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DIY Pineapple Cocktail Glasses with Cricut Premium Vinyl

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As I move into summer entertaining, one of my favorite elements to add to any party is custom glassware. I love planning themed cocktails for parties, and by adding a personal touch to my glasses I wow my guests with my Pinterest-worthy drinks. Using Cricut Premium Vinyl and a fabulous pineapple that is included in the Martha Stewart exclusive designs in Cricut Design Space, I created a set of gold Pineapple Drinking Glasses for an upcoming summer pool party. Keep reading for this easy Cricut Vinyl project tutorial (and check out some of the other easy DIY party supplies that use Cricut vinyl!)

This post and the photos within it may contain affiliate links. If you make a purchase through one or more of the links, I may receive a small commission at no extra cost to you.

Pineapple Cocktail Glasses - Make Cricut Vinyl Projects with your Cricut by Pineapple Paper Co.

Martha Stewart Cricut Explore Air 2

Last month we were incredibly excited to share our Magical Unicorn Party that was the first project we created in collaboration with Cricut, Michaels, and Martha Stewart. We are lucky to be using our Cricut® Explore Air™ 2 Special Edition, Martha Stewart Machine Bundle over the next year to share DIY Projects that you can make using your Cricut Machine. I crafted the Unicorn party down to the tiniest of details, from customizing balloons, to cupcake wraps, to a unicorn birthday t shirt! In order to feature additional Martha Stewart Celebrations collection, I’ve also designed an Outdoor Peach Party, a Dinosaur Birthday Party, a Halloween Cake Topper, and a Reverse Canvas Project.

The new Martha Stewart Cricut Explore Air 2, which is available exclusively at Michaels, makes it so easy to create professional quality personalized items for all of my parties (and I love to entertain!) and is the hardest working tool in my craft room. I also love that this Cricut Explore Air 2 model is a pearl color with gold details (yay!)–it looks pretty and cuts and writes up to 2x faster than previous Explore models! It can cut over 100 different materials, from the new Cricut Premium Vinyl to Iron On, Glitter Paper, Foil, and Faux Leather.

The NEW Cricut Premium Vinyl has been redesigned to make your DIY projects even easier to create! When making previous projects, sometimes using vinyl was a STRUGGLE. It bubbled, it didn’t cut the whole way through, or it didn’t work well with any transfer tape. Well, I’m happy to let you know that I’m in LOVE with the new Cricut Premium Vinyl! Normally I would avoid making glasses or other projects with small cuts like in the pineapple design I used for these drinking glasses. I couldn’t believe how different my user experience was using the new Premium Vinyl! The small pieces cut perfectly on the Martha Stewart Cricut Explore Air 2, and the new smooth release technology made it possible for me to weed the design in nearly one piece! In addition, when using Standard Grip Cricut Transfer Tape, I was amazed at how easy it was to transfer my design from the backing sheet to the glass.

What you need to make Pineapple DIY Cocktail Glassware

In order to make your own DIY Pineapple Drinking Glasses with your Cricut vinyl, you’ll need the following supplies:

Cricut® Explore Air™ 2 Special Edition, Martha Stewart Machine Bundle (available exclusively at Michaels)

Cricut Blue or Green Cutting Mat

NEW Cricut Premium Vinyl, Everyday Sampler (or Gold Premium Vinyl), also available at Michaels.

Cricut Standard Transfer Tape

Cricut Tool Set (the Martha Stewart Explore Air 2 comes with a set of gorgeous gold tools!)


The Everyday Sampler of Cricut Premium Vinyl has great neutral colors included; I always find myself using neutrals more than anything. You could make a ton of projects with this pack of 6 sheets of Cricut Vinyl.

Included with your purchase of the Cricut Explore Air 2 Special Edition, Martha Stewart Bundle is a set of almost 50 FREE images that you can use to start projecting. I loved using the Martha Stewart pineapple for my vinyl design, of course! By combining the pineapple with a Cricut font in Design Space, you can use the design file we created! Click the following link to head over to use and customize the pineapple design:

Click to Make: Cricut Vinyl Pineapple Drink Glasses

You can size the images to fit the glasses you’d like to use for your project by resizing the grouped designs:

After you have the design sized (and as many pineapples as you need) on your canvas, click the “Make It” button. Because this design isn’t going to be used for iron-on purposes, you don’t have to use a mirrored image.

Set the dial on your Cricut machine to “Vinyl” and you’re ready to cut!

You’ll notice in the above picture that I like to use my Green “StandardGrip” mat; I like how well the Cricut vinyl sticks and I don’t have to worry about it moving around while cutting.

Once your designs have finished cutting, cut them apart and remove the excess vinyl (weed the design). These pineapples were SO easy to weed with the redesigned smooth release technology. You’ll need the standard Cricut Transfer Tape (SHOP Cricut Transfer Tape) for the new Premium Vinyl and your Cricut Scraper that’s included in the Tool Kit (some people use other tools to apply vinyl, but I’ve always used this scraper).

After applying the Transfer Tape, I like to flip my design over and run the scraper over it to make sure the vinyl is adhered to the tape:

If you try to line up the grids on the transfer tape, it will help when applying to your glass.

The final step is to remove the transfer tape and vinyl design from the vinyl carrier sheet and apply to your glasses. Just position the design and run your scraper or fingers firmly over the design to adhere to your glasses, and then peel off the transfer tape.

I absolutely love how these DIY gold pineapple drink glasses turned out, and I know my guests will love them! And since Cricut Premium Vinyl is removable, even though they are strongly adhered, after the party I can easily remove the pineapple design and use the glasses for another party (and another design!)

We will also be sharing the fresh Pineapple Mojito recipe we used to fill these awesome DIY Pineapple Glasses! If you don’t want to miss our pineapple cocktail recipe or other DIY Martha Stewart projects, Sign Up for our Email List–You’ll get updates on our most recent crafts, and exclusive access to our FREE designs and sales at the Pineapple Paper Co. Shop!


Magical Unicorn Birthday Party with Martha Stewart, Cricut, and Michaels

How to Make Minnie Mouse Birthday Party Ideas with Cricut

Host an Outdoor Party with Martha Stewart, Cricut, and Michaels

Flamingo and Pineapple First Birthday Party Ideas

Dinosaur Birthday Party with Martha Stewart, Cricut, and Michaels

Fall Birthday Party Ideas

American Girl Birthday Party Ideas

The Best Mermaid Birthday Party Ideas

This is a sponsored conversation written by me on behalf of Cricut. The opinions and text are all mine.







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about charynn


Hi, y’all! I’m Charynn, the owner and designer of Pineapple Paper Co. I’m a mom of four kids (two girls and two boys) living in Pittsburgh. I love hand lettering, anything southern, cocktails, and of course, pineapples! I am excited to share my SVG files, printables, and craft projects with you! The pineapple is a symbol of hospitality, and I welcome y’all to my little corner of the internet. Read more…

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  1. Judi Johnson says:

    I have gone to Design Space 2 times and could not find the pineapple design. I even typed in Pineapple Drink Glasses. How do I find the cut file?