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This is a summary of techniques I had success with last year while fishing in the Bahamas. This is mostly for the sake of our friend Ben, who hopefully reads this post.

Rig:

I’ve tried rods+reels (admittedly, cheap ones).   I’ve had trouble losing fish when using a reel, so I prefer a different approach.

Starting on your end, at the back of the boat:  First, you want a length of thin but strong rope/line, about 1/8 inch or so.  You might want 50 foot of this.   Attached to this is 250lb clear mono, 20-30 foot in length.  Finally there’s a clip on the end of the monofilament to attach the lure to.   Ideally you have 2 swivels, one at each end of the mono.. and it’s better still if the swivels are the ball-bearing type.   This whole rig attaches to a cleat or other strong point on the transom of the boat.

This whole setup should be rated to 200+ lbs.  Be sure to get heavy swivels.  I’d also suggest buying some 2-barrel crimp sleeves that match the diameter of your mono.  These make very clean and strong loops at the end of the mono that attach to swivels and things.

Lures:

We had good luck with one of 3 lure setups.  As many things in life, the more complex and/or expensive systems do seem better:

1. (simplest)   Walmart sells 3 packs of these little squid skirts with a single hook/weight piece that’s reused.    Both the green/yellow and the pink/white ones are great investments.  Get lots of these.   We had very good luck with the pink/white setup.   They’re a great investment - for the ~4$ per 3-pack, I’d buy 10 of them before leaving.   Mostly pink/white, but a mix.
2. (balanced) A next step would be to buy fake ballyhoo lures.   I found some for ~15$ for a 3-pack of 8-9″ rubbery fishes.   With the ballyhoo, you want to add a skirt (above) that goes around the line, and falls directly over the front half of the ballyhoo fish.. a fish with a squid on its face looks strange, but it works.
3. (best)   Get frozen ballyhoo.   They’re sold either pre-rigged or not.  I’ve rigged them myself, but pre-rigged is a great convenience.   Do the same setup as #2 above, with the skirt around the nose of the fish.

Technique:

Drag as many lines as you like.   I’ve managed maybe as many as 7, but often do only 3 for simplicity.

Lures only need to be 25-50′ from the back of the boat.   When running multiple, I try to go for a wide coverage area versus a grouped/clustered setup.   You’re encouraged to experiment with placement.

Two things to try:

• Shock cords on the lines.   I have several lengths of bungee cord attached to the deck/hull rail on either side.  These try to dampen the fish pickup action.   It seems to be effective.   (the bungee is attached with a carabeener to a loop in the fish line.  The line remains cleated to the boat also.
• Slack in the line.    This technique is kind of hard to explain.    The idea here is to make a breakaway drag sort of system.   The rope is attached to a cleat, and then a 10 foot slack section of the line is achieved by using clothespins or other creative means.   The fish hits the lure and gets just a moment to swallow it.  A moment later, he trips the clothespin apparatus and the massive sailboat momentum slams the hook into the fish.

Miscellaneous:

Hooks quickly rust.  Have a sharpening stone or file to sharpen the hooks when needed.  Some go as far as to sharpen every use.

A gaff is very helpful to get the fish in the boat.   Hook and toss.

Location:   Deep water is good.   When I have my choice, I like to be in deep water, but only a few hundred feet from shallower water.  Fishing on the banks can be very productive, but you often don’t get to keep what you catch (because of fears of ciguatera poisoning)

Lures will pick up seaweed and other gunk that renders them ineffective.  Lines should be pulled in and inspected/cleaned as often as required.  I’d suggest cleaning each line at least every hour or so.