Without Overplanning Your Days
Planning a New York City holiday trip with kids can feel exciting… and completely overwhelming at the same time.
There’s so much to see, so much pressure to “do it all,” and only so many hours in the day—especially when you’re navigating naps, meltdowns, cold weather, and crowds. After planning our NYC holiday trip for nearly a year, here’s the biggest lesson I learned:
The magic isn’t in the schedule. It’s in the flexibility.
Why Overplanning Steals the Joy
When I first started planning, I had pages of notes, saved Instagram posts and blogs, and a long list of must-see holiday spots. And while research is helpful, trying to cram too much into each day can quickly turn magical moments into stressful ones.
Long lines, slow walks, unexpected illnesses, and tired kids will change your plans. That’s not failure—that’s real life.
The more rigid the agenda, the harder it is to enjoy what’s right in front of you.
Create a List — Not an Agenda
One of the best decisions we made was creating a list instead of a schedule.
Think of it as:
• A handful of top priorities
• A backup list for open pockets of time
• Permission to pivot when needed
Our rule of thumb:
One main activity per day.
If anything else happened, it was a bonus—not an expectation.
Booking Timeline: What to Reserve (and When)
Here’s a realistic planning timeline for NYC during the holidays:
• Hotels: Book 6+ months in advance for better availability and pricing
• Restaurants: Months ahead for popular or holiday-themed spots
• Activities: Ice skating, shows, and Santa experiences book fast—aim for 1–3 months out
Book the must-haves, and let the rest stay flexible.
Must-Dos vs Backups: How to Decide
Ask yourself:
• What experience would we be most disappointed to miss?
• What can we easily replace if plans fall apart?
For us, skating at Rockefeller Center and walking through the holiday lights mattered most. Everything else fit around our energy levels, weather, and mood.
Use a Custom Google Map (This Is a Game-Changer)
Create a Google Map with:
• Restaurants
• Attractions
• Cafes
• Shops
When you suddenly have extra time—or need to pivot—you’ll instantly know what’s nearby without scrambling or scrolling.
One Thing a Day Is Enough
NYC during the holidays moves slower than you think. Crowds are heavier, lines are longer, and walking with kids takes time.
Scheduling one main thing a day:
• Reduces stress
• Leaves room for naps and downtime
• Makes space for unexpected magic
Some of our favorite moments weren’t planned at all such as a really cold “Santa cart” ride (Santa pedaling a bike while we ride in the carriage).
Planning with Kids Means Planning for Flexibility
As my husband likes to joke, we survive all the chaos for about 10% of the memories—and somehow, those are the ones that last a lifetime.
Planning a NYC holiday trip with kids isn’t about controlling every detail. It’s about creating space for wonder, presence, and joy—even when things don’t go as planned.
Up Next in the Series
In the next post, I’ll share where we stayed in NYC during the holidays and why location (and accessibility) mattered more than anything for our family.
