A December to Remember: Our Magical Holiday Weekend in New York City

There’s something undeniably enchanting about New York City in December. The air feels crisper, the lights twinkle brighter, and every corner seems dipped in a kind of cinematic holiday magic. This year, we decided to lean all the way in—festive outfits, iconic NYC experiences, and the kind of memory-making that feels both effortless and extraordinary. Here’s how our long weekend unfolded, moment by sparkling moment.

Day 1: Touchdown & Broadway Wonder

We touched down at JFK ready to dive into a weekend built around celebrating our birthday boy. By 3:00 PM, we had checked into our Hotel and had Balloons from Balloon Kings and Gluten Free and Vegan Pastries from Posh Pop Bakery.

Dinner at Estiatorio Milos felt like the perfect start: elegant, warm, and delicious. Their seafood is some of the freshest I have ever had with all on display.

Then came one of the highlights of the weekend: Harry Potter and the Cursed Child at the Lyric Theatre. We arrived by 8:00 PM, and from the very first moment, the show was pure magic. It was the ideal surprise—immersive, spectacular, and the kind of experience that stays with you long after the curtain falls. Tom Felton, who played Draco Malfoy in the original series, is starring in the show until May 2026 and he gets a huge applause every time he is on stage making for a very fun show!

Day 2: A Sunday Steeped in Classic New York

We began the day with a meaningful pause at St. Patrick’s Cathedral for Mass—a beautiful moment of gratitude and grounding for our family and our birthday boy.

Lunch at Tavern on the Green felt like stepping into a snow globe—Central Park sparkling outside the windows. Afterward, we ventured out for a carriage ride through Central Park, a whimsical and timeless birthday treat that made all of us feel like kids again.

By 6:00 PM, we were at Radio City for the Rockettes Christmas Spectacular—a show that delivers pure joy every single time. It was festive, dazzling, and such a fun way to celebrate.

We wrapped the evening at Nobu 57, with a dinner that was both sophisticated and cozy—just right for a December birthday night in Manhattan. This restaurant was chosen as we have a requirement that you have to try a new cuisine when on a solo trip!

Day 3: Wall Street, Lady Liberty & Pure Holiday Magic

This day was packed with bucket-list moments—each one chosen to make the birthday trip unforgettable.

We began with a visit to the New York Stock Exchange followed by the deeply moving 9/11 Memorial.

At 1:00 PM, we boarded the ferry for the Top of the Crown Experience at Liberty Island—an extraordinary moment of history and perspective. These tickets open up six months in advance, and I highly recommend it for a once in a lifetime experience. Fair warning though, if you have a fear of heights or are claustrophobic, this is not the activity for you as it’s a very narrow and steep staircase that leads you to the top.

Then came full holiday joy: our Rockefeller Center tree photo followed by VIP ice skating. Skating beneath the world’s most iconic Christmas tree on a birthday? Truly unforgettable. I highly recommend booking your photo experience in advance as there was no wait whatsoever and it was very manageable.

A quick stop at FAO Schwarz brought out the playful side of everyone—because no New York birthday trip is complete without a visit to the most magical toy store. The line in the early evening was only about 20 minutes long, which was much better than the 2 hours earlier in the day. The JellyCat Diner requires advanced reservations which are released 4 weeks in advance. Book you reservations here. Another new feature is the FAO-Abulous Boutique where girls can create their own dream makeup collection. This experience also requires advanced reservations which you can book here.

One of our family favorite restaurants for over 30 years is where we chose to have our final dinner in the city, Trattoria dell'Arte. This institution is more of a locals place than a place to see and be seen. What I love is that the food is delicious. the environment fun and on the louder side and we have always felt comfortable taking our children there for a lively and tasty meal.

And to be extra festive we ended the evening at Serendipity 3 for a dessert finale. Frozen Hot Chocolate made for a unique birthday treat! I think this is a one and done for us. but I can see why it is heralded as a fun activity.

Day 4: Tea, Shopping, & Santa

For our final birthday morning, we headed to The Palm Court at The Plaza for afternoon tea—elegant, charming, and the perfect celebratory touch.

Then came 5th Avenue shopping where the windows alone are a gift. We ended with a visit to the Top of the Rock to see Santa, adding one last burst of holiday magic to the trip. Highly recommend the Express Pass to bypass all of the lines and deliver the best views!

Celebrating our son’s birthday in New York City during the holidays felt like stepping into our very own festive fairytale. From Broadway to ice skating, from heartfelt moments to sparkly adventures, the weekend was everything I hoped it would be: meaningful, magical, and beautifully unforgettable. From the timeless traditions to the small, spontaneous moments in between, this trip gave us everything we hoped for and more. And yes… I’m already dreaming of taking the whole family back next year!

Download Itinerary Here