The short version
The sippy cup that works is the one you can take apart and clean. Offer a cup from 6 months, aim to be off bottles around 12 months, and move to an open steel tumbler as soon as the child manages it.
What happened
The paediatrician said to start offering water in a cup at six months, and to be off the bottle by around a year. I nodded and bought a sippy cup like it was one decision. It was four.
Cup one had a soft spout, a handle on each side, and a valve so it wouldn't leak. He couldn't get anything out of it. Going by the instructions, the valve needed more suction than a seven-month-old had, so he'd bite the spout, get nothing, and throw it. I checked I'd assembled it correctly; I had. It just didn't suit him at that age.
Cup two was a straw cup. Better; he worked out the straw in two days. The straw was also impossible to clean properly, and after a fortnight I found something green in it that I'd rather not describe. Straight into the bin.
Cup three was the famous 360 cup, the one that lets a child drink from any edge like a real cup. I loved the idea. Ours leaked in the diaper bag twice and then the silicone rim came off in his hands. Maybe a bad unit, maybe my fault for over-tightening. Either way, three strikes.
Cup four was the cheapest: a two-in-one that came with a soft spout and a straw, both of which could go in the dishwasher basket in pieces. Nothing clever. He used it from ten months until he was happy with an open steel glass at around twenty months. The cleverest cup lost to the one I could clean.
The AAP and NHS both suggest introducing a cup from around six months and weaning off bottles around 12 months, mainly because prolonged bottle use is associated with tooth decay. For eating and drinking, every major guideline wants the baby sitting upright with good head control, in a high chair or seat, not reclined.
AAP, Starting Solid Foods. Source · CDC, Choking hazards (2026): sit up to eat, no lying down, crawling or walking. SourceThe verdicts
Mee Mee 2-in-1 spout and straw sipper, 150 ml
The survivor. Two mouthpieces, every part comes off, nothing hides. Plain and it worked for ten months.
A small steel tumbler (any kitchen)
The actual goal. We started offering it at a year with a finger of water in it. By twenty months he preferred it.
Cubworthy, with a catch
Munchkin Miracle 360 cup, 177 ml
Loved the idea. Ours leaked in the bag and the rim came loose. Other mums swear by it, so maybe a bad unit; I wouldn't buy again.
The valved soft-spout cup that did not suit us
The design didn't work as I had hoped at seven months. I would check the exact model and its instructions before buying a similar one, rather than assume every cup works the same way.
Product details are as we used them; the version on sale now may differ. Check the exact model and the manufacturer's instructions.