What we did and what we skipped.
If you’re looking for a perfectly polished, do-it-all New York City holiday itinerary… this isn’t it.
What you will find here is a real-life, flexible NYC holiday itinerary with kids—built around naps, energy levels, weather, crowds, accidents, and a whole lot of grace.
This itinerary is meant to inspire, not dictate. Think of it as a starting point you can customize for your own family, travel style, and priorities.
Before We Begin: A Few Ground Rules
Before I walk you through our days, here are a few expectations I want to set—especially if you’re traveling with young kids:
- Walks will be slower
- Lines will be longer
- You will not do everything
- Bedtime routines will be flexible (or nonexistent)
And that’s okay.
Set your expectations low, leave room for rest, and focus on the moments that bring your kids joy—not the boxes you didn’t check.
Arrival Day: Ease Into the Magic
Because of our late arrival, we kept expectations very low.
- Third-party transportation from the airport (worth every penny with car seats and luggage)
- Check-in and quick unpack
- Evening stroll through Bryant Park Winter Village
- Hot chocolate from Cocoa Cabin (one of the best we’ve ever had)
Nothing fancy. Just soaking in the lights and the excitement of being there.
Day 1: Rockefeller Magic + Ice Skating Dreams
This was the day tied to my childhood dream—skating under the Rockefeller tree.
- Sleep in (as much as kids allow)
- Bundle up, layers on layers
- Ice skating at Rockefeller Center in the morning (lower crowds and pricing)
- Lunch at Luke’s Lobster under Rockefeller Plaza
- Quick stop at American Girl (Hot Wheels were the real win)
- Back to the hotel for rest, naps, and downtime
That evening:
- Babysitting help from a family friend
- Casual window shopping (crowded but fun)
- Late dinner at Sugar Factory (fun vibes, average food—set expectations accordingly)
Takeaway: Morning activities + afternoon rest = happier evenings.
Day 2: Snow, Flexibility, and Letting Plans Go
This became our biggest flex day—and one of our favorites.
- Woke up to New York City’s first snow
- Lego Store visit shortly after opening (manageable wait with kids)
- Exploring the city in the snow
- Stop at the New York Public Library to visit Patience and Fortitude
- Brunch at Heritage Grand Restaurant & Pizza Bar (arrived just before the rush)
Afternoon:
- Hotel downtime, Lego play, naps
Evening:
- Night walk to see holiday lights and window displays
- Dinner at CHILI (great food, relaxed vibes)
- Santa Cart ride to Hudson Yards (cold but memorable)
- Plans shifted: mall closed, High Line (an old above subway rail transformed into a mile long greenway and walkway) icy
- Cab ride back to the hotel
Takeaway: Some of our best memories came from plans that changed.
Day 3: Sick Kid + Divide and Conquer
This was the day that reminded us why flexibility matters most.
- One sick kid = mom and dad divide and conquer
- Dad and big brother explored while little brother rested
- Two-hour nap worked wonders
Later:
- Brunch at Le Pain Quotidien (fast, easy, kid-friendly)
- Attempted Macy’s Santaland even with reservations (lines too long—skipped)
- Holiday Lane on the 9th floor instead
- Picked out an ornament at Macy’s Holiday Square Market
Evening:
- No nap, quiet rest with a movie
- Dyker Heights & DUMBO holiday lights tour with My Christmas in New York
Absolutely freezing—but worth every shiver.
Departure Day: Early Morning Magic
Our final morning surprised us in the best way.
- 4:30am wake-up for mom and big brother
- Quiet city walks before the crowds
- Rockefeller tree lights turning on at 5am (missed by seconds—and still magical)
- Captured photos for a newly engaged couple
- Bakery date at Paris Baguette in Times Square (the only bakery opened closed by at 5:30am)
Later that morning:
- One last attempt at FAO Schwarz (success!)
- Late checkout at 1pm
- Smooth car service ride to the airport
Takeaway: Early mornings can be exhausting—but incredibly special.
What We’d Do Again (and What We’d Skip)
Would repeat:
- Morning activities
- Central hotel location
- Building in rest time
- One main activity per day
Would skip or adjust:
- Overly hyped restaurants
- Evening stroller use in heavy crowds
- Trying to squeeze in “just one more thing”
Final Thoughts
This itinerary worked because it wasn’t rigid. It gave us room to pivot, rest, laugh through the chaos, and soak in the magic with our kids.
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.
Up next in the series, I’ll break down where to save vs splurge on a NYC holiday trip, so you can plan with confidence and intention.
👉 Want my full NYC holiday list with saved spots and planning tips? Download it here and start dreaming—just remember to leave room for flexibility.
