We traveled to Portland, Maine the first weekend of December with a group of close friends and all of our kids, drawn north by one of those bucket-list holiday experiences that feels especially magical when your children are still young: The Polar Express Train Ride. My husband Dan and I made the trip with our three kids—Mila (6), Leo (3), and Eli (15 months)—at a stage of life where travel is less about checking boxes and more about finding places that can hold everyone comfortably.
The train ride itself delivered exactly what we hoped it would: wide-eyed wonder, Christmas music, hot cocoa and that quiet realization that these are the years you’ll want to remember later. But what surprised me most about the weekend was how much where we stayed shaped the entire experience. The right accommodations didn’t just give us a place to sleep—they gave us room to settle, to exhale, and to actually enjoy the trip without feeling like we were constantly managing logistics.
Instead of booking a traditional hotel, we stayed at the Docent Collection, and it turned out to be one of the best family travel decisions we’ve made—especially when traveling with multiple kids in the dead of winter.
Staying at the Docent Collection With Kids
The Docent Collection feels less like a hotel and more like being handed the keys to a beautifully designed city apartment—except with the ease, thoughtfulness and polish of a boutique stay. When you’re traveling with kids in December, that balance matters more than ever. You want warmth, space and flexibility, but you don’t want to give up walkability or feel removed from the energy of the city.
Our suite immediately felt livable. There was a full kitchen (a quiet lifesaver with kids), a dining area where we could sit down together, a spacious living room, a gorgeous bathroom and—most importantly—two full bedrooms. Mila and Leo shared one room, which felt exciting and special to them, while Dan and I had a bedroom to ourselves. That alone felt almost indulgent after years of travel where privacy is the first thing to go.
Eli slept in the living room in one of the Pack & Plays provided by the hotel, and somehow the setup worked seamlessly. No one felt displaced, no one was tiptoeing around each other and we all had space to wind down at the end of the day, which (when you’re wrangling winter coats, bedtime routines and overtired kids) makes an enormous difference.
Traveling with three kids often means someone is always sacrificing sleep, quiet or comfort. This setup eliminated that entirely. It felt calm, intentional, and genuinely family-friendly without ever feeling like a “family hotel.”
The Little Details That Made It Special
What truly set our stay apart, though, were the details—the kind you don’t always realize you need until someone gets them exactly right. That first morning, the staff delivered fresh croissants and donuts from a nearby local bakery, still warm and thoughtfully packaged. It was such a simple gesture, but it changed the rhythm of our mornings completely since we weren’t left having to do the usual scrambling, rushing, putting everyone’s jackets, hats and gloves on, etc. It was lovely to have a slow start with our coffees and our kids happily eating pastries in pajamas.
Even sweeter: each of our kids received a small lovie, which immediately became part of the weekend. Mila named hers before we even left the room. Leo carried his everywhere. Eli clutched his like it had always been his. All three came home with us, quiet reminders of a trip that felt personal rather than transactional.
When you’re traveling with young kids, those gestures matter more than luxury ever could. They made us feel welcomed, not merely accommodated—and there’s a big difference.
The Drive Up: A Festive Start
On the drive up, we stopped at Batson River Brewing & Distilling, which felt like the perfect first chapter of the weekend. The space was beautifully decorated for Christmas—twinkling lights, seasonal greenery, cozy corners that practically begged for a photo—and it immediately shifted us out of “travel mode” and into something softer and more celebratory. The kids ran around in their winter layers, cheeks pink from the cold, while the adults settled in with festive cocktails that felt especially earned after a long drive.
It was the kind of stop that works for everyone: relaxed enough for kids to be kids, but polished enough that the adults could linger, sip something fun, and actually catch up with friends. We took a handful of those in-between photos—the ones you don’t plan for but end up loving most—kids perched on stools, siblings bundled together, friends laughing mid-sip. The kind of pictures that instantly feel like memories while you’re still in them.
There’s something about easing into a trip like that—letting it unfold slowly instead of rushing straight to the destination—that changes the entire energy of the weekend. By the time we got back in the car and finished the drive to Portland, we already felt settled, connected, and very much on vacation.
Exploring Portland at Christmastime
One of the things that makes Portland such a wonderful destination with kids—especially in December—is how walkable and cozy it feels. The Old Port is filled with brick sidewalks, glowing shop windows, and that unmistakable New England winter charm that feels pulled from a holiday movie set.
We spent the day wandering without a strict agenda—popping into shops, warming up with snacks and drinks, letting the kids lead more than we usually do. Early December turned out to be the perfect time to visit: festive but not frantic, lively but not crowded.
That afternoon, we headed to The Polar Express Train Ride, which was, quite honestly, everything you hope it will be when you’re watching your kids experience it for the first time. From the moment we arrived, the entire experience felt intentionally designed for families—festive without being overwhelming, immersive without tipping into chaos.
Once onboard, the train transformed into a moving holiday scene: classic Christmas music playing softly, conductors in uniform moving through the cars, and hot cocoa served as the story unfolded. The kids were completely locked in—eyes wide, feet dangling, clutching their cups like it was all part of a very important ritual. Mila followed every moment with reverence, Leo reacted to each new surprise with pure delight, and even Eli seemed captivated by the lights, the motion, and the collective excitement humming through the car.
What made the experience especially enjoyable as parents was how well-paced everything felt. There was enough structure to keep the story moving, but plenty of space for kids to react in their own ways—talking, laughing, pointing things out, and fully participating without being told to sit still or stay quiet. It felt inclusive rather than performative, which is exactly what you want with young children.
By the time Santa made his appearance and the train ride came to an end, there was that rare, quiet moment where you realize you’re watching a core memory being formed in real time. If you’re visiting Portland with kids in December—or even planning a winter trip to Maine more broadly—this experience alone is reason enough to build a weekend around it.
A Final Morning Before Heading Home
Before packing up, we met friends at Bissell Brothers Brewing—and yes, it’s surprisingly great with kids. The space is large and open, the atmosphere is friendly and unpretentious, and it never once felt stressful to be there as a family. It’s the kind of place that reminds you Portland really does know how to blend food, community, and family life without making it feel forced.
Afterward, we spent the morning browsing Christmas shops around town, taking one last slow walk through the city before heading home—full, happy and already talking about when we could come back.
Final Thoughts: Portland, Maine at Christmas With Kids
This weekend was a 10/10, and staying at the Docent Collection played a huge role in that. When you’re traveling with kids—especially more than one—space, comfort and location matter more than anything else. Having room to spread out while staying right in the heart of Portland made the entire trip feel easier, calmer, and more memorable.
If you’re planning a family trip to Portland, Maine in December, I couldn’t recommend it more—and I wouldn’t hesitate to stay at the Docent Collection again.
We’d return in a heartbeat.
