A monk will do fine in the shackles. I suggest the lawfulness of your monk be personal honor and discipline. There is a players guide so that will be helpful.
Think of how Bane acted in the last Batman movie. He would be LN/LE. Ra's Al Ghul would be LN/LE as well.
Your GM may introduce some variables... but generally speaking the PC's are going to be law-breakers.
Unless your GM changes the background a bit, you will *not* be government-sponsored-lawful privateers. You will be every-critter-for-themselves-chaotic pirates.
So if you wanna be a monk (not a bad choice considering that heavy armor + deep water = bad) you're going to have to find an in-character reason to stay with the rest of your probably chaotic compatriots.
And you will need a reason to have come to the sea to begin with.
Perhaps you are chasing someone who broke the law?
Perhaps you are chasing someone who harmed your family?
Perhaps a quest from your monastery?
Perhaps you have ideas about who should be running things on the high seas, and its not the current people?
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The Player's Guide is found here.
Your GM may introduce some variables... but generally speaking the PC's are going to be law-breakers.
Unless your GM changes the background a bit, you will *not* be government-sponsored-lawful privateers. You will be every-critter-for-themselves-chaotic pirates.
So if you wanna be a monk (not a bad choice considering that heavy armor + deep water = bad) you're going to have to find an in-character reason to stay with the rest of your probably chaotic compatriots.
And you will need a reason to have come to the sea to begin with.
Perhaps you are chasing someone who broke the law?
Perhaps you are chasing someone who harmed your family?
Perhaps a quest from your monastery?
Perhaps you have ideas about who should be running things on the high seas, and its not the current people?
I'm the one DM'g. Just thought I'd drop by. I will be making some minor changes here and there, but yes, the PC's will be lawbreakers. I'm not changing anything plot wise, just a few tweaks to the ship combats, and some npc's. Nothing major.
I'm very interested in the monk. The OP is very good at backstories and playing in both character and alignment.
I don't know how tied you are to the half-orc, but I believe there's an aasimar variant that allows for non-lawful monks?
As others mentioned, "law" can mean a personal code of honor - and strangely enough, some pirate captains instituted such codes. You can read about a few of them on Wikipedia. If you pick one of those as your 'law' then you should fit in among many pirate crews.
As an aside, we just abandoned a Skull and Shackles run because of a total party wipe in the first module (GM decided after our deaths that he'd prefer to run an original campaign instead of restarting the AP). A tip: A well-balanced party is very important for survival in S&S, probably moreso than any other AP I've run.
TWF ranger/ MoMS. Scimitar and unarmed strike, snake and crane style
20 pt buy
Str: 16
Dex: 16
Con: 12
Int: 10
Wis: 13
Cha: 10
1) rng- combat ref, dodge
2) rng- TWF
3) Monk- snake style, snake fang
4) rng-
5) Monk- crane style, crane wing
6) rng-
7) rng- imp TWF
8) rng- 2 weapon defense
9) rng- power attack
10) rng-
11) rng- 2 weapon rend
12) rng-
I am having a similar set of decision as we start a Skulls and Shackles campaign. Like you I am thinking of running a monk. I see little problem with the Lawful alignment since being lawful doesn't mean blinding following the law but having a strict code of conduct. Loyalty to friends and companions is a good place to start. Keep your word and try not to lie. Just be consistent in your actions. I am choosing Lawful Neutral because I think that is going to be easier than Lawful Good would be.
There's always the Monk archetype Martial Artist out of Ultimate Combat. They can be of any alignment whatsoever.