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Our First Big Family Trip with Cherry: How We Survived (and Thrived!) on Vacation

Okay so I just got back from our first big family trip with baby Cherry and ngl, I was a little nervous. Traveling with three little ones, especially a newborn, felt like a whole new ballgame, but you guys, it was WAY better than I expected! I learned so much and wanted to share everything that made it actually fun and not just stressful.

By Lo Beeston|November 18, 2025| 6 min read
Our First Big Family Trip with Cherry: How We Survived (and Thrived!) on Vacation

Key Takeaways

- Embrace the chaos and lower your expectations, bc it's all part of the adventure! - Pack smart: less is more, but don't forget the essentials for each kiddo. - Snacks, entertainment, and a good carrier are your best friends for travel days. - Prioritize sleep for everyone, even if it means adjusting your plans a bit. - Remember to soak it all in and make those memories, bc they grow up so fast! :,)

Our First Big Family Trip with Cherry: How We Survived (and Thrived!) on Vacation

Okay, you guys. I just got back from our first big family trip with baby Cherry and ngl, I was a little nervous. Like, really nervous. Traveling with three little ones, especially a newborn, felt like a whole new ballgame. I mean, Stella and Ozzy are already a handful in the best way, but adding a tiny human who needs to eat every two seconds and sleeps in spurts? My brain was already calculating all the potential meltdowns, both theirs and mine hahah.

But you guys, it was WAY better than I expected! Seriously, I came home feeling refreshed and full of so many sweet memories, which honestly, I didn't think was possible with a newborn and two toddlers in tow. I learned so much on this trip, and I wanted to share everything that made it actually fun and not just stressful. Bc if I can do it, you can too! And if you're thinking about a family vacay but feeling overwhelmed, maybe this will give you a little push. Or at least some solidarity :,)

Lowering Expectations & Embracing the Chaos

This is probably the biggest lesson I learned, and honestly, it's a lesson I feel like I'm constantly relearning as a mom. Before we left, I had this vision of perfectly timed naps, peaceful dinners, and everyone smiling for every single photo. Hahahahah, yeah right. The reality was a lot messier, but also a lot more beautiful.

I went into this trip telling myself: "It's not going to be perfect. There will be meltdowns. Someone will probably poop at the most inconvenient time. And that's okay." And you know what? That mindset shift was everything. Instead of getting frustrated when things didn't go according to plan (which, let's be real, is like 90% of the time with kids), I just kinda rolled with it. When Stella refused to eat anything but bread for three days straight, I was like, "Okay, bread it is!" When Ozzy decided she needed to explore every single inch of the airport floor, I just let her. (Within reason, obvi!) And when Cherry needed to nurse right when we were about to walk out the door for dinner, I just sat down and fed her. Everything else could wait.

Tanner was such a champ, too. He's always my rock, but especially on trips like this. He just goes with the flow and reminds me to breathe and enjoy the moment. I'm so grateful for him. He's my hype man and my reality check all in one. ❤

Packing Smart (or at Least Smarter Than Me Usually)

Okay, packing. This is always my nemesis. I'm either overpacking like crazy or forgetting something crucial. For this trip, I tried to find a happy medium. My biggest tip? Think about each kid's essentials, not just general stuff.

  • For Cherry (the newborn): Diapers, wipes, burp cloths, a couple of swaddles, a few changes of clothes (bc blowouts are real, people), her sound machine (a lifesaver!), and a lightweight carrier. The carrier was clutch for airport walks and just keeping her close and comfy while we were out and about.
  • For Stella & Ozzy (the toddlers): Their favorite loveys, a few small toys that don't make a ton of noise (think quiet books, sticker pads, small figurines), their own water bottles, and a couple of outfits per day. I also packed a small backpack for each of them with their own snacks and a special 'travel toy' they hadn't seen before. That kept them occupied for a surprising amount of time!
  • For me & Tanner: Honestly, we packed way less for ourselves. Mostly comfy clothes, swimsuits, and our toiletries. We knew we'd be spending most of our time chasing kids, so fancy outfits were out the window hahah.

One thing I wish I had packed more of? Snacks! We brought some, but we ran out so fast. Kids are always hungry, especially when they're out of their routine. Lesson learned for next time!

Travel Day Survival Guide: Snacks, Screens, and Sanity

The actual travel days (flights, car rides) are usually what give me the most anxiety. But we actually crushed it this time! Here's what worked for us:

  • Snacks, snacks, snacks: I cannot stress this enough. Pack a ridiculous amount of snacks. Easy-to-eat things like fruit pouches, granola bars, crackers, dried fruit. Anything that keeps little mouths busy and happy.
  • Entertainment: For Stella and Ozzy, we definitely leaned into screen time a little more than usual. We downloaded their favorite shows and some kid-friendly games on tablets. No shame in that game when you're trying to survive a long flight! We also had those small, quiet toys I mentioned.
  • Baby carrier for the win: For Cherry, the carrier was a lifesaver. She slept in it through security, on the plane, and even while we were walking through the airport. It kept her cozy and close, and my hands were free for the other two.
  • Layers: Airports and planes can be super unpredictable with temperatures. Dressing everyone in layers meant we could easily adjust and keep everyone comfortable.
  • Wipes, wipes, and more wipes: Not just for diaper changes, but for sticky hands, spilled drinks, dirty surfaces. You can never have too many.

Tanner was amazing with the luggage and getting us through security. I swear he has a superpower for navigating busy airports. I just focused on keeping the girls happy and fed. Teamwork makes the dream work, right?

Prioritizing Sleep (for Everyone!)

Okay, this is a big one. When you're on vacation, it's tempting to push bedtimes and try to do all the things. But with little ones, especially a newborn, sleep is gold. We tried our best to stick to Cherry's feeding and nap schedule as much as possible, even if it meant one of us stayed back at the hotel with her while the others went to the pool for a bit. And for Stella and Ozzy, we tried to keep their bedtimes fairly consistent.

We also made sure to have a dark room for sleeping. We even brought a portable sound machine for Cherry, which really helped her feel like she was in her own space. When everyone gets enough sleep, it makes a huge difference in mood for the whole family. And honestly, a well-rested mom is a happy mom, and that makes for a much better vacation for everyone!

I remember one night, Cherry was just not settling, and I was so tired. Tanner just took her and walked around with her for an hour so I could get a little bit of sleep. He's seriously the best. I couldn't imagine doing this without him.

Making Memories & Soaking It All In

Beyond all the logistics and planning, the most important thing for me was just to be present and make memories. There were definitely moments of pure chaos – like when Stella decided to dump a whole bag of pretzels on the hotel room floor, or when Ozzy had a public meltdown bc she couldn't have another ice cream. But those moments are part of it, too. They're part of our story.

But then there were also these incredible, sweet moments: seeing Stella's face light up at the beach, Ozzy splashing in the pool with such joy, and Cherry just peacefully sleeping in her carrier while we explored a new place. Those are the moments I'll remember forever. Those are the moments that make all the planning and the occasional meltdowns worth it.

I love watching my girls experience new things. It's like seeing the world through their eyes, and everything feels new and exciting again. It's a reminder of how precious these years are and how fast they're growing up. :,)

So if you're on the fence about taking that family trip, I say go for it! It might not be perfect, and it might not be the most relaxing vacation you've ever had, but it will be an adventure. And you'll come home with stories, laughter, and a whole lot of love. And honestly, that's what it's all about, right?

I'm already dreaming about our next family adventure. Maybe a road trip? Or something even crazier? Idk, but I'm excited to find out! What are your best family travel tips? Let me know in the comments!