Pina Colada Cookies

I promised an “advanced” cookie so here it  is…

I generally shy away from this type of tutorial for two reasons.  It’s difficult to break down on my end {as in the super-stressful wondering if I forgot anything kind of difficult} and I also worry it might be discouraging from a beginner’s standpoint.

Some cookies are more of trial and error than a clear-cut design plan. No matter how much planning you do,more often than not, things don’t work out the way you envisioned.  It’s not until you begin that it becomes obvious that the plan is NOT going to work. 

This is my first ever pina colada cookie {I won’t even tell you how long it took me to make these} The ones you see today is how they’ve evolved as my decorating skills improved.  There is about a two year jump between these cookies.  Also, I thought it would be funny to mention, the black outlining here was NOT planned, but rather a fix, because this cookie did not turn out at all like I’d expected!

Here is another attempt

And these are actually the first cookies I made for this post, then ended up hating…Bad for me, but good for my friend Lilly because she got the cast-offs this time…

 Bottom line is it took me two years to make a cookie I’m mostly happy with. 


Broken down this might seem pretty simple, but when you’re starting with a blank slate, something like this is pretty scary, so, I’m here to walk you through the process.

Are you READY?!   *I said that in my best basketball announcer voice*

Begin with these three cutters, a necktie, which you can get from Sweet Candy and Baking Supplies, a 1 1/4 inch round, and a heart.  Each one makes up a part of the final cookie.  The tie is the glass, the round is for the pineapple, and the heart for the umbrella.


Use these cutters and my cookie dough recipe to piece together the pina colada cookie.  The umbrella part is a little tricky so I made a little visual aid to help.  Use the end of the heart to create a triangle shape.  Cut across the end with a spatula so it’s straight.

Then, position the tie cutter so that it looks like the umbrella has been dropped into the drink, and use it to trim the umbrella piece.


Bake them together, then you are ready to decorate.

To decorate pina colada cookies you’ll need:

  • White piping icing for the glass
  • sky blue, white, and light yellow flood icing for the glass {make them all somewhere in between 10-second and 20-second icing}
  • light yellow sanding sugar
  • brown piping icing for the pineapple
  • dark yellow, and warm brown flood icing for the pineapple
  • red twenty second icing for the cherry
  • two colors of flood icing {your choice} for the umbrella
  • coordinating piping icing to outline the umbrella
  • medium-stiff piping icing with a star tip {I used a #28 but a #16 will work fine} for the whipped cream

Now we’re ready to go.  Begin by putting a large round dot of white flood icing on the tie cookie.

Next, use the purple flood icing to fill in the umbrella shape

Immediately afterward, swirl in the coordinating umbrella color

Then, begin outlining the glass.  I add the top rim first to act as a guide, so I can visualize how I want the rest of the outline to look.

Starting at the top and working down to the stem, add the sides, then the base.

At this point, fill the base, the inside of the glass, and add a cherry on top.

Let that dry for about twenty minutes, and then begin working on the pineapple slice.  To do this, fill in the dark yellow icing and add a strip of warm brown.  Swirl that in with a toothpick, then use brown piping icing for the outer edge of the pineapple slice.

Let that dry for another twenty or thirty minutes and then using some sort of star tip, add whipped cream.  I did not make my icing super stiff because I didn’t want anyone breaking their teeth biting into this cookie.  It had just enough body to keep a bit of shape, but it was thin enough that it stayed soft.

Now relax…let that dry overnight.  Have a cocktail if you need it.

  The next day, flood the inside of the glass.  See that weird swirly effect in the icing?  That’s NOT a good thing.  That’s what happens when you use day-old icing, and don’t stir it well before using it again.  Normally this would be a “scrape mistake”.  Icing like this usually leaves porous swirls and craters as it dries.  But since it was being covered with sanding sugar, I let it slide.

Let the flooded portion dry for a minute or two, then cover with sanding sugar.

Then add all of the other details

When they’re dry, if you survived the decorating process, you’ll have beautiful pina colada cookies. You may want need a real one also.

 Like I said, it only took TWO YEARS but I’m finally pretty close to the cookie in my head.

It may not be something you’d make for an everyday occasion, but it gives you an idea of what goes into designing and decorating a detailed cookie like this.


Now, off for a pina colada of my own…or maybe a pina colada cupcake like the ones my friend Kristan made…after explaining that, I need something


Yes, a cupcake it is.  I’ll meet y’all there. She’ll be happy to see us.  She’s moving and she pays helpers in cupcakes!

I’m linking up with these FUN blogs!


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