much easier) to just establish that Skullport has trade with the surface and the Underdark, that food is part of that trade, and leave it at that.

      • Paul Mitchell says:

        Its an excellent counterpoint to Waterdeep; an underground Bizarro-world. It certainly doesn’t need to tie into DoTMM – all that could be assumed in the way that Goblins always find a way back into a dungeon even if the players have cleaned out and controlled all the access points. I found that understanding the economic factors within the settlement really helps sort out the motivations for the various factions. Why would the Xanathar shut down the locks (other than they’re a bunch of jerks)? If they were absent, how would the factions behave in terms of seizing power?

        Great post, keep up the good work!

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