Here's my first attempt at using my Cricut to DIY wine glasses! There are some bubbles, but you can only tell close up and it's really hard to tell on the black.
What I used:
Tie the Knot cartridge
Outdoor vinyl for circut machines bought on eBay (put on outside of glass - can be hand washed)
Size 3 for monogram
Size 1.5 for flourish design - real dial size on