Open Cricut Design Space. You can find my ocean themed glasses cut file project here. I used the font BFC Paris for the names.

Use your measuring tape to measure your glasses, then size your designs to the size that you would like for your cups.

Duplicate the design for as many cups as you will be making.

Click Make It. Follow the instructions on your screen to connect your Cricut to you computer or device and select your cutting material.

If using Smart Vinyl feed your vinyl into your machine with the color side facing up. If using regular vinyl lay your vinyl on your cutting mat with the color side facing down. You may want to run a brayer over your vinyl to push it down onto the mat and firmly adhere it.

When your design is done cutting, unload your cutting material/mat from your machine and use your weeding tools to weed your vinyl, removing the vinyl from around your design leaving just the design behind on the white paper backer.

For my cups I used transfer tape to transfer the names onto the cups, but placed the other decals by hand almost like stickers.

To use transfer tape, cut the name out of your sheet of vinyl so that you just have the name on the white paper backer. Cut a piece of transfer tape slightly larger than your design. Peel the paper backer off the back of your transfer tape and lay the transfer tape on top of your vinyl design with the sticky side of the transfer tape facing down. Run your scraper tool over the front and back of your design, pushing the design onto the transfer tape. Peel up your transfer tape carefully, making sure your design transfers up with the tape. Position your design on your cup, run a scraper tool over top, then peel away your transfer tape revealing your design beneath.