For intricate details (like these gorgeous curlicues), you'll achieve best results with a flat-sided pumpkin. And for these spray-painted pumpkins, it doesn't matter if the flattest side happens to be the prettiest -- it all receives a nice coat of paint to cover imperfections. So swivel to the flattest side and carve away!
1. Hollow out your pumpkins from the bottom (not the top), and scrape the wall thinnest that you're planning to carve. (No thicker than 1" is ideal.)
2. Spray both pumpkins with black spray paint, and allow them to dry completely.
3. Tape your printed stencil patterns to the pumpkins, and use a pin tool to tap in pin pricks into the pumpkin, following along the stencil lines. Keep pin marks closely spaced -- you'll use them as guides for carving and etching. Remove the paper patterns when all lines have been transferred.
4. For the wineglasses: Use a gouging tool to scrape away the pumpkin's surface skin inside the glass outlines but outside the curlicues. (The curlicues should remain black.) Use a skinny, serrated knife to carve the top and bottom sections of the wineglasses; press gently from inside the pumpkin to pop these sections outward.
5. For the bottle: Use a gouging tool to remove the pumpkin's surface skin inside the bottle outline but outside the curlicues and label. (Both curlicues and label should remain black.)
6. Light the pumpkin interiors with candles to enjoy the flickering glow.