First, wet your glass-of-choice then put it in the freezer before hand so your ice isn't wasted cooling it off. I like beer mugs as they have a handle.
Use a fresh pineapple. If you can easily pluck an inner-most leaf out of the top, it's ripe. Trim about an inch or so off of both top & bottom. Next, stand on end and slice down the outside about 1/2" in, following the contour to take off the rough exterior. If "eyes" remain, you didn't go deep enough in. Rotate & repeat.
Then slice down the middle lengthwise. Next, with one round side facing down, slice right down the hard, center core with a very sharp knife. If you're not comfortable doing this, then turn it over, flat side down. But you may slice the core unevenly, making it harder to remove.
Lay a quarter down flat and go in at a 45° angle to slice out the core. Then slice each quarter length-wise in two. Slice these cross wise about 1" thick into chunks.
Note: I rarely use "triple sec" anymore because most have very little orange flavor, no depth and are very, very sweet. There's just not much there, there. Instead orange liqueurs are better, but most (Grand Marnier) are very expensive. I use Le Grand Mar-Salle orange liqueur found at Spec's Liquor. It's about $14/750ml. Another excellent choice here is Grand Gala. Compare these to 3sec side-by-side and you'll never go back.
3 Cups pineapple chunks
1 Cup lime juice
1 Cup 100% Agave tequila
1/2 Cup Orange Liqueur
Puree the pineapple chunks in a Cuisinart or blender. Add the remaining and mix (be sure your Cuisinart is big enough so it won't overflow!)
Taste and adjust as necessary. I make mine on the strong side because they're about to be shaken with ice, which if you use too much, will dilute them too much. Also, it's so [censored] hot down here, ice will quickly melt outdoors, further diluting your drink.
Put a hand-full of ice cubes into a shaker and add about 10oz of mix. Shake for at least 20 sec. Strain into a salted rimmed beer mug with more ice.
Salt is important as it counters the limes bitterness very well. However if you must leave it out......
You can make these "frozen" but they'll have to be stronger. They'll also quickly become watery if it's hot outside and they're not readily consumed. Up North, you may not have a problem with this, but down here.....we have to double coozie beer bottles just to keep them cool for awhile.