Seafaring campaign advice

[Gwaednerth]

Hello, I have been working on creating a seafaring campaign for a one-on-one Pathfinder game. The setting is intended to be a swashbuckling/pirate movie style world with elements of noir film and horror. (The general feel will be very Pirates of the Caribbean, with gritty, cynical cities and horror worked into individual adventures)
A couple questions for the pros:
1) As I have never played/DMed a seafaring adventure, what are major things to look out for? Or is it basically the same as a land campaign?
2) Since this will be one-on-one what level should I start my player at? I definitely don't want to start them at level one, because that would limit encounters to, "You are attacked by a single kobold" Also, should I adjust the equipment she gets to account for not having a rounded out team? (I don't want to strand her with no healing if she plays a fighter, or wizard, or somesuch)
3) I've been working on the idea that the whole (terrible) social/economic/political system is being run by some sort of behind the scenes manipulator. What sort of creature do you think it should be? I was thinking maybe a lich, illithid, or water/swamp dwelling dragon. Or should I scratch this idea as it devalues the cynical overtones of the campaign?

Thank you!

[dascarletm]

1. Be careful on where you lie on the reality spectrum for shipfaring. Make sure you're where the player and you will be happy. Also bookkeeping, be it the cargo, ship upgrades, or crew. Make sure you are both on the same page for this. This has been my troubles in the past.

2. For me it depends on what position you want her to be aboard this vessel. Is she the captain? A lowly crew member? First Mate? I'd say you can make 1st level work (remember that their crew will be with them), but I'd go level 3 for a low officer position, and level 6 for captain. More important than adjusting the equipment is to adjust the encounters. Don't play up the character's weakness often. Perhaps crewmen can fill the gap in a minor fashion. Example: we found Blackbutt's buried treasure, it's most likely trapped. Luckilly I just added Joey "Quickfingers" O'Conner to the crew, he can open it. I'd even let the player roll for the NPCs. Maybe give them the benefits of leadership for free even.

3. Consider an advanced sea-hag like character, or... so it seems. The real culprit is a greedy human more vile than this creature ever could be.

[LTwerewolf]

The single player (and sometimes two player) campaign is the perfect place to allow leadership and minionmancy, since they're not really making anyone else wait. If they want to play some of the crew, go ahead and let them. Fewer NPCs you have to worry about, and lets them fill their own gaps how they want to.

[Gwaednerth]

Thanks for the suggestions. I think I might give her free leadership (or at least something similar), that's a good idea. I also like the sea hag idea, although they're a bit low CR, maybe a sea hag with druid levels. Thanks again.