
A new cup for your baby needs to, first and foremost, work well for your baby. To allow for smooth transitions you will want to try to avoid making a transition that is too abrupt for your child.
For example, you wouldn’t necessarily want to go directly from a bottle with a nipple (slow) to a cup with a straw (fast). Just think about it from your baby’s perspective; with the bottle, your baby knows to tip it back and they don’t realize (of course) that the flow is regulated. This would lead them to assume that anytime they tip a drink back that the flow will be as it is with a bottle: slow… so with a straw cup, not only will your baby get too much to drink in one sip, but they will also need to learn a new sucking method. They would also not find much success in tipping the cup back. This experience would be overwhelming and frustrating for your baby and they will understandably want their bottle back. Oh, and if the goal is to teach your baby not to suck when drinking, a straw will not accomplish that. This is so confusing, right?! So if you are like me you are now thinking, “then just tell me exactly what I need to do, I have 5 minutes until this baby wakes up from his/her nap”.
Well, if you see this post soon enough you can try doing what I did and see if it works for you. Perhaps you will want to do some more research, but either way follow someone’s advice. You would be surprised how fast you can end up with a graveyard of cups, and too many cup introductions might lead to a suspicious and confused little one who could end up becoming resistant to trying new cups, among other things. Oh, and cups are kind of expensive too, so don’t waste your money on the ones that aren’t the right stage for your child or those that leak!
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If you have been following me you know that I recommend starting your baby off with the Dr. Brown’s Options standard neck bottles. This is based not only off my own experiences, but the experiences of my closest mom friends. Consider us your mom friends an read more about why here.
If you already use these bottles, your first transition from nipple to spout can be pretty easy. You can try purchasing the Dr. Brown’s Spouts. I didn’t know about these when we made our transition, but I hear that it has helped some moms with babies who don’t want to give up their bottles.
Nuby No-Spill Super Spout Grip N’ Sip Cup

The Nuby Cup is a good first sippy cup to offer because it has a soft spout, which is what they are used to and easier to transition to as well as handles which are a convenient and fun addition. We transitioned to the Nuby directly from the bottle. It really doesn’t leak much. The no-spill spout works well, especially at first, but expect that your child will gnaw on it and depending on how many teeth they have, the spout will split and leak a tiny bit when held upside down. Even with that, I do believe it is an excellent transition cup from a bottle. When the spouts leak, it may be a fair signal to move on to the next phase cup.
Munchkin Miracle 360 Cup Trainer Cup
The Miracle 360 cup is pretty neat. It teaches your baby/toddler the method for drinking out of a real cup; only when pressure is applied to the lid is the drink released. It pretty much has all the benefits and feels of drinking out of a real cup, except that leaks are prevented with the miracle lid. The only exception is when your child drops this cup on the ground, there is generally a splatter of the liquid that is built up into the lip of the lid. As a result of using this cup, your child continues to tip their drink back, but learns that “sucking” is not necessary to take a drink. They essentially understand what it feels like to drink out of a real cup, but they don’t realize that holding it over their head would get them wet if they were actually using a real cup. This will be clear when they grab one of your cups off the coffee table and throw it back. It is a great cup that doesn’t get ruined over time and can be continued to be used for quite some time, especially when you are in the car and you want to prevent leaks. I later discovered that Munchkin also offers a stainless steel option that is not cheap for a toddler cup, but is great for keeping milk cold on the go (or just in the morning from wake-up until nap time). I use this similarly for my daughter as I use my own Yeti Rambler Tumbler cup.
In my opinion, the last transition that you really need to make is to a regular straw cup. There are 2 great options, and you may want one or both of these depending on your needs.
Contigo Kids Tumbler

Contigo Kids Tumbler with Straw– My daughter loves this “big girl” cup because I think it reminds her of the cups she gets at a restaurant. I love that the has the independence of a big kids cup, but in reality it is suitable for her to operate on her own. Word of advice, use it seated if you can. Like any straw cup, the hard straw will not be fun when paired with a fall.
Thermos Funtainer

Thermos Funtainer– This is a great straw option for on the go, but you may choose to use it for all purposes. It is great for keeping a drink cold. Straw can be replaced if your child chews it. Sometimes they do leak over time, but hey, they all do!