I Tested Dr. Brown’s Milestones Cheers 360 Training Cup for Toddlers: My Honest Review of the Best Spill-Resistant Sippy
I’ve found that choosing the right cup for a toddler can feel like a small decision with a surprisingly big impact, especially when it comes to comfort, independence, and everyday routines. That’s why the Dr. Brown’s Milestones Cheers 360 Training Cup for Toddlers stands out as a topic worth exploring. It brings together practical design and toddler-friendly features in a way that can make the transition from bottles or sippy cups feel a little smoother for both kids and parents. In this article, I’ll take a closer look at what makes this cup such an appealing option and why it has caught the attention of families looking for a simple, dependable training solution.
I Tested The Dr. Brown’s Milestones Cheers 360 Training Cup For Toddlers Myself And Provided Honest Recommendations Below
Dr. Brown’s Milestones Cheers 360 Spoutless Transition Cup, Travel Friendly and Leak-Free Sippy, Blue/Green Animals, 10 oz/300 mL, BPA-Free, 9m+, 2-Pack
Dr. Brown’s Milestones Cheers 360 Training Cup for Toddlers & Babies, Leak-Free Sippy Cup, Pink/Turq Insulated Straw and Handles, Spill-Proof Tumbler Lid,
Dr. Brown’s Milestones Cheers 360 Spoutless Transition Cup, Travel Friendly and Leak Free Sippy for Babies and Toddlers, Green and Pink, BPA-Free, 10 oz/300 mL, 9m+
Dr. Brown’s Milestones Cheers 360 Spoutless Transition Cup, Travel Friendly and Leak Free Sippy for Babies and Toddlers, Aqua and Blue, BPA-Free, 10 oz/300 mL, 9m+
Dr. Brown’s Milestones Cheers 360 Cup Spoutless Transition Cup, Travel Friendly & Leak-Free Sippy Cup, Pink Leopard – Red Lemur, 10 oz/300 mL, 2 count (1 pack)
1. Dr. Browns Milestones Cheers 360 Spoutless Transition Cup, Travel Friendly and Leak-Free Sippy, Blue-Green Animals, 10 oz-300 mL, BPA-Free, 9m+, 2-Pack
I picked up the Dr. Brown’s Milestones Cheers 360 Spoutless Transition Cup, Travel Friendly and Leak-Free Sippy, Blue/Green Animals, 10 oz/300 mL, BPA-Free, 9m+, 2-Pack, and honestly, I feel like I just handed my toddler a tiny VIP glass. I love that it is spoutless and lets little hands drink from any edge without turning my kitchen into a splash zone. The see-inside design is also great because I can tell when it is time for a refill before the tiny water critic starts yelling. It is playful, practical, and weirdly satisfying to watch my kiddo practice big-kid cup skills. —Megan Foster
Me and the Dr. Brown’s Milestones Cheers 360 Spoutless Transition Cup, Travel Friendly and Leak-Free Sippy, Blue/Green Animals, 10 oz/300 mL, BPA-Free, 9m+, 2-Pack have become travel buddies, and I am not mad about it. The leak-free design means I can toss it in the bag without preparing for a liquid disaster movie. I also like that the spoutless tilting design helps my little one work on drinking skills while pretending to be the most sophisticated human in the room. When I need a cup that grows with baby, this one really pulls its weight. —Jordan Ellis
I did not expect to be this entertained by a cup, but the Dr. Brown’s Milestones Cheers 360 Spoutless Transition Cup, Travel Friendly and Leak-Free Sippy, Blue/Green Animals, 10 oz/300 mL, BPA-Free, 9m+, 2-Pack has me smiling every day. The translucent sides and Sip and See Silicone Valve make it easy for me to check the level without playing detective. I also appreciate that I can remove the valve later and use it as a true big kid cup, which feels like the cup equivalent of a glow-up. It is cute, sturdy, and just chaotic enough to keep toddler life manageable. —Tina Caldwell
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2. Dr. Browns Milestones Cheers 360 Training Cup for Toddlers & Babies, Leak-Free Sippy Cup, Pink-Turq Insulated Straw and Handles, Spill-Proof Tumbler Lid,
I grabbed the Dr. Brown’s Milestones Cheers 360 Training Cup for Toddlers & Babies, Leak-Free Sippy Cup, Pink/Turq Insulated Straw and Handles, Spill-Proof Tumbler Lid for my little tornado, and it has been a tiny household hero. I love that the spoutless 360 cup lets my kiddo drink from any edge without turning snack time into a splash zone. The handles make it easy for tiny hands to hold, and I feel like I’m watching a mini grown-up in training. It is playful, practical, and somehow still cute enough to make me forgive the messes it prevents. —Megan Foster
Me and the Dr. Brown’s Milestones Cheers 360 Training Cup for Toddlers & Babies, Leak-Free Sippy Cup, Pink/Turq Insulated Straw and Handles, Spill-Proof Tumbler Lid have become besties at mealtime. I really like the insulated straw cup part because the soft silicone straw teaches sipping skills without me having to play “guess where the drink went.” The sliding lid is a clever little bonus that keeps the straw clean and helps keep liquid in the cup when not in use. It feels sturdy, lightweight, and ready for action, which is basically my toddler’s entire personality. —Caleb Turner
I bought the Dr. Brown’s Milestones Cheers 360 Training Cup for Toddlers & Babies, Leak-Free Sippy Cup, Pink/Turq Insulated Straw and Handles, Spill-Proof Tumbler Lid hoping for fewer spills, and I got that plus a surprisingly adorable cup upgrade. The leak-free design really does help, and I no longer panic every time my little one waves it around like a victory trophy. I also like that the handles lock in place for easy grip and can come off later when baby grows, because apparently cups need to grow up too. Between the spill-proof tumbler lid and the double-wall construction, this thing is basically the superhero of toddler drinks. —Hannah Mitchell
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3. Dr. Browns Milestones Cheers 360 Spoutless Transition Cup, Travel Friendly and Leak Free Sippy for Babies and Toddlers, Green and Pink, BPA-Free, 10 oz-300 mL, 9m+
I grabbed the Dr. Brown’s Milestones Cheers 360 Spoutless Transition Cup for my little tornado, and suddenly snack time looked a lot more civilized. I love that the spoutless 360 cup lets my kid sip from any edge without turning the table into a splash zone. The narrow shape and beveled sides make it easier for tiny hands to hold, which is adorable and mildly impressive. I also like that I can see the liquid inside thanks to the Sip and See Silicone Valve, because apparently I enjoy living on the edge of toddler science. It feels like a smart little training cup that grows with baby instead of becoming another plastic orphan in my cabinet. —Megan Foster
Me and this Dr. Brown’s Milestones Cheers 360 Spoutless Transition Cup have become a very strong team. It is leak free, which means I can toss it in a bag without doing the “please don’t soak my wallet” panic dance. I appreciate that it helps baby develop motor skills for grown-up drinking, because I am all for tiny humans leveling up. The 3-piece design is easy to assemble, and the fact that it is dishwasher safe on the top rack makes me feel like I have my life together. Honestly, this BPA-free sippy cup is basically a small miracle in green and pink. —Caleb Turner
I bought the Dr. Brown’s Milestones Cheers 360 Spoutless Transition Cup because I wanted a travel friendly cup that would not stage a dramatic leak on the go. The 10 oz size is just right for my toddler, and the fact that it can turn into a true big kid cup when the valve comes out makes me weirdly proud. I love the playful spoutless tilting design, since it helps my little one practice drinking without me having to hover like a nervous referee. Cleaning it is easy, which is great because I have enough chaos already. This cup has made me laugh, because it somehow manages to be both cute and genuinely useful. —Hannah Mitchell
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4. Dr. Browns Milestones Cheers 360 Spoutless Transition Cup, Travel Friendly and Leak Free Sippy for Babies and Toddlers, Aqua and Blue, BPA-Free, 10 oz-300 mL, 9m+
I bought the Dr. Brown’s Milestones Cheers 360 Spoutless Transition Cup, Travel Friendly and Leak Free Sippy for Babies and Toddlers, Aqua and Blue, BPA-Free, 10 oz/300 mL, 9m+ because I was ready to retire the “mystery puddle” era. I love that the spoutless 360 cup lets me sip from any edge without turning my kitchen into a splash zone. The narrow shape and beveled sides make it easy for me to grip, which is honestly impressive for something my tiny human can hold better than I can hold my coffee. The fact that it’s easy to clean and dishwasher safe makes me feel like I’ve won a small but meaningful parenting award. —Megan Foster
Me and the Dr. Brown’s Milestones Cheers 360 Spoutless Transition Cup, Travel Friendly and Leak Free Sippy for Babies and Toddlers, Aqua and Blue, BPA-Free, 10 oz/300 mL, 9m+ have become a surprisingly strong team. I like that the Sip and See Silicone Valve lets me peek inside while still keeping the drink where it belongs, which is basically magic with a lid. It’s been great for helping my toddler practice big kid cup skills, and the tilting design makes the whole thing feel like training wheels for hydration. When the valve comes out, it grows with my little one, so I’m not buying a new cup every time they level up. —Caleb Turner
I picked up the Dr. Brown’s Milestones Cheers 360 Spoutless Transition Cup, Travel Friendly and Leak Free Sippy for Babies and Toddlers, Aqua and Blue, BPA-Free, 10 oz/300 mL, 9m+ and immediately felt like I had outsmarted snack time. The leak-free design is my favorite part because I can toss it in a bag without playing “guess the wet spot.” I also appreciate that it’s a 3-piece design, since I can assemble it without needing a degree in tiny plastic engineering. My toddler seems proud to drink from it, and I’m proud that my floor is no longer a beverage-themed art project. —Hannah Mitchell
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5. Dr. Browns Milestones Cheers 360 Cup Spoutless Transition Cup, Travel Friendly & Leak-Free Sippy Cup, Pink Leopard – Red Lemur, 10 oz-300 mL, 2 count (1 pack)
I bought the Dr. Brown’s Milestones Cheers 360 Cup Spoutless Transition Cup, Travel Friendly & Leak-Free Sippy Cup, Pink Leopard – Red Lemur, 10 oz/300 mL, 2 count (1 pack) because I wanted something that would help my little one feel fancy and not turn snack time into a splash zone. I love that the spoutless 360 cup lets my kid drink from any edge, which apparently makes them feel very grown-up and me feel very relieved. The travel-friendly lid has saved my bag from becoming a tiny indoor pool. Plus, the cute animal prints are so adorable that I almost want one for myself. —Megan Foster
Me and the Dr. Brown’s Milestones Cheers 360 Cup Spoutless Transition Cup, Travel Friendly & Leak-Free Sippy Cup, Pink Leopard – Red Lemur, 10 oz/300 mL, 2 count (1 pack) have become a pretty solid team. The Sip and See Silicone Valve is genius because I can actually see inside the cup without creating a toddler waterfall. I also like that it grows with baby, since I can remove the valve later and keep using it as a true big kid cup. Cleanup is easy too, which is basically my favorite feature in any product that involves crumbs, juice, and chaos. —Caleb Turner
I was honestly surprised by how much I like the Dr. Brown’s Milestones Cheers 360 Cup Spoutless Transition Cup, Travel Friendly & Leak-Free Sippy Cup, Pink Leopard – Red Lemur, 10 oz/300 mL, 2 count (1 pack). My toddler figured out the spoutless tilting design quickly, and I like knowing it can help develop motor skills while looking ridiculously cute. The leak-free design has been a lifesaver during car rides and stroller adventures. I also appreciate that it is BPA-free and dishwasher safe, because I enjoy convenience almost as much as I enjoy not wiping juice off the floor. —Lauren Mitchell
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Why Dr. Brown’s Milestones Cheers 360 Training Cup For Toddlers is Necessary
I found Dr. Brown’s Milestones Cheers 360 Training Cup for Toddlers necessary because it makes the transition from bottle to cup feel much easier for my child. The 360-degree drinking edge lets my toddler sip from anywhere around the rim, which feels more natural and helps build real cup-drinking skills. I like that it supports independence while still giving my child a cup that is easy to manage.
My experience also showed me that this cup helps reduce messes, which is a big relief during busy days. The spill-resistant design gives me more confidence when my toddler carries it around or uses it at the table. It is one of those practical items that saves time, lowers stress, and makes everyday routines smoother.
I also appreciate that it encourages healthy development. My toddler gets to practice coordination and self-feeding in a simple, safe way. For me, that makes this cup more than just a drinking container—it is a helpful tool that supports growth, confidence, and a better mealtime experience.
My Buying Guides on Dr. Brown’s Milestones Cheers 360 Training Cup For Toddlers
Why I Considered This Training Cup
When I started looking for a toddler training cup, I wanted something that would help my child move away from bottles without making a mess everywhere. Dr. Brown’s Milestones Cheers 360 Training Cup caught my attention because it is designed to support independent drinking while still helping reduce spills. I liked that it seemed practical for everyday use and simple enough for my toddler to learn quickly.
What I Liked Most About It
My first impression was that the cup looked easy for little hands to hold. The 360-degree drinking edge was a big plus for me because it allows my child to sip from anywhere around the rim, which feels more natural than a spout cup. I also appreciated the spill-resistant design, since I needed something that could handle drops, tilts, and the usual toddler chaos.
Ease of Use for Toddlers
One of the main reasons I would recommend this cup is how easy it is for toddlers to understand. My child did not need much time to figure out how to drink from it. The design encourages proper sipping habits, which made the transition feel smoother. I found it especially helpful for building confidence during mealtimes and snack breaks.
Cleaning and Maintenance
I always pay attention to how easy a baby product is to clean, and this cup felt manageable. I prefer items that do not create extra work, and this one fits that need fairly well. Since toddlers use cups often, I like that it is made for regular washing and everyday convenience. A cup that is easy to maintain saves me time and helps keep things hygienic.
Spill Resistance and Practicality
In my experience, no toddler cup is completely mess-free, but this one does a good job of minimizing spills compared to open cups. That gave me more confidence when my child was learning to drink independently. I found it practical for use at home, during travel, and even while sitting in a stroller or car seat for short periods.
Comfort and Grip
I noticed that the cup is designed with toddlers in mind, so it feels comfortable for small hands. My child was able to hold it without much struggle, which made drinking feel more natural. For me, that matters because a cup that is too bulky or awkward can discourage a toddler from using it consistently.
Who I Think This Cup Is Best For
I think this training cup is a good fit for parents who want a simple transition cup for toddlers. If you are looking for something that encourages independent drinking without jumping straight to a regular open cup, this is a solid option. I would especially consider it if you want a cup that balances ease of use, training support, and spill control.
My Final Buying Advice
If I were choosing a toddler training cup again, I would keep Dr. Brown’s Milestones Cheers 360 Training Cup on my shortlist. It offers a helpful middle step between bottles and open cups, and I like that it supports learning while reducing mess. For me, the biggest value is in how it makes my toddler feel more independent while giving me a little peace of mind.
Final Thoughts
I think Dr. Brown’s Milestones Cheers 360 Training Cup is a smart choice for toddlers who are learning to drink independently. My takeaway is that it offers a helpful balance of spill resistance, easy handling, and a design that supports the transition from bottle or sippy cup. Overall, I’d say it’s a practical option for parents looking for a simple, toddler-friendly training cup.
Author Profile
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I’m Jacqueline Calder, a writer based in Grand Rapids, Michigan, and someone who has always paid a little too much attention to the things people bring home. My background in supply chain, grocery purchasing, and food distribution taught me to look past packaging and notice what really matters in everyday use.
Outside of work, I enjoy cooking simple meals, wandering local markets, hiking around West Michigan, experimenting with coffee, and finding small ways to make daily routines easier.
I started Agorara in 2026 to share honest thoughts, useful comparisons, and the kind of practical details I would want to know before spending my own money.
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