I'd always been hesitant to use fresh pineapple in my drinks because of the expense of sliced pineapple at the grocery store -- a small package of chunks can run up to $5.00 in my area. I'd attempted to cut up a whole pineapple a couple of times with just a sharp knife: it worked OK, but after a good 15 minutes of effort I ended up with something that looked more like a science experiment than a garnish.
Recently, I came across a William & Sonoma-branded version of the Vacu Vin pineapple slicer in the clearance rack of their otherwise highbrow store. It's deceptively easy to use: you slice off the top of the pineapple, then push the Vacu Vin down into the flesh of the open pineapple, twisting as you move deeper into it. When you get to the bottom, you pull the device up and out of the fruit and you end up with a length of 1/8" high, perfectly spiraled pineapple.
Cutting the pineapple this way takes less than a minute, the fruit is ready to cut into rings or smaller slices, and you end up with a hollowed out pineapple -- perfect for pouring drinks into!
There's three models available: a plastic version with cutting wheels for three different sized pineapples, in plastic at a single-sized, and in stainless steel at single-size. My single-size plastic has been doing great -- the stainless steel model would be a good choice if you cut a lot of pineapples, but is probably overkill for the average person.
$7.95 – $18.95