Hey Chaos Planners! It’s your favorite mom-mess back again, ready to dish on the trials and triumphs of wrangling five wild and wonderful boys (aged 2 to 11) through a whopping 17-day winter break. Let me tell you, keeping this crew entertained and engaged for nearly three weeks straight is no small feat. But hey, that’s what us Chaos Planners live for, right?
Now, I’ll be honest, the prospect of filling 17 days with nonstop boy-approved activities had me feeling a tad overwhelmed at first. We’re a family that thrives on adventure – we love getting outside, exploring new places, and burning off endless energy. But the challenge lies in finding activities that resonate with everyone.
Thankfully, we have a secret weapon in our arsenal: Papi! This amazing partner-in-crime is the ultimate hype man, always up for an adventure and keeping the boys moving. So, armed with a healthy dose of creativity, a sprinkle of family time magic, and a whole lot of Papi’s enthusiasm, we embarked on a winter break extravaganza!
A Maine Event: Reconnecting with Family
First up on the agenda was a trip north to reconnect with family we hadn’t seen since July. The boys absolutely love spending time with their grandparents – Grampa’s sprawling snow-covered yard became their personal winter wonderland. Picture snowball fights that lasted until well after dark, epic sledding adventures down homemade ramps, and enough snow angels (ok, more like body impressions from impromptu wrestling matches) to blanket the entire property. It was pure, unadulterated fun, and the look of joy on their faces was priceless… from my cozy spot inside by the window with my nice, hot coffee!
Grampa’s house wasn’t the only place where family love filled the air. Mimi made many stops at most of our activities, and we were lucky enough to share multiple meals with a wonderful mix of great-grandparents, cousins, and friends. These moments of connection, of sharing stories and laughter around the table, are the heart and soul of what makes the holidays special for our family.
Bowling, Skating, and Snowy Hikes: Adventures Aplenty
Of course, no winter break would be complete without some classic family fun. We hit the lanes for a rollicking bowling session, the boys (and let’s be honest, Papi and I too!) reveled in the retro vibes of roller skating, and we even managed to squeeze in a snowy hike along the snowmobile trail behind Grampa’s house. The crisp air, the crunch of snow underfoot, and the camaraderie of exploring together created memories that will last a lifetime.
Home for the Holidays: Quiet Time and New Beginnings
As much as we reveled in our adventures, there’s something truly special about a “quiet” Christmas morning at home. Just the seven of us, surrounded by the remnants of wrapping paper and basking in the joy of new toys. It was a beautiful reminder that amidst the hustle and bustle, the true magic of the season lies in togetherness.
Finding Balance: Work, Play, and Everything in Between
Now, let’s talk about the reality of being an entrepreneur mom. Don’t get me wrong, I wouldn’t trade the chaos for the world, but there are times when running a business feels like a never-ending juggling act. As winter break wound down, we knew it was time to strategically re-introduce some structure back into our lives.
Did we feel a twinge of guilt about sending Jack back to daycare a few days early? Absolutely. But we also knew it was the right decision for our family. It allowed Papi and me to catch up on some work and ensure our businesses were prepped for the new year. In the meantime, the boys continued their adventures – some spending time with family, while others enjoyed their time in Jiu Jitsu day camps (because let’s face it, these boys have boundless energy!).
The Best Winter Break Ever: A Retrospective
Looking back, this winter break was a resounding success. It wasn’t about having every single minute meticulously planned; it was about creating a balance between family time, exploration, and allowing ourselves the space to breathe. We squeezed in epic adventures, reconnected with loved ones, and reveled in the simple joy of being together. Sure, there were moments of mess and mayhem (because let’s be real, that’s what comes with the territory!), but those are the moments that weave the fabric of our family memories.
So, to all my fellow Chaos Planners out there, embrace the whirlwind! Embrace the dance between adventure and downtime, between work and family. Because at the end of the day, it’s about creating a tapestry of experiences that nourish your souls and strengthen your bonds.
Here are a few key takeaways from our winter break adventures:

- Plan, but be flexible: Have a loose itinerary, but be prepared to pivot based on the kids’ moods and the weather. Sometimes the best adventures are the unplanned ones!
- Involve the kids: Let them help plan some of the activities. This gives them a sense of ownership and makes them more excited to participate.
- Embrace the chaos: Don’t strive for perfection. Let the kids get messy, let the house get a little crazy. These are the memories they will cherish.
- Prioritize family time: Schedule dedicated time for just the immediate family, whether it’s reading stories by the fire or playing board games, those quiet moments are packed with quality bonding time.
- Don’t be afraid to ask for help: Whether it’s grandparents, friends, or a trusted babysitter, don’t hesitate to enlist help when you need it.
- Remember to recharge: As entrepreneurs, it’s easy to get caught up in the hustle. Make sure to carve out time for yourself to recharge and rejuvenate.
This winter break was a reminder that even amidst the chaos, there is always room for joy, laughter, and unforgettable memories. And that, my friends, is what it’s all about.
What were some of your favorite family activities during the winter break? Share your tips and tricks for surviving the holiday season with kids in the comments below!
