Travel
Travel

Our Sweet Cherry's First Big Adventure: Hawaii with a Newborn!

Okay you guys, Cherry's first trip to Hawaii was everything and more. I was a little nervous traveling with a newborn, ngl, but seeing her little face light up (or just sleep peacefully, hahah) made it all worth it. It felt like a dream, and I'm still pinching myself.

By Lo Beeston|February 12, 2026| 6 min read
Our Sweet Cherry's First Big Adventure: Hawaii with a Newborn!

Key Takeaways

- Traveling with a newborn isn't as scary as it sounds, just gotta plan a little! - Don't be afraid to ask for help, whether it's Tanner or family or even just a kind stranger. - Prioritize those sleepy snuggles and slow moments, bc that's where the real magic is. - Pack smart, but also remember you can buy things there if you forget! - Soak up every single second, they're only little once :,)

Our Sweet Cherry's First Big Adventure: Hawaii with a Newborn!

Hey my loves!! Okay, I'm still on cloud nine from our Hawaii trip, and honestly, I just wanted to sit down and share all the feels with you guys. Like, truly, it was such a special time, especially with our littlest love, Cherry, getting to experience it all for the very first time. I know I posted a little snippet on Instagram, but there's so much more to tell, and I feel like you guys are my besties, so here we go.

When we first started talking about this trip, I'm not gonna lie, I had a tiny little pit in my stomach. Traveling with a newborn? Like, what does that even look like? I remember thinking back to when Stella and Ozzy were little, and it felt like a whole different ballgame. But then I looked at Cherry, all tiny and perfect, and I just knew we had to do it. These moments, these firsts, they're so fleeting, and I didn't want to miss out on making these memories with her, with all of us as a family of five.

Tanner, bless his heart, is always my biggest cheerleader. He was like, "Lo, we got this! It's Hawaii!" And he was so right. Having him by my side, always ready to help with a diaper change or just hold Cherry so I could eat a hot meal (a luxury, am I right?!), made all the difference. He's seriously the best dad, and watching him with our girls just melts my heart every single time.

So, yeah, we packed our bags, probably overpacked, but idc, better safe than sorry, right? And we headed off for what turned out to be one of the most beautiful, relaxing, and memorable trips we've ever had. It was a Thanksgiving to remember, for sure. So grab a snack, get comfy, and let's chat about all things Hawaii with a newborn!

The Journey: Flying with a Tiny Human

Okay, let's talk about the flight first, bc that's usually the biggest hurdle, right? I was so nervous. I mean, what if she cries the whole time? What if she's uncomfortable? What if I forget something crucial? All those mom worries hit me hard. But honestly, it was smoother than I could have ever imagined. We booked a red-eye, which I think was key. Cherry slept for most of it, snuggled up close to me. I wore her in a carrier for boarding and deplaning, which made things so much easier than trying to juggle a car seat and bags and everything else. Plus, she loves being close to me, so it was a win-win.

We made sure to feed her during takeoff and landing to help with her ears, and she handled it like a champ. Stella and Ozzy were amazing, too, keeping themselves entertained with their tablets and snacks. It's wild how much they've grown and how independent they are now. I remember when they were the ones I was worried about on flights! Time truly flies, you guys. I just kept reminding myself to breathe and that we'd get there eventually. And we did! Safe and sound, and ready for some sunshine.

Settling In: Finding Our Rhythm in Paradise

Once we landed, it was like a wave of calm washed over me. The warm air, the palm trees, the smell of the ocean – it just instantly puts you in a good mood. We got to our place, and the first thing we did was just unpack a little and let everyone relax. With a newborn, you can't just hit the ground running, and honestly, I'm so glad we didn't. We took it slow.

Cherry spent a lot of time just sleeping in her bassinet or snuggled up in my arms while we sat on the lanai, listening to the waves. Those quiet moments were everything. I feel like sometimes we get so caught up in doing all the things on vacation, but with a baby, it forces you to slow down and just *be*. And honestly, it was such a gift. We had so many cuddles, so many sweet little moments of just watching her sleep, or seeing her tiny hands reach out. It's those simple things that fill your heart, you know?

Beach Days and Family Fun

Of course, we had to get to the beach! This was Cherry's first time seeing the ocean, and while she probably won't remember it, I will. We found a nice shady spot, set up our little beach tent for her, and just enjoyed the sand between our toes. Stella and Ozzy were in heaven, building sandcastles and splashing in the shallow water. Tanner was right there with them, throwing them around and making them laugh. It's moments like these that I just want to freeze forever.

For Cherry, it was mostly about staying cool and comfy. We kept her shaded, applied baby-safe sunscreen (after checking with her pediatrician, of course!), and made sure she was hydrated. We didn't stay for super long stretches, just an hour or two, enough for everyone to get their beach fix without overdoing it. It's all about balance, especially with little ones. And honestly, just being there, together, as a family, was the best part. Seeing Stella and Ozzy dote on their baby sister, pointing out the waves to her, it was just the sweetest thing :,)

Thanksgiving in Paradise: Counting Our Blessings

And then there was Thanksgiving. Oh my goodness. Being in Hawaii for Thanksgiving was so unique and special. We had a beautiful dinner, not a traditional one with all the fixings, but it was perfect for us. We talked about everything we were grateful for, and honestly, my heart was just overflowing. Sitting there, looking at Tanner, looking at Stella, Ozzy, and then down at little Cherry sleeping soundly in my arms, I just felt so incredibly blessed.

My mom, who raised me as a single mom, taught me so much about gratitude and making the most of every moment, no matter what. And I feel like she was with us in spirit, smiling down. This little family, this life we've built, it's more than I could have ever dreamed of. And having Cherry here, this new little addition, just completes us in a way I didn't even know was possible. She truly is an angel, and I'm so grateful for every single sleepy sigh and tiny stretch.

Tips for Traveling with a Newborn (from a very tired but happy mom!)

  • Pack Smart (but don't stress!): I brought way more diapers and wipes than I needed, but hey, peace of mind! Don't forget a lightweight stroller or carrier, a portable sound machine, and plenty of burp cloths. But also, remember you can buy things pretty much anywhere if you forget something!
  • Embrace the Slow Pace: This isn't the trip to cram in every activity. Let your baby set the schedule. Naps are sacred, and quiet moments are golden.
  • Ask for Help: Tanner was my rock, but don't be afraid to ask for help from family or even a kind flight attendant. Most people are so sweet and understanding when they see a new baby.
  • Stay Hydrated & Fed: For you and baby! Especially if you're breastfeeding, make sure you're drinking tons of water.
  • Baby Carrier is Your Best Friend: Seriously, hands-free is the way to go for airports, walks, and just generally keeping baby close and comfy.
  • Don't Forget the Sun Protection: For baby, that means shade, lightweight clothing, and baby-safe sunscreen where appropriate.
  • Capture the Moments: Take all the pictures and videos! Even if you feel like you look tired (which, let's be real, you probably are hahah), you'll cherish these memories forever.

So, yeah, that's a little peek into our Hawaii trip with Cherry. It was everything I hoped for and more. If you're thinking about traveling with a newborn, I say go for it! It might be a little different, a little slower, but the memories you make are absolutely priceless. And seeing the world through their brand new eyes, even if they're mostly closed, is just the best thing ever. Sending you all so much love! XOXO Lo