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The Wormwood Mutiny micromanages the timeline throughout the adventure, but as soon as Book 2 starts, the nature of the game changes completely. All of a sudden, the players are thrust into a potential sandbox. Even with a train conductor of a GM, the transition from day-to-day play is problematic.
My biggest concern is what to do concerning the pacing of the game? Do you play out some of the shipboard scenes between destinations? Do you skip right to the destination? I'm worried that the game will quickly become Adam Sandler's Click: The Musical RPG, with months passing by in seconds. But the other end of the spectrum is to continue to play out every single day, which was bad enough for the first twenty-one. In your game, what, exactly, happens after the captain says "Set sail for Port Peril/Quent/Tortuga!"?
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For the first couple of sessions, when having a ship was new and crew was scarce, I played 1 or 2 shipboard roleplaying situations. Something that required the new captain (and officers, since my PC's ran it by group consensus rather than dictatorship) to step up and make decisions.
Things like deserting crew members, murder between the opposing sides from the mutiny, gambling belowdecks (what, is that STILL illegal), the guard sleeping on duty, dissatisfaction with plunder divivde, potentially lethal disagrements between 'old hands' and newly pressganged sailors.
This served both to pace down the journeys, to give the players an opportinity to roleplay ship officers, and to set the mood for what kind of pirate vessel they wanted to run.
Later on, I had at the least one potential battle on each journey. That is, they sighted a ship, but could of course decide not to give chase.
Now, in AP 3, I'll let a week of journey pass without incident. Longer than that, and the crew starts to get restless, leading to various troubles (mainly roleplaying situations, only combat if the PC's escalate).
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There is a thread in here somewhere that deatils a very good Sandbox system for just this. I forget now what thread it is though, not much help I know sorry. The OP of the that post is a genius as its helped me now end. Maybe someone can remember the post? I think its s&s sandbox style?
I have divded the map up in to 50 mile squares (roughly 1 full day of travel)and let the players go where they want. I have tables, tables and more tables. Wandering monsters (from isles of the shackles as its better), shipboard events (from dead mans chest), hazards and ships (taken from all 6 books at the back.
Essenatily each day they can chose to, tarvel up to daily move rate, hunt a ship, re-supply, raid a settlement or head to a port. I then roll up for navigation and daily weather (dead mans chest) and roll twice for a random event (once day and night 33% chance and roll to see if ship, shipboard, monster or hazrad), thats pretty much it, it leaves the players to decided then and the GM to improvise. Depending on how the group likes to role-play its either just a sereis of dice rolls or leave it up to the players to do what they want each day ansd improve.
It all depends how much work you want to put in, I have a lever arch a4 binder (about 500 pages of stuff) just for the sandbox. But boy has it been worth it. Book 2 has taken me about 30-40 weeks of 3 hour sessions to finish, its been very enjoyable and the players even have their own tavern now in Senghor.
Using a day by day wind and conditions chart - which then dictate some overall rolls by the players for performance (or staying afloat). or even major decisions like keeping out of an area (say, whe a storm is brewing up). Or remaing in harbour (in a bay) for some more time.
Local conditions like reefs (perception checks)
At least two perception checks a day (and random hours), whether they spot anything afloat (basically one's random enounters).One roll for survival (weather forecasting)
Some set events for the social side : crew rivalry, ship breakage etc.
Also set "deadlines" for some encounters (which may seek them out ), plus actually running out of provisions.
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Once the party figured out sailing, the GM waived the checks by using the Take 10 rules allowing normal operations without checks. Storms would be different.
Once we were in control, we had daily checks:
Knowledge(Nature) for +/- chance for random encounters
Knowledge(Local) for +/- chance for ship encounters
Profession(Navigator) for accuracy of travel
Profession(Sailor) for speed of travel
I am not sure exactly if these were the specific checks, but you get the idea. Each day usually had several people make a few checks, and if nothing of note happened, took less than five minutes of play. Since no place has been more that two weeks travel, repeated daily checks went very fast, and took less than half an hour of game time.
At higher level, with sufficient ranks for the skills, you could even hand-wave the checks away if they want peaceful sailing. You still roll for the random encounters, but based on the favored method of travel. [For us, if in a hurry, we chose low random, high ship.]
/cevah