Hardiness Zone: 9a
In general the more soil you are able to give a veggie plant, the healthier it will be. It is easier to keep large pots from drying out and there are more nutrients available. Remember, if the volume of 2 containers is the same, the one with more surface area will dry out quicker.
If you use the 5-gallon bucket, you can poke one of those wire tomato supports into the soil and train the cucumber up it.
I think you could use either one. My neighbor has one of those whiskey barrels and she has a tomato in the center and cukes along the sides of it. She is hoping they will drape over the edge.
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