Grow bags

Yes to both, I shove the canes I’ll use for support through the whole bag a few times to make holes. Good luck.

Ah thanks Patsy. It never occurred to me to make holes in the bags. Maybe that's why I've never had success with tomatoes.
I grow cucumbers and lettuce successfully without drainage!

Yes, we always grow tomatoes in deep grow bags in the greenhouse very successfully and have been doing so for years. You can makes holes in the bottom of the bags by piercing with a garden fork.