We have long been fans of the Southside cocktail, not that we always think to make it. It's one of those great summer drinks we like to make for guests (and taste what's leftover in the shaker) to help us remember how delicious it is. So, when Kelly Sanders over at House Spirits posted a grilled pineapple version on the Aviation Gin Blog—well, what could we do but fire up the grill!

First, let us say that if you are new to the Southside, or you simply haven't had one in a while, do yourself a huge favor and follow the link above and make that drink right now. It's simple and delicious, and although it does require some mint, you'll be happy you went through the minor trouble of getting some. Actually, why aren't you growing your own mint? Did we forget to remind you to have a Julep on Derby Day? In any case, growing plain old spearmint in a pot on your deck like we do (or in a garden if you happen to have a green thumb) is one of the easiest improvements you can make to your home cocktail program. Mint appears in so many wonderful concoctions that it's worth the tiny challenge of getting some planted. Once you do, it really takes off and by the end of the season you'll be cutting it back for next spring. Anyway, the original Southside is a fantastic way to enjoy a refreshing gin cocktail all summer long.

Now that we got that out of the way let's talk pineapple. You really need to get a fresh pineapple for this. If you have a choice, look for one with a yellow exterior rather than green. The green ones are more durable during shipping, but they are not ripe, and since pineapples stop ripening once picked, you will be happier with one that isn't as green. The best way to cut a pineapple is to start on the sides with a huge, sharp knife. Stand the pineapple upright on a cutting board grabbing the leaves in one hand and carefully slice off the rough exterior with downward strokes, rotating as you go. You will notice that once you get into the sweet flesh, you end up leaving sharp brown spines all over the surface. These are like deep round pores with tiny thorns inside. You can cut them off with deeper downward cuts like removing the skin, but when you do, you take off a lot of edible flesh in the process. We like to use a spiral cutting technique for the spines after we take off the skin. Not only does this neatly remove them, but it preserves the flesh in-between and looks absolutely beautiful. This also allows you to appreciate a bit of natural geometry!

To remove the spines, first cut off the skin as explained leaving only the brown embedded spots. It can help to round off the top and bottom edges. Next, cut off the bottom but keep the top leaves for something to hang onto with your other hand. Now, observe the spiral lines as they curve down from the leaves to the base. Take your knife and cut a shallow wedge shape along this spiral line from the bottom to the top, first along the top edge and then back along the same line on the bottom of each spine. By cutting a v-shape around the fruit, the spines fall right off and you keep a large amount of flesh between them. It sounds a little confusing and the picture helps, but once you get the hang of it, you can easily remove the spines in gorgeous arcs around the fruit. This can make an impressive centerpiece as-is, but don't lose site of our goal!

To complete the carving of the fruit, slice off the leafy top which has served as a natural handle until now. Finally, cut the pineapple from the top to the bottom through the core. Do this three or four times like cutting a tall pizza into wedges. Be careful—it's slippery! We find it easiest to do three cross-sectional cuts through the middle leaving the pineapple standing vertical the whole time. This leaves you with six tall wedges. Take each wedge and cut off the the core vertically. Whew! You are done. Set aside the triangular core sections and use them to infuse Campari and Luxardo to make the Riviera, or freeze them for smoothies. The rest of the fruit is best left in long sections for grilling which you can split lengthwise if you want. Fire up the grill. Once hot, set a your long chunks on the grate. After a few minutes the sugar will caramelize and darken. Turn the pineapple several times to get good color all over.

Grilled Pineapple Aviation
2 oz gin
.75 oz lemon juice
2 chunks Grilled pineapple
6 leaves Mint
.75 oz Simple syrup

In a mixing glass, muddle the mint leaves and pineapple chunks. Add gin, lemon and ice. Shake and double-strain into a chilled cocktail glass. Garnish with a mint sprig and a pineapple chunk.

House Spirits suggests using their Aviation Gin—easy for us since it is distilled here in Portland just down the hill and across the river. We try to always have a bottle on hand, but you can't go wrong with Plymouth either which has a similar citrus-forward flavor profile. Actually, we've made fantastic Southside cocktails with any London Dry gin, and this will work well with whatever you have.

Slice the grilled pineapple into one-inch chunks. You'll need three chunks per drink: two that you muddle in the shaker and the third for garnish. You need to press the chunks with your muddler to squeeze the juice out of the fruit. It's not as important to hit the mint, in fact, it's better if you don't abuse it. Add the rest of the ingredients plus plenty of ice, especially if your pineapple is still a bit warm. Shake this one very hard to bust up the mint leaves and thoroughly chill the drink. It's best to double strain it through a second fine-mesh strainer. This will filter out any charred bits and pieces of mint. The pineapple juice also creates a lovely layer of foam at the end, so take your time to get it all.

Not only is this a fun drink to make by the grill, but pineapple cooked this way makes a delicious side for any meal. The flavor of the cocktail is nicely balanced with the pineapple present, though it doesn't overwhelm the drink. We were expecting a bit more char flavor but perhaps the effect is more of a transformed caramelized pineapple juice and less about the fire. Ours is a gas grill, but had we added some wood chips to create a little smoke or grilled over charcoal the effect might be different (if you try it over wood or charcoal, let us know). In any case, the gin works nicely in this drink to uplift the other flavors. We love the combination of a little mint and sweetened lemon, and pineapple is a great addition. Kelly suggests trying watermelon or peaches too—the possibilities are limited only by what you have available. We served ours in this classic coupe available in the Summit Sips glassware store.