48 Festive Hours in NYC

If you saw our post from last week, you know that we spent a weekend in New York City doing some seasonal tourist activities! What you may not have seen is the hard-core NYC exploring that had nothing to do with Christmas or 100-foot tall trees.

As someone who lives in Beantown, city life is best described in one word: Manageable. Boston may be the largest city in New England with over 650,000 people, with even more commuting in and out of its limits daily. But even with the large amounts of traffic and bustling sidewalks, it feels small. The different neighborhood are walkable and are collectively only 48 square miles of land. There are dozens of bars and it’s easy to find one that’s exactly what you’re looking for whether it be a local Irish dive bar, a speakeasy, or a hip new establishment with the hottest mixologist. The only confusing part about Boston is its layout; one way streets pop up out of nowhere, the road curves up and around buildings only to dump you out on the road you were just on, and the parking situation is always a mess.

When we think of New York City, manageable is not the word we would use. In fact, the words overwhelming, daunting, and exhausting come to mind. Even still, it has always held a special spot in our hearts. From the amazing films with the city as a backdrop and the business moguls wheeling and dealing on Wall Street to the strength that their residents constantly show, we have nothing but respect for this city (except when it comes to sports – Boston will always be the city of champions).

Since we started dating six years ago, we knew we wants to have a romantic weekend away to NYC around the holidays, to be that couple that holds hands under the Rockefeller tree, stroll down 5th Avenue to window shop, and shoot up the top of the Empire State Building at night to see the reason why this famous is city is dubbed ‘the city of lights.’

This year was our year – we were going! We left early on a Friday morning with an amazing playlist featuring a mix of famous songs about NYC and festive songs to get us in the Christmas spirit. Seeing the skyline as we drove down FDR drive filled our hearts with awe and excitement, which didn’t leave us until we had to say goodbye.

Keep reading for our more details on where to find our favorite pizza, which building to scale besides the Empire State Building, and what to pack (tip: no heels of any kind if you’re planning on walking anywhere).

48 Festive Hours in NYC

Key Pointers

  • If going for the Christmas scenes, take this tip we wish we knew before going. Go to bed early and wake up early. The crowds fill the streets all around 5th Avenue any time between sunset and midnight. Wake up at 5am and go for a walk when there is no one else around. You may not be able to skate, but trust us, your pictures will be magical.
  • Ladies, leave your heels at home. Take it from me, who ended up walking without shoes on for a block – you can do so much more before, after, and during plans if you have the right footwear. Pack a few pairs of flats and sneakers!
  • Unless you’re planning on spending significant time in an amazing hotel, stay in Midtown East. Though it may not be in the middle of the action, it is only three to six blocks from the center of the hubbub. You don’t need a big room either, just a bed and a bath were all we needed for a weekend.

Where to stay: As previously stated, we chose to stay in Midtown East, which is a little removed from the centrally touristy spots near 5th Avenue. We booked our hotel the day of our trip using HotelTonight, and were pleasantly surprised with the options. The Bernic is a small boutique hotel located on 47th between Lexington and 3rd. It was the perfect spot for us; it was a cozy room with a queen-sized bed and a bathroom. They had valet parking for us as well, so it gave us peace of mind knowing we didn’t have to worry about the car or parking situation. The staff was also really welcoming and friendly.


Where to eat, drink, and be merry:

  • Treehaus: If you’re looking to start your day off with a quick bite, hit up this local spot serving up a mean buffet, fresh pressed juices, and fast but delicious breakfast sandwiches. Head to Midtown for this breakfast joint.
  • Ess-a-bagel: New York is known for its unique, soft, thick bagels. Any deli has them. But if you’re looking for a great place in Midtown East, hit up Ess-a-bagel for any sandwich you want; we had a pastrami, egg, and provolone on an everything and a bacon and cheese on an onion. Word of caution, be prepared to wait if you go anytime after 8am.
  • Blackwell’s Restaurant and Pub: We never really ate lunch while in the city. But we hit up Blackwell’s for a mid-afternoon beer and snack. Order the mac and cheese and any of their salads. Surprisingly fresh and fast service, located right across the street from our hotel in Midtown East.
  • Juliana’s Pizza: Dubbed as one of the top places in Brooklyn to grab a slice, Juliana’s claim to fame is their coal burning oven. This cozy establishment plays Frank Sinatra, sells canolies and has one of the best pizza’s we’ve ever tasted. We ordered the pepperoni which was more like a fresh mozzerella, basil and pepperoni flatbread from heaven. You have to hit this place up if Brooklyn is on your list.
  • Black Barn: We went here for our anniversary dinner as it was pricier and a little more intimate. This establishment has amazing selection of wines and cocktails complimented by a modern take on farm-to-table comfort food. We had the special of butternut squash gnocchi with short rib and the menu staple, pumpkin ravioli with prosciutto. You can’t go wrong with anything here. The wait staff is also quite friendly and knowledgeable of its Madison Square Park location!
  • Esanation: After walking away from the Rockefeller Tree chaos Saturday evening, we ended up in Hell’s Kitchen. We didn’t make a reservation anywhere and passed Esanation’s neon door, immediately drawing us in. Amazingly, this Thai joint was delicious, hip, and fun. Definitely seek this place out, even if it’s only for a drink.
  • Rolf’s Restaurant: You know those pictures of the elaborate ceiling decked out in Christmas paraphernalia? We mean everything from ornaments and lights to icicles and porcelain cherubs. Well this is your place. Plan on only a drink or making reservation months in advance of your trip. A few minutes is really all you need to capture the point of this place. It’s a must.

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What to do:

  • Head to Brooklyn for a few hours: When we first got to NYC, we had a few hours to kill before our hotel check-in. We decided to drive across the Brooklyn Bridge to Dumbo, grab some pizza, and the double back and walk a portion of the bridge (which really is a different experience than driving over). Head here for an adventure of your own!
  • Head to the Top of the Rock: If you’re looking for a view with less crowds, head to the top of the Rockefeller Center instead of the Empire State Building. You have a semi-unobstructed view of central park and can clearly gaze at the Empire State Building, Chrysler Building and One World Trade Center.
  • Walk around the Christmas Tree and Rockefeller Center: It’s a marvel both by night and day. There are less crowds in the hours of daylight, and you have more of an opportunity to ice skate, if that’s a must on your list.
  • Window Shop on 5th Avenue: The window displays on this lux portion of 5th Ave in Midtown are out of this world, especially this time of year. The amazing pieces of fashion and the creativity are unlike anything we’d ever seen. Be sure to do it both during the day for a Breakfast at Tiffany’s vibe and again at night to see the shadows and lights come to life.
  • Central Park’s Wollman Rink: If ice skating in the city is a must on your list, you have to venture to Central Park’s Wollman Rink. This famous rink is in the heart of the park surrounded by trees and skyscrapers – it doesn’t get much more New York than this!
  • Eat Late Night: You’re in New York City, the city that never sleeps. You have to have a late night snack. We chose ‘$0.99 Pizza’ because, hey why not get two slices for two dollars at 12:30am?

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