So I've been thinking more about seafaring skills and I think I have a better solution.  I recently got to browse through a copy of Dungeon Crawl Classics and I liked the skill system, so I'm using something similar for the Pirate game:
- Characters have an occupation from before choosing a life of adventuring
 - Tasks requiring a skill check have a DC between 0 and 20 depending on difficulty
 - Character with relevant Occupation roll 1d20
 - Characters without relevant Occupation roll 1d10
 - Roll is modified by ability score modifier where relevant
 - Blacksmith making a battle axe uses STR modifier
 - Blacksmith making a tiny key uses DEX modifier
 - Simple career tasks may not require a skill check for a trained character. If an untrained individual attempts these, the DM can decide on a case-by-case basis if a check is required. For example:
 - taking the helm of a ship for simple manoeuvres in fair weather- no check
 - managing the rigging for simple manoeuvres in fair weather- no check
 - firing a canon at a target- modify attack roll by DEX bonus if DEX was half of current value
 - If a character spends a long time doing a particular career action they may gain an additional career. The DM and players may negotiate this, but in general, it should be quite rare. For example:
 - If the ship's carpenter takes the helm on a regular basis for a year of game-time, he may add the Helmsman career
 - If the ship's carpenter is constantly having to treat other wounded characters in the absence of a Doctor, over the course of years, he still is probably not going to add a Doctor career without years of study. But maybe the DM will invent a Medic career which is more limited.
 - If you want an Occupation that doesn't appear here, invent it.
 
Occupations
Here are some occupations and some of the things they can do:- Seafaring Occupations- all know the basics and can serve as riggers, powder monkeys, lookouts, helmsmen in favourable conditions
 - Sailor- tie knots, fix sails, traverse rigging even in foul weather
 - as lookout, skill check to see underwater reefs
 - Helmsman- pilot a large ship or command an untrained person at helm
 - manoeuvre ship effectively in combat
 - skill check to traverse narrow passages through straits, reefs
 - Navigator- read/draw maps, get boat from point A to point B
 - skill check to go to particular hex(failure means ending-up travelling to an adjacent hex)
 - Ship Doctor- know how to set broken bones, install peglegs, care for wounded crew
 - skill check to double patient's healing rate
 - Ship Carpenter- fix boat parts
 - fix damage from canons, storms
 - Ship Gunner- fire a heavy gun and oversee it's maintainence
 - skill check to hit particular target
 - Ship Cook- create a meal out of nearly anything
 - Fisherman- catch fish
 - Marine- soldier stationed on ship
 - no penalty fighting on ship during high seas
 - Other Occupations(what are you, a landlubber?!)
 - Noble- member of noble class
 - begin with more starting funds
 - Smith- make simple things from metal
 - Gunsmith- make/fix guns
 - Leatherwork- make complex things from leather
 - Performer- entertain people
 - Professional Gambler- gamble
 - Pearl Diver- swim, hold breath
 
A Word on Character Class
- For Pirates in the line of Treasure Island you may only want to allow Fighting Man
 - in this case you may want to add a Burglar Occupation who makes skill checks when thief skills are needed
 - For more fantastical Pirate adventures like Adventures of Sindbad, you can just use standard DnD classes with the above occupations
 

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