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Building the Old School Sandbox Campaign in Roll20

Greetings Dungeon Master!  My name is Ed Kann and I am a long time veteran DM with roots going back into the ancient mists of 1978.  Besides writing and running my own homebrew campaign I occasionally do spot illustrations and cartography for OSR game books.  I am here to start a thread dedicated to my keen interest in building a classic style sandbox campaign specifically designed for the Roll20 environment.  In this thread I'll talk about my experiments with different approaches to making maps, customizing homebrew elements so they fit with the look and feel of the Roll20 application and discuss my own approach to this question of letting the players enjoy the feeling of a wide open campaign world where almost anything is possible. First things first.  The question immediately arises as to how well developed and "pretty" do you want your campaign in the Roll20 environment versus being able to fly by the seat of your pants.  I decided to go with a set campaign region rather than opening up a wide open world.  In my experience low level characters in particular are usually happy to explore a starting city, surrounding villages, dungeons and several wilderness areas all within about a thirty to sixty mile radius of their point of origin.  Only a very few times in the thirty plus years that I have DM'd have I had groups start and immediately board a ship to sail elsewhere.  I've certainly been able to wing those games with no problem but for my Roll20 campaign I wanted finished and detailed maps not only of city areas, dungeons but also of specific wilderness and encounter areas, all of these finished along with portraits of NPC's, monsters, well populated and finished dungeons etc... To my mind players in a fairly wide open but geographically limited region can still communicate that sandbox feeling without being anything like a railroading adventure path style.  I have no problem with adventure paths.  I've run games with that approach as well but I just prefer to invest the time and energy to do something in the more complete sandbox approach. The campaign takes place in the SW corner of my larger world map on a jungle covered tropical island just off the Eastern coast of the great Emirate of Sakalan.  It is called the Isle of Wairoa and is the three hex island to the immediate East of the big island of the Emirate.  The Isle itself covers a geographic area approximately sixty miles North to South and approximately fifty miles at its broadest point West to East for a total of roughly three hundred square adventuring miles.  More than sufficient land for the current sandbox campaign.  In addition to this the campaign region includes the potential for sea going adventures on the Sea of Harlots in the immediate area and to a smaller one hex Isle to the immediate NE of the Isle of Wairoa. Storms, encounters and sheer bad luck will keep bringing the characters back to the Isle of Wairoa during the span of the initial campaign.  This particular project has a build schedule from August - September for the Beta and initial maps and then an ongoing build cycle through the end of December 2013 when everything will be finished.  Characters will be able to continue to adventure in the Isle of Wairoa sandbox after that but I will then begin an initial build for a second sandbox across the sea to a much different, Northern environment.  The grand goal then is to open this second environment / sandbox by March of 2014 so that players will have two very detailed regions to adventures about in. All this puts me in mind to how fantasy MMORPG games need to be built with their various zones and links which define which paths can take a character from one zone to the next.  To keep it all straight I had to consider how many zone maps I wanted to build and how they might all be described in relation to each other. This is my initial rough draft map for the various zones in the Isle of Wairoa sandbox.  The city of Jamorka is a large chaotic sprawl of shacks and shanty style buildings built by the Corsairs and which functioned as the capital of their pirate and slave taking operations for more than a century.  About five years ago the Church of Tyrean managed to seize control of the city and now attempts to maintain control.  The Bishop Godfrey of Giles is the church high official acting as governor of this Tyrenean colony. The city itself is broken into nine zone maps.  Three along the water front and six more inland.  I describe these maps as locations at the center (mostly) of the more well policed and secure sections where the Bishop and church have been building larger buildings, respectable Inn's, stone shops and the like surrounded still by the squaller of the old Corsair capital.  Important campaign locations are scattered throughout the nine maps along with resources for the players, useful people to know, guilds, locations for hiring mercenaries when necessary, scribes or getting items identified, places to break into should the players decide to roll with a more thief oriented campaign and many entrances into the sewers, old sea cave tunnels and an underground city built beneath the streets of Jamorka called Undertow.   Whenever characters "zone" from one city map to another they face a random encounter roll.  These encounters occur out "in the sprawl or narrows" of the old Corsair city where the Bishop's law is difficult to enforce.  Should the characters roll an encounter I am building smaller, appropriate encounter maps where these fights take place.   I have a time keeping method for tracking the course of time in the campaign that ties into movement between zones, the passage of a combat and so forth that hopefully is forward thinking and works well in the Roll20 setting.  I want players to feel the sense of time passing and the use of supplies and resources in what usually accounts for a shorter individual game session of between two and three and a half hours.  This requires some changes away from the traditional table top methods and approaches for tracking time. That's about it for this first installment.  More to come. 
Screenshots, Character Portraits, Price Lists - The Handouts Function There are dozens of beautifully rendered fantasy video games available each with a great many zones.  The screen shot above is from the Age of Conan - Jungle port of Tortage.  Locations like Tortage are a source of inspiration for the look and feel I want to have in my own sprawling former pirate enclave of Jamorka and so images like this make for great show and tells for the players. You can use the GM function to input additional information depending upon the screen shot you use.  You can use gimp or photoshop to size the image so it is made for computer viewing only so that you are not using up very much space in your account. There are NPC characters likely to be enemies for the players to fight.  These you can set up both as characters with their own portraits, character sheets and tokens and you can also use the handouts function to share a character portrait, especially if you are having to roleplay that character as the DM.  Players can take a look at who or what they are talking to in the encounter with a spiffy portrait. For my own campaign price lists for shops is another tool that I can use to build the environment.  Eventually I plan to have most of the shops built as interior locations with their own maps but at least initially I can set up the price lists of what each shop carries and their prices.  I can use photoshop or gimp to place a character portrait for the shop owner in the upper corner and then fill the rest with a spiffy price list with a nice parchment background for atmosphere.  Players enter a shop and I can RP...yes, sires, what can I do for you this misty day?  Pop up comes the price list for that shop.  I don't have to sit there reading it to the players.  Everyone can eyeball exactly what is available and the asked for price then decide if they are interested in any of it.  This should speed the process of purchasing items and supplies.  I also have a list of asking prices for several dozens services in town as well as a price list for spell support from the major Church and lesser temples in the city and magical support from the Pentagarchy / mage faction in town. Jamorka is on an island where difficult seas, monsters and pirates make imports perilous and expensive.  Prices for many metal crafted items made beyond the island are twice the listed price.  There are plenty of items you simply cannot purchase and others that are quite common.  Taking the time out to stock the shops in your city communicates to your players something about the environment surrounding them.  Fear not, you do not have to initially stock every shop.  I plan to eventually do this but for now I have price lists for two armor shops, two weapons shops, three adventure supply shops and then a couple of random shops I believe characters might wander into at lower levels.  These price lists are generic and I don't need to assign them until the players actually take the time to walk into a shop in game to have a look around.  When I create the handouts for these I don't assign any shop name to the handout or have any shop name appear on the handout.  That way I can use it for whichever shop I need a price list / handout for at the time.  Eventually these will all be assigned and every shop in the city and surrounding couple of villages will have a specific NPC owner with their own little plot lines and hooks and their own particular inventory or services.  That is a fairly large task taking at least a couple of days in hours to accomplish and will get knocked out in pieces while the rest of the building of maps and so forth is underway.
Good stuff! Love the hex map - is that from Hexographer?
Campaign Map - Grand Scale Yes.  I spent quite a bit of time on my grand scale campaign map / world map.  I rendered several versions over the years by hand, a close version to the final in Hexographer and then this final version in Hexographer.  I've been working on the campaign for a long time but this final map probably took me a good ten hours of work to complete.  If the image doesn't show up you can follow the link and save the map to your machine.  This full version is a JPG with good enough resolution that you can zoom in at 100 percent view and get a good look at regions, names, roads and all the little details.
Time and Time Keeping In speaking with Simon, our earliest regular player for the Beta it occurred to me that some sort of codified time keeping system beyond the one turn equals ten minutes presented in the rules might be helpful. Especially when running in a computer environment and for play sessions lasting three hours versus the eight hour marathons of days gone by I think it is wise to have some means to mark the forward march of time in this sort of game. Some thought to supplies, the renewal of magical spells and the using up of daylight in some instances is an important part of the “feel” of old school table top RPG's. My campaign works to bring back to life some of the feeling of those old classic campaigns but in the modern environment of a virtual table with players from New York, Boston, Chicago, Kansas, Scotland, the UK and Germany. Skyrim is a favorite fantasy RPG played strictly on the computer. In games like Skyrim a day passes in an hour of real time and nobody gives this much thought. In table top style games players are more concerned with realism. They want things to make sense to a certain degree and suspension of disbelief can sometimes be a little harder to obtain. I hope to strike a balance between these two issues of needing a means to have time tick past quickly so that the management of supplies, spells and daylight becomes an active issue at the virtual table and keeping it all at least somewhat within the realm of believability with the system outlined below. The Ahk'aton. Each cycle of day and night in the Kingdoms Chimerical is divided into forty eight periods called Ahk'atons. The word Ahk'aton translates into an old Rakian word for sand footprint or literally the paw print of a creature left in the sand. The day and night cycle on the World of Kingdom's Chimerical is not the twenty four hour period we experience on planet Earth. Likely it is slightly shorter but the exact time I choose not to reveal in specific terms. If you want to know the answer to that secret you will have to travel to the Hundred Kingdoms of Man to discover this for yourself. The day and night cycle of forty eight Ahk'atons is divided further into eight Ma'hats or beasts each Ma'hat being comprised of six Ahk'atons. In any cycle at least three Ma'hat make up the period of night. It is an easy affair therefore to divide night watches into three periods, assigning each watch to a party member by its name. Every Ma'hat is named for the beast it represents. The three Ma'hat of the night Ahk'atons are (in order of earliest to latest) tiger, vulture and snake. One Ma'hat straddles the morning hours which slip between early morning and darkness depending upon the time of the year. This Ma'hat is dragon. Dragon is not usually included as a watch in adventuring parties for it is the time when groups rouse themselves, eat and prepare spells for the coming day. Four Ma'hat's are therefore left to make up the period of daylight. These are (in order) hawk, horse, mule and dog. The Ahk'aton and play. A typical turn exploring a dungeon, zone of wilderness or city zone uses up one third of an Ahk'aton. Combats in the game are considered to involve not only the period of surprise and combat but also the period of healing, picking over the slain for loot and generally getting the party ready to move forward again. Any combat however long or brief in combat rounds uses (for my purposes) one Ahk'aton. Travel between Zones There are close to fifty map areas (zones) not to mention side zones and dungeon maps in this campaign. Travel times between connected zones are already defined by the DM. In general it takes between 2 Ahk'atons and 5 Ahk'atons to move between zones. It should be noted that every time characters transit between zone maps there is an automatic roll for an encounter. Encounters are usually bad for the party. They usually are played out on their own pregenerated / smaller encounter maps and are considered to happen in the DM defined terrain between the zones. Rations and Play A standard wine or water skin carries three uses of liquid. A standard bundle of rations or food item (a roast chicken) has two uses. Rations are scheduled to be consumed three times between the Ma'hat of Dragon and Dog and at least once of these three during the Ma'hat of Dragon. Skipping any use of water or food allows the DM to penalize one of your character's d6 skills making it function at a permanent disadvantage until the situation is corrected.
Making The Maps and Zones In a sandbox table top campaign players can go absolutely anywhere.  This is all well and good but that makes having maps for lots of the fun areas a little tough.  In my limited sandbox campaign I am working to create these sorts of battle map style bottom layers for my maps where most of the main bits are created and then use the library tool to drop in doors, furniture, tokens for NPC's or monsters and all of the rest of it.  I like this approach because it gives me this sort of simple under map I can carry on my laptop or in a binder to reference while writing places up or expanding upon existing write ups.
This is a master map for the various zones that have corresponding "live" Roll20 maps for exploration and game play.  In the context of the campaign these are considered to be well patrolled and "relatively safe" sections of Jamorka where the occupation forces have things more or less under control.  Players must cross regions of the city which are not well patrolled or are completely left to the forces of the Corsair warlords which still occupy parts of the city.  Movement from one map to another uses between 2 to 5 units of time and requires an encounter roll.  An encounter moves the players to a smaller encounter (battle) map where whatever encounter or skirmish has been set up in advance and is ready to be played out.  These side maps reflect the extremely narrow and twisting alleys with choke points and dead ends which make much of the old city sprawl between the more refined main districts. The connected districts on the West side of the map represent the "Fortress" which stands on a commanding hill looming over the more squallid Jamorka sprawl.  The Fortress is made up of a three level Abbey, the Great Chapel and outer ward, barracks area as well as a multi map and multi level palace, the current home of Bishop Godfrey of GIles, the Church appointed governor of the island.
The Idea of copying the zones principle from MMOs for a roll20 sandbox is smart. Looking forward to your progress.
Hey fellow Traveller. Referee since '77. I have started a bit of this for sci fi here. getting up to speed. Realize your players want to make sweet love to you but you live too far. I eat up games like this but can hardly ever find a DM willing to go the 100 miles so i shoot for the goal myself. Good stuff great stuff. I use screenshots from my Neverwinter nights to do pics for taverns and stuff. EVE online character portraits for Traveller NPCs and screenies. I am lucky to have wonderful players here. i hope they never find your games, because i know those are like a player has to die to get an open spot. hoo yah. Luck.