3.5 Pirate Game (suggestions welcome)

[Ben Powers]

I'm running a pirate game, where the setting is a barbados-style large expanse of ocean dotted with thousands of islands of various size.
It's thus far been a "very little prep" thing, but the vibe that's emerging is something of a golden age of piracy meets Homer thing. Like the Odyssey but with Anne Bonney and Mary Read in the title role. It's also my first gestalt game.
My knowledge of piracy is pretty good, eg the pirate republic at Nassau and the infamous Tortuga have been combined into a fantasy equivalent, the imaginatively named Tetsudo.
My knowledge of bronze age literature is a little less well rounded; I can tell you Cyclops, Scylla & Charybdis and Circe and the isle of pigs before I come up short.
The characters are Annabella Roxx (rogue//ranger), Bertha Bluntz (swashbuckler//wizard) and "Hung" Herbert (druid//barbarian). They are at best neutral (recently defeated a slaver and had a brief discussion about selling the slaves before deciding that was one step too far and releasing/recruiting them). They are already on a larger quest arc involving an old treasure map and the Unseelie Court, but I'm looking for various ideas for stuff they may come across on islands. You can rip it directly from the Odyssey or the Argonautica if you want because honestly, I won't be able to tell.
If anyone thinks of anything which would be cool to gracefully insert or shoehorn in, holla at me yo.

[Ephemeral_Being]

Make sure you have a plot, and the campaign isn't just raiding ships. Because ships in DnD are so expensive, you never WANT to hit them. You want to board the enemy vessel, and commandeer it. And that's fine. Once. Maybe twice. But the third time, your party is sick of doing the same thing over and over again. There needs to be a REASON for them to be pirates. As great as the premise of Firefly sounds, "Find a ship, find a crew, keep sailing" becomes a heck of a lot easier when your ship doesn't require fuel and you can pay your crew less than a gold-piece a day each. Meaning you can crew your entire ship for nearly a month for the price of a single magic weapon.

The encounter tables in Stormwrack are abysmally low. It's 4% an hour. You get (on average) an encounter every four days. Sailing from Waterdeep to the Moonshae Isles or Neverwinter takes much less than that. I had been running a Pirate campaign for five sessions. We quit last night, because NOTHING HAPPENED. The average ship (caravel) is meant to be crewed by a bunch of first-level NPCs. They have maybe one Wizard aboard, and a couple of seasoned navigators. But still, level 3-4 tops. If you start your party around level 7 (which I did to justify their owning a ship), every battle is just laughing at how bad the NPCs are.

Now, granted. Part of that was my fault. I could have changed things up. Increased the random encounter rate. Crew the ships with tougher enemies. Actually put a plot into the campaign (though in my defense, I was asked not to). But if you strictly follow the rules in Stormwrack, then it gets really, REALLY boring. In five sessions, I don't think a single person even took damage. It was horrible.

So, to sum up, increase the encounter rate, have a plot BEYOND "I wanna be a Pirate," and don't make encounters that are correct by the book but entirely pointless for the party.