Beginning Your Pillage At Sea

First, check with your crew for policies about taking out a boat, what backup you need to take with you, which flags you are allowed to battle, etc.
Second, make sure you have enough time to run the pillage. Unlike jobbing or working on a boat you can't just leave in the middle of the pillage. To start with, for a short hop from one island to another in the same archipelago give yourself a full day from starting to prepare to go to sea to finishing up restocking the boat at the end of your pillage.
Finding a Boat to Use
Find out what your crew expects when borrowing a boat, or use your own.
It isn't a private boat someone would like left alone
You can commit to restocking it to the specified levels and returning it to its home port, even if your pillage does not go well
It isn't a badly damaged boat and has little or no water in the bilge.

Pre-Launch Checklist

Make sure you have permission to use the vessel in the manner you plan on using it.
Board the Vessel.
Inspect the hold.
Check number of cannonballs and rum. Buy cannonballs and rum if you're low. Ratio of cannonballs to bottles of rum should not fall below 1:1.
Tell your crew you are going pillaging and on what boat.
Before starting a pillage, it is reccommended to have at least 5 other swabbies besides yourself onboard. When a pirate becomes very skilled in swordfighting, then he/she may wish to do a "Solo" Pillage, though even for them it is smart to have a few swabbies aboard with them to assist in frays and battles.
Chart a course.
When you have a jobber come on to the ship greet them with a friendly "Ahoy!" or "Welcome aboard!" instead of a "station or plank" which would annoy or scare the jobber and would most likely make him leave the ship.

While at Sea
While you are at sea you will need to make sure that the pirates on your sloop are all contributing. Some pirates, including new pirates called “greenies”, will need more explanations and encouragement to do the jobs that need to be done. Experienced pirates, known as “seadogs”, often have extensive pillaging resumes and need little or no instruction.
There are a few ways to assign stations to pirates. Both in choosing which duty stations to fill and the manner of requests you will need to balance the needs of the whole boat, having a profitable pillage, against the needs of the individual pirates, to have fun and feel valuable and appreciated.
Ask for volunteers for a specific action, as in "Would one of you bilgers like to carpent?". Some pirates will volunteer for and enjoy duties that they would resent if requested or ordered.

Attacking: Rules of Thumb

When in doubt, attack.
Don’t attack:
When your boat is struggling or damaged.
When your guns aren’t loaded.

Ending the Pillage
If you lost the battle, or you have been pillaging a while, check the remaining shot and rum in the hold. If you are running low you need to plan to end your pillage.
After some length of time, when you are tired of pillaging, or you have lost so much of your crew that you don't care to go on, or your supplies are running low, you will need to end the pillage.
Depending on how urgently you want to stop pillaging, and if the bilge is low enough to support it, you may want to put extra emphasis on sails. You still need to be prepared for battle because you can be attacked again before you manage to port.

After the Pillage: Life back on Land
After extensive pillaging voyages, one may need to become re-accustomed to the ways of life on the mainland. The busy Pillaging lifestyle at sea often leaves little time for companionship of a man or woman, or whatever else a matey prefers. Getting back into the dating world can be tricky, manners and common courtesies are often forgotten during a bountiful pillage.Here are a number of fail-proof pickup lines to assist in the post-pillaging dating scene:

Avast, me proud beauty! Wanna know why me Roger is so Jolly?
Come on up and see me urchins.

I'd love to drop anchor in your lagoon.

Pardon me, but would ya mind if I fired me cannon through your porthole?

How'd you like to scrape the barnacles off of me rudder?

Ya know, darlin’, I’m 97 percent chum free.

Well blow me down?

Prepare to be boarded.