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When you get some friends take the opportunity to crew up for sailing and quests. You get higher rep and a bigger hare of the sinking loot if you are Captain. When a guild mate hooked me up with some of her friends who were high level I made a couple thousand coin on each voyage.
Batholomew Watkins' quests are easy cash and even if I sink my galleon, I still get to cash in on the quests and make a profit after repairing. If you frequently find yourself on Port Royal get the Sam Seabones quest. Sam hangs out near the shipwright and pays 25 gold for killing 2 skeletons. As I frequently find myself near the cemetery when teleporting in, and the jail is also close, I just take a few extra steps to kill 2 skels and go cash in with Sam. Josie McReady in the Royal Anchor bar in PR will also give you quests that pay well These get harder as your rep increases.
The PR Gypsy & Shipwright will give you quests, but these stop after a while, but Josie & Sam keep on givin'.
You can also try gambling to make some coin but of course that's risky. Some of your quests will require you to gamble so it's always nice to have some extra money in your account.
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