I’ve been dreaming about this trip for as long as I can remember. New York is my favorite city in the world, and I put “experiencing all the seasons in New York City” on my bucket list way back as a teenager. We already spent 5 days there back in April 2016, so it was time for a fall/winter trip in 2018, also coinciding with my 25th birthday. So following a week of family time in Nebraska that included a Thanksgiving feast, a double birthday and my sister’s baby shower, we headed to the airport and flew to NYC.
We spent 5 days in the city between November 26 and December 1, so I hope the following itinerary will help you if you are planning your trip around this time of the year!
Two side-notes before we start off:
1) There are only a few truly Christmas-related items on this list, you can enjoy most of these activities any time of the year, really.
2) This itinerary can also serve as a “NYC guide for second-timers”, but if you’re going for the first time ever, I’d recommend reading my first blogpost on our 2016 trip: A WAY TOO DETAILED ITINERARY FOR NYC FIRST-TIMERS
Without further ado, let’s see what we did during our 5 days in NYC:
Day 0: Arrival
After landing at LaGuardia Airport, we took a cab to Bedford-Stuyvesant, Brooklyn, where we camped in an amazing Airbnb for the first few days that I can’t recommend enough! We opted for Brooklyn again because, first of all, it’s still cheaper than any Airbnb in Manhattan, and secondly, we wanted to explore some areas there we didn’t have time for during our first visit. Even if you want to spend most of your time in Manhattan, the subway will take you to the World Trade Center in half an hour.
As we arrived in the afternoon, we didn’t really plan anything for that day. We would have probably gone for a walk had the weather been nicer, but we were welcomed by a rainstorm, so we decided to start off our week by going to the movies. As we learned it’s definitely not recommended if you’re on a tight budget, but for this one time we had a blast at AMC Village watching Dr. Seuss’s The Grinch! As the Strand Book Store was just around the corner, we paid a visit after the movie to buy a copy of the just-then-published memoir of Michelle Obama. It’s one of my favorite bookstores in the world anyway, so we got lost there for the night!
Day 1: Brooklyn Heights, DUMBO & the World Trade Center
There’s no trip to NYC without a visit to the Brooklyn Bridge, if you ask me! It’s also a good base if you’re planning to spend your day in Brooklyn Heights or DUMBO. We stayed on the Brooklyn side of the bridge this time, followed by an almost aimless walk through Brooklyn Heights.
Some streets and places we loved (and which also provided for great photo ops):
- Cranberry St
- Willow St
- Columbia Heights
- Brooklyn Heights Promenade (our favorite!)
- Hicks St
- Cadman Plaza Park
- The Granite Prospect/Pier 1 (panoramic viewpoint)
Following our morning stroll, we headed back to Brooklyn Bridge and continued our walk in DUMBO. We didn’t wander far from the bridge though, as we started to get hungry and had our eyes on Grimaldi’s Pizzeria.
The highlights of our DUMBO walk included:
- Jacques Torres (chocolate chip cookies as big as my head) and One Girl Cookies on Water St
- the iconic Manhattan Bridge shot with the Empire State Building in the background (Water St)
- Main Street Park / Pebble Beach
- Jane’s Carousel / Empire Fulton Ferry Park
And finally: Grimaldi’s Pizzeria. Need I say more?
We said goodbye to Brooklyn in the afternoon and took the subway to the World Trade Center. Last time we skipped the Oculus, so now we checked out its interior, and then headed to the Century 21 on Dey St to do some birthday shopping. This is totally optional, of course, and I’d recommend walking around the area and visiting the 9/11 Memorial instead if it’s your first time in NYC!
Day 2: Midtown Manhattan
For us, this day started with packing and trading our Airbnb apartment in Brooklyn for another in Midtown Manhattan. This was our first time staying in Manhattan, and I have to admit it had its perks as we could walk to most of the sights we wanted to see.
After settling down, we started our walking tour in Bryant Park, one of my favorites in town. (If I had to choose my top three parks in NYC, they would be: Bryant Park, Central Park and Prospect Park!) Last time we only enjoyed the waffles at Wafels&Dinges and took our time sitting on the green chairs, but this time of the year Bryant Park also hosted the Winter Village, full of holiday shops, hot apple cider and an ice rink. If you’re there when the shops are open, I would recommend checking out the awesome pouches of Pamela Barsky, the holiday outpost of Strand Book Store (yes, that again, sorrynotsorry) and the Paintings by Yvoni booth for beautiful NYC paintings by a local artist.
After sipping up all the apple cider while watching the ice skaters for what felt like hours, we headed to the New York Public Library, where we not only got to visit the Rose Main Reading Room that was under renovation last time, but also discovered that the actual plush animals that inspired Winnie the Pooh are on display here, and after watching Christopher Robin during our inbound flight, it was especially heartwarming to see them all in real life.
Now what followed our library tour – and a quick detour to the Barnes and Noble on 5th Ave that resulted in a signed copy of Reese Witherspoon’s book Whiskey in a Teacup – was the whole reason we planned our trip around November 28: seeing the Rockerfeller Center Chrtismas Tree Lighting in real life! This has been my number one travel bucket list item of all-time, and I couldn’t believe my luck when I was finally on the streets trying to save a good spot for the ceremony.
Trying, I say, because even an hour before it began, the streets were full of a tremendous amount of people, the police already cordoned off most of the area surrounding the Rockerfeller Center, and the closest we got was almost a block away. So we were there, totally stunned, even though I heard you should be there 3-4 hours in advance, but I was like no way! Guys, let me tell you, this time it’s really true!
We couldn’t see a thing and barely heard the singers who performed at the tree, so we decided to go home – luckily just a few blocks away – and watched the whole show online. Actually, it was still magical because I knew I was really there and I saw the tree before it was all lit up and I also saw it the day after in full Christmas decor, and that’s something that nobody can take away from me. Even now, I get goosebumps when I hear Rob Thomas sing Merry New York Christmas on the radio!
Day 3: SoHo, Lower East Side, Greenwich Village & a Broadway Show
Brace yourselves, it’s gonna be a long day!
We started off in SoHo to do some shopping at the Amazon store, but our morning walk included a lot more than that:
- wandering around SoHo and admiring the industrial architecture
- visiting Housing Works Bookstore Cafe & Bar and buying a copy of Beatrix Potter’s The Tale of Peter Rabbit (yes, I came home with about a dozen books from this trip)
- wandering around the Lower East Side and admiring the architecture
- visiting Bluestockings Bookstore, Cafe & Activist Center (and buying more books)
- re-visiting Yonah Schimmel’s Knish after 3 years and buying all the knish in the world before realizing we also wanted to visit Katz’s Deli
- visiting Katz’s Deli for the first time and buying a pastrami sandwich to share – realizing it’s way too much after all the knish we ate, but finishing it anyway because it’s just the most delicious food in the world
Then we were off to the Village Party Store in Greenwich Village. Why, you might ask? Because my other bucket list item for this trip was a birthday photo shoot walking around the Village with a 25 balloon. What followed was an epic fail, nonetheless memorable for a lifetime. The guy at the store told us the balloons might lose their shape a bit outside due to the cold, but they definitely weren’t ready for the wind. So we lost balloon 2 even before we reached our ideal photo shoot spot, and had to do the whole thing with balloon 5, ending its miserably short life with a straw about 15 minutes later. Neverthless, we had fun!
After a spending some more time in Greenwich Village (visiting Washington Square Park, Bleecker Street, the Friends Apartment, and bookbook, a really cool book store that has since closed permanently), we headed back home before the most spontaneous program of our trip: a Broadway show. I never really felt the urge that I just had to see one in my life, but on our first day in back in Brooklyn I learned two things:
- They started playing The Lifespan of a Fact starring Daniel Radcliffe at Studio 54 just a month before
- You can buy cheap tickets at todaytix.com
The fact that I could see the actor who played a huge role in my pre-teen and teenage years as the one portraying Harry Potter, and the fact that I actually like Daniel the actor himself, was more than enough to rush to to website and buy those tickets – for just $59 each! If you cannot guess already, I was in tears from the moment I saw him, and the play itself was amazing – it’s a shame they only had it on for 16 weeks.
Day 4: Central Park & Columbia University
Oh, Central Park. Definitely one of my happy places in New York – I even have a separate bucket list dedicated to activities to do there. Aside from watching the Rockefeller Center Christmas Tree Lighting, “ice skating in Central Park“ had been one of the items I wished to come true to most – and finally, I was here.
But as I was watching the people on the ice, it struck me: it’s this, this scene I enjoy, because this is exactly what I’ve always seen in movies and played in my head over and over again – I didn’t want to be on the ice, I just wanted to be there when it all happened. So I stayed on the grass, and stood there in happy silence for a while.
After that, we revisited some of our favorite places in the park, but since the weather was rather gloomy and gray that day, we soon headed to 72 Street/Broadway to take the subway to Columbia University.
In hindsight, it must have been nicer on a sunny day, but the campus just didn’t steal our hearts. We wanted to see it for ourselves since it’s an Ivy League School, and maybe we had higher expectations due to our amazing visit at Harvard two years earlier, but we just didn’t resonate with the vibe on campus. Still, the architecture is beautiful and I’d recommend paying a visit. I’ll be sure to give it a second chance when we visit NYC in sunny weather!
To cheer ourselves up in the cold, we headed back to Bryant Park for another cup of hot apple cider, and stayed there until dark. For us it was the perfect place to end our day, but if it’s your first time in New York, I think it would be lovely to take a stroll in the Upper West Side or going all the way back to the Upper East Side and get a sneak peak at how NYC’s rich and famous decorate for the holidays!
Day 5: Breakfast in Central Park & saying goodbye
Sometimes life will give you a second chance sooner than you’d think.
On our last day, we woke up to massive sunshine, so we jumped out of bed and rushed to a Whole Foods Market nearby, and in half an hour we were in Central Park again. This time, the park was glowing in the sunshine, and as I was munching on my fruit salad, all I could think was ‘we almost missed this’. This perfect, still little moment, watching the city wake up, the city I still dream about every now and then.
’til next time, New York!
