Last month we took Kingston to New York City for his birthday. It was really just an excuse to visit the city during Christmas, but basically we’ve now insured that every birthday from here on out will be an epic disappointment. 🙂 It really was the perfect trip! You know how sometimes traveling with your family isn’t the best? (Just us?!?) Well, I’m thankful to report that this one turned out to be my favorite trip we’ve ever taken with King. He came alive when our plane landed and didn’t slow down the whole time. The highlight of the week was when we woke up one morning to the first snow of the season! It snowed hard all day, and Kingston was in Florida-kid heaven! Before our trip he had been asking us constantly if it was going to snow while we were in New York, so seeing his face when we walked out of our hotel that morning was the best thing ever!

If you’ve never been to NYC during Christmas, I can tell you this: there is something magical about the city in December. (And I never use the word “magical” in normal conversation – haha!) If you decide to go that month, expect to catch the Christmas spirit… BIG TIME. Even the worst Scrooge can’t help but get excited after a little taste of the big apple during the holidays. One of our favorite sights is the Winter Village at Bryant Park. They set up a ton of temporary shops, and there’s a beautiful ice skating rink and big Christmas tree. You can skate for free if you bring your own skates, so make sure to pack them. Ha! I like this area better than Rockefeller Center at Christmas. It isn’t usually as crowded, and there are places to sit and relax with “the best hot chocolate in the world” from No Chewing Aloud. It’s overpriced, and worth every penny. They put a truffle in each cup, so it’s rich and delicious! But of course, you must see THE TREE at Rockefeller Center. Go at night for the full effect and watch hundreds of people ice skating on the iconic rink. Also note that the wait to get onto that rink is usually several hours long. Yikes! Make sure you walk along 5th Avenue and take in all the shop windows. The displays are incredible and all so different. If you want to do a kid-friendly show, definitely check out The Radio City Christmas Spectacular! It’s a classic and fun for all ages. Take this from us though, avoid Santa Land at Macy’s at Herald Square. They started requiring appointments this year, so I thought, “Hey, we’re in NYC with King for the first time! We HAVE to see Santa at Macy’s. Everyone knows he’s the real Santa, and since they require appointments we won’t have to wait long.” Oh, I was wrong. WRONG! We waited in the longest line, and K didn’t really even care about seeing Santa. In fact, he told us that he knows Santa is fake and parents bring all the presents. So. You heard it here. Save yourself. 🙂 We definitely needed a pick-me-up at Doughnut Plant after all that! Then all was right with the world again.

I have to warn you that this post has a ton of pictures, but if you make it to the bottom I’ve included some tips for planning your own trip to New York City!

Are you ready to start planning now? Here are some ideas that I hope will help you!

Getting Around – Get a 7-day unlimited Metrocard for $32. You can choose to pay-per-ride, but if you’re going to use the subway a lot, (and you probably will) the 7-day card is cheaper. You can buy it from a kiosk inside any subway station. Get your money’s worth out of that card, and ride it everywhere! It will get you close to pretty much anything you want to do in the city. The subway can be tricky though. It’s our absolute favorite part about NYC (and King loved it so much), but if I didn’t travel with Anderson, the subway pro, it would be a lot harder to get around. We’ve tried all the subway apps over the years, and the biggest problem with all of them is that they don’t explain where/when you need to switch trains. They tell you which one to get on, but if you aren’t paying attention you’ll get turned around. The best apps we’ve found are KickMap NYC and City Mapper. There’s no phone reception in most of the stations, so the apps store the subway map on your phone for easy access. Anderson uses them the whole time we’re there to quickly get us around. But… know that if you’re traveling on the weekend the schedule completely changes. Good luck with that! People are really helpful, so don’t feel weird sticking your head in a train and asking, “Where is the next stop?” or “Is this an uptown or downtown train?” Keep a subway map handy, and give yourself extra time to get around. You can do it! And just FYI: If your kid is 44 inches tall or under, they ride for free. Just let them walk under the bars. If you don’t feel confident riding the subway you can always Uber, Lyft, or do something like a Hop On Hop Off bus. 

Booking a Hotel – When you’re planning a trip to New York, the hotel will probably be your biggest expense. Cheap flights are often available, but know that when flights are cheapest hotels are often pricier. Despite the expensive rooms, I still think it’s worth it to stay in Manhattan. Do some research and check deal sites. A lot of people focus on staying in Midtown, and it really is a great area as far as convenience, but don’t think that is your only option. Some of the other neighborhoods have so much character, and you can get anywhere by subway. For this trip we booked the Q&A Residential Hotel in the Financial District (downtown) through Travel Zoo. We’ve stayed in this area a few times now, and I always enjoy it. This time was no exception. The hotel was really nice and made up of big, apartment-style rooms with kitchens. It was one of my favorite places we’ve ever stayed in NYC. A few other hotels we’ve enjoyed were The Marriott Marquis in Times Square, The Tuscany, a boutique hotel near Grand Central and The New York Marriott Downtown – I booked this one using Priceline’s “Name Your Own Price” deal. Have you ever used that feature? It’s so nerve-racking, because you don’t know what hotel you’re bidding on! But I’ve done it several times and always had great experiences. Just make sure you only choose the hotel class you’re comfortable with (I never go lower than a 4 star!) and then choose the neighborhoods you want to stay in. Start picky then branch out to other neighborhoods if you can’t find anything for the price you want. There are thousands of hotels in New York City and finding a nice one for a good price can be hard, but just do your research and put in the time. It’s worth it!

Financial District (FIDI) –  A few highlights of this area are Wall Street, 911 Memorial, The Oculus, Freedom Tower, and The Battery. You can get a good look at Lady Liberty from The Battery or take the ferry over. But know that it will eat a big chunk of your day if you head over and wait in line to see her. We just like to salute her from lower Manhattan! Grab The Bull by the horns on Wall Street. I told Kingston it’s good luck to rub his balls, so he did! 🙂 The last time we went to the 911 Memorial it had just opened and you needed a pass to get in. Then you had to wait in a long line. But now it’s just an open park! You walk can just walk up anytime. If you want to pick up some groceries, check out City Acres Market on Pine Street. It’s like a smaller Whole Foods and has delicious prepared foods on the top floor and a full grocery store below. The subway service changes drastically in this area during the weekends when all the office buildings are closed. So it can be tricky to get around on Saturday and Sunday.

Midtown – You’ll probably spend a lot of time here! Top of the Rock has incredible views of the city that include the Empire State Building. Get your tickets online ahead of time! I really don’t like Times Square, but Anderson loves it. I do think it’s one of those things you should probably experience… once. Grand Central Terminal is beautiful! Get off the subway here and wander around. It’s breathtaking. Stand in the center and just turn in circles as you take it all in. Aside from the Main Concourse, there’s also a Dining Concourse with lots of food options and retail stores. Check out the whispering gallery right in front of the famous Oyster Bar and Restaurant. You whisper into one corner and someone else standing on the other side of the room can hear you. Kingston thought this was the coolest! The people watching is pretty good here too! Bryant Park is a fun spot even if it’s not Christmastime. And The Main Branch of the New York Public Library is right next to it!

Chelsea – Go to Chelsea Market and shop at Artists and Fleas then grab lunch or an afternoon snack/dessert and take it to the High Line and people watch while you eat. The High Line is a public park built on a historic rail line elevated above the streets on Manhattan’s West Side. And it’s another one of our favorite spots in the city. I could spend an entire afternoon up there!

Upper West Side – Wander through the UWS with no agenda – except maybe to grab a cookie from Levain Bakery. The dark chocolate chocolate chip is so good – and so rich that you can definitely share it. I love walking this area! Then hit Central Park – spend hours exploring. Get lost. It’s worth it. There’s so much to see and do! Also, the American Museum of Natural History is on the west side of the park and The Met and Guggenheim are on the east.

Brooklyn – Walk or ride a Citi Bike across the Brooklyn Bridge and eat at Grimaldi’s. It’s our favorite pizza in Brooklyn, and it’s cash only. Okay, it’s actually our fav pizza place in the city. We’ve tried a bunch of them and can’t find one that tops it! Then head to the Brooklyn Bridge Park or the Brooklyn Heights Promenade for an amazing view of lower Manhattan. It’s breathtaking at night! If it’s a weekend hit the Brooklyn Flea. If vintage shopping is your thing, Carroll Gardens and Williamsburg will not disappoint. Prospect Park is a gorgeous spot and totally worth a visit. It was designed by the same guys who did Central Park and is right next to Park Slope, an adorable Brooklyn neighborhood. There’s a great brunch place in Park Slope called Benchmark.

I hope all this info is useful if you’re planning a trip and need some help getting started! Check out this post next. It’s a list of some of our favorite family-friendly places to eat in NYC!

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