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drill holes in planters?
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Sure, just use a small drill bit to begin with and then a larger drill bit. Less chance of it cracking then.
I'm presuming it's unglazed terracotta, which is porous and therefore is less likely to become waterlogged, but a few drainage holes is pretty essential, especially as herbs are often quite drought tolerant and don't like boggy conditions.
Edit to add that strawberry planters do have planting holes along the sides which also work in draining away excess water, so you would only want a couple of small holes at the bottom to provide drainage for the lowest herbs.0
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