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10 Must-Dos for a Family-Friendly Holiday in NYC

I had seen all the pictures and heard all the stories of how magical a Christmas in New York City could be. Each year, I can literally feel the Christmas cheer coming through the television while watching the Macy’s Thanksgiving Day parade.

So, this year, with Mallory Grace, our daughter, on the edge of her 9th birthday, we decided we needed to experience it for ourselves. After all, she’ll be a tween before we know it.

And, by traveling the week before Thanksgiving, we ended up saving on hotel costs, crowds, and frigid cold temps! The timing couldn’t have been more perfect. We experienced the first snowfall of the season, the FAO Schwarz store reopening, the opening acts of the Rockettes, and the first peeks at all the NYC window displays—without the overwhelming crowds and overpriced accommodations.

Not to mention, we searched every city block for the most festive NYC sights and attractions that would still keep our daughter happily engaged. That being said, to leave you feeling inspired to book a trip to the Big Apple when the next holiday season rolls around, I’ve included our ten family favorites below along with some quick tips to make your stay even more memorable and stress-free.

1.  Statue of Liberty & Walk to the 9/11 Memorial

must-dos for a family-friendly holiday in nyc

The options for getting an up close and personal look at our Lady Liberty ranged from a free ride on the Staten Island Ferry to a four to five-hour round-trip tour of Ellis Island and the museum. We ended up opting for the one-hour round-trip ferry ride to both Ellis Island and Liberty Island where we stayed onboard the ferry. You can purchase tickets here and hop on at Battery Park.

The cozy indoor seating area, $2 hot cocoas, views out the windows served our family well and gave us plenty of extra time to walk up to the 9/11 Memorial afterwards. We felt it served as the perfect teaching moment to explain just how symbolic the Statue of Liberty really is.

must-dos for a family-friendly holiday in nyc

Tripbound Traveler Tip: It’s extremely easy to get conned by vendors at Battery Park claiming to offer tours. So, be sure to ONLY purchase tickets from the Statue Cruises booth located inside Battery Park, which is operated by the National Park Service. We narrowly escaped a run-in with a seedy operator ourselves who was charging double (cash only of course) for what would have become a bus ride to New Jersey followed by a disappointing run-down boat tour according to the 100+ unhappy reviewers online.

2.  Christmas Spectacular Starring the Radio City Rockettes

No trip to the city over the holiday season would be complete without seeing the Rockettes at Radio City Music Hall.

must-dos for a family-friendly holiday in nyc

Best of all, now, you can make it even more special by adding the Stage Door Tour for an additional $20 per person before the show. This 75-minute guided tour gives you a behind-the-scenes look at the design and creation of the center, photo op and Q+A session with a Rockette, peek into the costume room, and more.

It was money well spent and gave us an even greater appreciation for the production and its famous venue. For example, we learned that the beautiful crystal chandelier was a gift by Swarovski for the 75th Anniversary of the theatre!

3.  Ice Skating in Bryant Park & Strolling Through Winter Village

One of the best pieces of advice we got from the locals was to go ice skating at Bryant Park instead of Rockefeller Center. It costs less (it’s NYC’s only free admission rink!), and the crowds aren’t nearly as bad this time of year.

must-dos for a family-friendly holiday in nyc

Oh, and you can’t beat the outdoor holiday market at Bank of America’s Winter Village! It’s also located in Bryant Park, which is definitely an added bonus.

4.  Take a Horse-Drawn Carriage Ride in Central Park

For about $50 you can hop on one of those perfectly holiday-esque horse-drawn rides through Central Park. You’ll get to set your sights on well-known attractions like Belvedere Castle, the Lake, Strawberry Fields, Bethesda Fountain, and the Mall. Ours even came complete with warm fluffy blankets and newly fallen snow!

Tripbound Traveler Tip: Be wary of the very eager merchants selling these rides through the park. They are known to trick tourists into paying for a $5 per minute rickshaw ride vs. one of the beautiful carriages, which are half the price.

5.  Walk Down 5th Avenue & Check Out the Holiday Light Displays

Let’s face it. Shopping with kids in tow can be a major drag! Personally, I’ve never understood why anyone would ever want to take their kids shopping with them. But, window shopping in the city is a whole other thing altogether.

The windows are pure magic and something our entire family enjoyed. Our favorites were Bergdorf Goodman’s cotton candy and gingerbread-inspired windows, and Saks’ rainbow-colored displays!

must-dos for a family-friendly holiday in nyc

6.  Shop FAO Schwarz

Our trip to the city was perfectly timed with the reopening of FAO Schwarz’s famous toy store, which is complete with the piano floor made famous by Tom Hanks in the movie “BIG”.

must-dos for a family-friendly holiday in nyc

This place was also full of interactive experiences—from science experiments to magic tricks, and even Build-A-Bear experiences. It was the perfect chance to kick-off some holiday shopping and get some ideas for what to add to our wish list for Santa.

7.  Splurge On a Night at The Plaza

We tend to invest in experiences over gifts for Mallory Grace. She’s never really been interested in toys, and we love making memories together.

For that reason, we decided to do a night at The Plaza as a special pre-holiday Eloise-inspired treat for her. It was truly the fanciest place we’ve ever stayed. The furs and the fashion alone were out of this world!

must-dos for a family-friendly holiday in nyc

must-dos for a family-friendly holiday in nyc

must-dos for a family-friendly holiday in nyc

must-dos for a family-friendly holiday in nyc

But, we came for Eloise. MG loved the Eloise store, special Eloise breakfast at Palm Court, and bathtub big enough for a swim. The place just screams fancy, fancy, fancy holiday!

8.  Eat Chicken Wings at Carmine’s & Take In the Lights at Times Square

There’s something about the rosemary-scented scarpalio wings, Frank Sinatra playlist, and authentic Italian ambience at Carmine’s that is so quintessentially New York. It’s also perfectly located in Times Square, so it’s a great option for dinner before a Broadway show. Come hungry, though! The portions are huge and all served family-style.

Tripbound Traveler Tip: Make reservations early! This is one of the busiest restaurants in the Big Apple.

must-dos for a family-friendly holiday in nyc

9.  Have an Overpriced Lunch at the Stardust Diner

The Stardust Diner is a multi-level 50’s-style diner with aspiring Broadway singers disguised as waiters. It was a lot of fun for Mallory Grace, albeit a little loud and overpriced for Dad. Nonetheless, it certainly added to our overall NYC experience and the smile on MG’s face made the $25 hamburger well worth it.

must-dos for a family-friendly holiday in nyc

must-dos for a family-friendly holiday in nyc

must-dos for a family-friendly holiday in nyc

Tripbound Traveler Tip: Bring some extra cash for an optional tip to add to “Phil-up” the bucket. Each night, the money is shared among servers to be used only for singing and dancing lessons to help them make their way to Broadway.

10. Visit the Real Winnie-the-Pooh & Friends at the New York Public Library

The grandeur of the NY Public Library left us all in complete awe. But, no one more so than Mallory Grace who got to see the original Winnie-the-Pooh and his friends down in the children’s section. It’s also the perfect pit stop for warming up and slowing down when walking out in the crisp cold air of the city!

must-dos for a family-friendly holiday in nyc

must-dos for a family-friendly holiday in nyc


Wondering where to stay to enjoy all this fun & excitement?

Wyndham Midtown 45 at New York City offered the perfect location for our Big Apple adventure. It was walking distance to nearly everything we visited, including Grand Central Station, Bryant Park, Rockefeller Center, and Radio City.

must-dos for a family-friendly holiday in nyc

must-dos for a family-friendly holiday in nyc

must-dos for a family-friendly holiday in nyc

What’s even better? Tripbound offers suite-style stays at this chic, modern resort, complete with a mini-kitchen, separate bedrooms, and super spacious floor plans that were perfect for our family vacation. And, all at a super sweet deal!

So, what do you say? Are you ready to book this memory-making getaway today? Visit the resort’s page to get an instant quote or call now at 1-888-816-5214.

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