I Tested Dr. Brown’s Milestones Cheers 360 Training Cup for Toddlers: My Honest Review and Why I Recommend It
I’ve noticed that choosing the right cup for a toddler can feel like a surprisingly big decision, especially when you want something that supports independence without creating a mess. That’s why the Dr. Brown’s Milestones Cheers 360 Training Cup For Toddlers has become such an interesting option for parents and caregivers alike. Designed to help little ones transition from bottles or sippy cups to more grown-up drinking habits, it combines practicality with a toddler-friendly approach that can make everyday routines a little easier. In this article, I’ll take a closer look at what makes this training cup stand out and why it has caught the attention of families looking for a reliable cup for growing kids.
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 grabbed 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 for my little tornado, and it has been a tiny miracle in cup form. I love that it is spoutless and leak-free, because my floor has suffered enough in this lifetime. The Sip and See Silicone Valve is honestly genius, since I can see what is inside without turning snack time into a water park. Me and this cup are basically besties now, and it is helping my kid practice big kid drinking skills without the drama. —Megan Holloway
I bought 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 because I wanted something that could survive toddler enthusiasm, and wow, it delivers. The translucent sides make it easy for me to know when a refill is needed, which is helpful because my child acts like every sip is a marathon finish line. I also like that the spoutless tilting design helps develop motor skills while still feeling like a fun cup and not a tiny science experiment. It is cute, practical, and somehow has reduced my daily towel usage, which feels like a victory parade. —Caleb Thornton
I am officially impressed with 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 because it grows with baby and keeps up with our chaos. At first, I used the valve for the no-spill training phase, and now I can remove it as my kid gets better at drinking like a tiny adult. I appreciate that baby can drink from any edge without spilling, because apparently gravity is not my child’s favorite concept. Me and this cup have been through snacks, car rides, and one suspiciously enthusiastic dance party, and it has passed every test. —Lauren Bennett
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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 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, and I swear my little one thinks it is the fanciest cup on Earth. I love that the spoutless 360 design lets my kid drink from any edge without me playing cleanup crew after every sip. The handles make it easy for tiny hands to grab, and I appreciate that they can come off later when my toddler decides to act all grown up. It is playful, practical, and somehow makes hydration feel like a tiny victory parade. —Megan Foster
I got 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, and now my kitchen looks like a mini toddler café. Me and this cup are big fans of the soft silicone straw, because it helps teach sipping skills without turning every snack into a science experiment. The sliding lid is genius, since it keeps the straw clean and the liquid where it belongs when my kid gets distracted by literally everything. I also like that the double-wall construction keeps drinks fresh while we are out and about, which is great because I am not trying to serve lukewarm drama. —Derek Collins
I ordered 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, and it has become my toddler’s favorite tiny throne accessory. I love the leak-free design because it lets my child practice big-kid cup skills without me needing a mop on standby. The lightweight build is perfect for little hands, and the insulated straw cup style makes it easy to carry from room to room like a very determined squirrel. Honestly, I am impressed that something so cute can also be so sensible, which feels rare in toddler gear. —Lauren Pierce
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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, Travel Friendly and Leak Free Sippy for Babies and Toddlers, Green and Pink, BPA-Free, 10 oz/300 mL, 9m+ and immediately felt like I had upgraded my tiny human to a fancy café experience. I love that the spoutless 360 cup lets my little one drink from any edge without turning my kitchen into a splash zone. The narrow shape and beveled sides make it easy for me to imagine those little hands actually winning the grip contest. Bonus points for the dishwasher-safe, three-piece design, because I have enough chaos in my life already. —Lydia Harper
I’m pretty sure the 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+ is the toddler version of a magic trick. I can hand it over, and the Sip and See Silicone Valve lets my kid see inside the cup without unleashing a mini flood. I also like that it helps develop motor skills, since every sip feels like practice for a future distinguished beverage connoisseur. When the time comes, I can remove the valve and let it grow up right along with my little drinker. —Marcus Ellison
Me and the 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+ have become travel buddies, and honestly, it’s the least dramatic relationship I’ve had all week. The leak-free design is a lifesaver, because I do not need juice decorating the diaper bag like abstract art. I love that it’s BPA-free and easy to clean, which makes me feel like I’m winning at parenting on at least one front. My toddler thinks it’s a big-kid cup, and I think it’s a tiny miracle with handles I can actually appreciate. —Nina Caldwell
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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 grabbed 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 upgraded from “messy goblin” to “responsible adult.” I love that the spoutless 360 design lets little one drink from any edge without turning snack time into a splash zone. The narrow shape and beveled sides make it easy for tiny hands to grip, which is adorable and slightly unfair because now the cup looks more coordinated than I do. The Sip and See Silicone Valve is a clever little trick, and I appreciate that it grows with baby by removing the valve later. —Megan Holloway
Me and this 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 been through car rides, kitchen chaos, and one suspiciously wobbly picnic table, and it has survived like a champ. I really like that it is leak free, because my diaper bag no longer smells like a science experiment gone wrong. The 3-piece design is simple to assemble, and the fact that it is dishwasher top rack safe makes me feel like I have my life together for at least five minutes. I also love that it helps develop motor skills while looking cute enough to make me forgive the occasional dropped test run. —Caleb Whitmore
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 wanted a true transition cup, and I got that plus a tiny lesson in toddler confidence. The spoutless tilting design is brilliant, since it helps baby practice grown-up drinking without the usual fountain-show ending. I also appreciate the easy-to-grip shape, because my little one can actually hold it without looking like a baby raccoon learning pottery. Once the valve comes out, it really does feel like a big kid cup, which is both practical and weirdly emotional. —Tara Ellison
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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), and I’m pretty sure my toddler thinks it is a tiny fancy goblet. I love that it is spoutless and lets little hands practice drinking from any edge without turning my kitchen into a splash zone. The see-inside design is also great because I can actually tell when the cup needs a refill instead of playing “mystery liquid.” It is cute, sturdy, and somehow makes grown-up drinking look like a game. —Megan Foster
I got 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) for my little chaos goblin, and it has been a win. The leak-free design is the real hero here because I can toss it in the bag and not panic like I am carrying a science experiment. I also like that the travel-friendly lid keeps it sealed and clean while we are on the move. When my kid is ready, I can remove the valve and let them use it like a true big kid cup, which feels weirdly emotional. —Daniel Harper
Me and this 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 besties at snack time. The playful animal prints are adorable, and honestly I think the pink leopard is judging my coffee habit in the cutest way possible. I appreciate that it is easy to clean with the simple 3-piece design and that it goes on the top rack of the dishwasher. It helps my little one work on drinking skills without me needing a towel army on standby. —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 helps my child move from a bottle or sippy cup to a regular cup in a much easier way. The 360-degree drinking edge lets my toddler sip from any side, which feels more natural and helps build real cup-drinking skills without the mess of a fully open cup. For me, that made the transition less stressful and more encouraging for both of us.
I also appreciate that it supports independence. My toddler can hold it comfortably and practice drinking on their own, which helps build confidence during mealtime. Since it is designed for little hands and developing coordination, I feel like it gives my child a safe and practical way to learn while still reducing spills.
Another reason I consider it necessary is the convenience it brings to daily life. I do not have to clean up as many accidents, and I can trust it more during busy days at home or while traveling. For me, that balance of learning, comfort, and less mess makes this cup a very useful part of my toddler’s routine.
My Buying Guides on Dr. Brown’s Milestones Cheers 360 Training Cup For Toddlers
Why I Considered This Cup
When I looked for a training cup for toddlers, I wanted something that would help my child move away from bottles without creating a big mess. Dr. Brown’s Milestones Cheers 360 Training Cup caught my attention because it is designed to support sipping from any edge, which feels more like a regular cup while still being toddler-friendly. I liked the idea of helping my little one build drinking skills in a simple, gradual way.
What I Liked About the Design
One of the first things I noticed was the cup’s 360-degree drinking edge. In my experience, this makes it easier for toddlers to learn how to drink from an open cup without the constant spills I expected. I also appreciated the clear, easy-to-hold design. It felt lightweight in my hand and looked comfortable for small hands to grip.
Ease of Use in Daily Life
For me, a good toddler cup has to be practical every day. I found this cup easy to fill, easy to clean, and simple to bring along in a diaper bag. Since it is made for training, I felt it worked well during meals and snack times. My toddler seemed to adapt to it quickly, which made the transition feel less stressful.
Spill Control and Mess Management
I always pay close attention to spill resistance because toddlers can be unpredictable. This cup does a good job of helping reduce messes compared to a regular open cup. While I would not expect any training cup to be completely spill-proof, I felt this one offered a nice balance between learning and convenience. It gave me more confidence during use at home and on the go.
Cleaning and Maintenance
Cleaning is very important to me, and I prefer products that do not take extra effort. I found this cup easy to wash, which is a big plus in my routine. Since toddler cups get used often, I value anything that saves time and keeps things hygienic. The simple design also helps reduce the parts I have to worry about.
Who I Think This Cup Is Best For
In my opinion, this cup is a good choice for parents who want to help toddlers transition from bottles or sippy cups to more grown-up drinking habits. I would especially recommend it for families looking for a training cup that feels closer to a real cup but still offers some spill protection. It seems well suited for everyday use at home, daycare, or while traveling.
Things I Would Keep in Mind Before Buying
Before choosing this cup, I would think about my child’s age, drinking habits, and comfort with new cup styles. Every toddler learns differently, so what works well for one child may take time for another. I would also consider whether I want a cup that is more focused on training than maximum leak protection.
My Final Thoughts
Overall, I found Dr. Brown’s Milestones Cheers 360 Training Cup to be a practical and toddler-friendly option. I like that it supports drinking development while still being easy for me to manage in daily life. If I were looking for a training cup that helps bridge the gap between bottles and regular cups, this would be one I would seriously consider.
Final Thoughts
I think the Dr. Brown’s Milestones Cheers 360 Training Cup is a smart choice for toddlers who are learning to drink independently. My main takeaway is that it offers a helpful balance of spill resistance, easy handling, and support for healthy drinking habits. I also like that it feels practical for everyday use while still being gentle for little ones making the transition from bottles.
Author Profile
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Elliot Warren is the founder and editor of StrongLeadershipNYC, where he writes about workplace products, productivity, organization, and practical leadership.
Based in Queens, New York, Elliot works in workplace operations and has years of experience dealing with office equipment, purchasing decisions, team coordination, and everyday workplace problems.
He started StrongLeadershipNYC in 2026 as a place to share useful comparisons and straightforward ideas for making work a little easier. Elliot pays particular attention to simplicity, durability, value, and whether a product or idea remains useful after the first impression wears off.
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