New York City 3 1/2 days ~ Itinerary with a 5-Year Old

So recently I received a notice from my skymiles account - hey lady! You have a free companion ticket offer that expires if you don't use it by the end of January! Not booked by end of January - used... so... I said HEY! Anyone want to go anywhere? (Mind you this was mid-December). My sister looked at me like I was crazy. She's not wrong. I said well I can just go by myself somewhere with Lindsey! Then I said - hey friend of mine who is also a little crazy, wanna go to New York, in the middle of January, with a 5-year old? And being apparently as crazy as me she said sure, let's do it!

So this is my recap of our packed long weekend in the freezing cold of New York in January, with a 5 year old. Let me repeat. With.A.5.Year.Old. I hope she remembers something of this trip - it was pretty fantastic to take her. It's a completely different trip when you take young kids, I just think there's something really special about exposing them to new places, the ups and downs of traveling in general, etc. I hope it will make her an even stronger, braver, more open-minded young woman. Plus, let me be totally honest. I adore my kiddo and I have a blast taking her everywhere - even when we're both cold, hungry, and crying. Yes, both.


Day 1 (Friday)
  1. Arrived at our hotel around 1:30pm (stayed at the Washington Jefferson hotel - easily walkable to just about everything from here)
  2. Late Lunch at Ellen's Stardust Diner (expensive for the food you get - but the entertainment factor was completely worth it!)
  3. Disney Store (wow - Lindsey stimulation overload!)
  4. M&Ms World (all the colors of the chocolate!)
  5. Times Square
  6. Walked to MoMA - we got lucky and it was free admission that evening. I saw Van Gogh's Starry Night. I had a moment. Lindsey had meltdown #1 of the trip. 
  7. Dinner at Famous Amadeus Pizza 
  8. Stopped at Maison Kayser for coffee and tried one of the desserts; Lindsey wasn't impressed with the cocoa
  9. Ice Cream at Holey Cream (check them out; Donuts & Ice Cream...!)

Day 2 (Saturday)

  1. Breakfast at Pick A Bagel (NY bagel #1)
  2. Rockefeller Center - visited FAO Schwarz and a quick stop in at the Lego Store
  3. Met up with friend's nieces L & L (who Lindsey fell instantly in love with). Took the Subway to the Ferry Terminal, got hustled into tickets for a Statue of Liberty Cruise instead of taking the free Staten Island Ferry, took a ridiculously long bus ride to departure point, rode the Queen of Hearts out past Ellis Island and around the statue. Waited until we froze to death for a bus ride back. Bus driver wouldn't depart until 5 people got off the bus, saying we were over capacity. FINALLY got going, got off at the 9/11 Memorial - had another altercation with the bus driver who let everyone except L & L off, and made them pay to get off the bus).
  4. 9/11 Memorial (Lindsey had meltdown #2)
  5. Went back to Hell's Kitchen for Dinner (insert quintessential scary subway experience with a person who did a WHOLE lotta cussing and accusing everyone who was paying any attention to Lindsey a f*ing predator; on repeat for several stops) - options become limited in the evening when you have a kiddo in tow. Went to a Georgio's Country Grill for dinner (really wanted to go to Valhalla's - after 5pm no one under 21 though)!
  6. Ice Cream at Holey Cream


Day 3 (Sunday)

  1. Had breakfast at the Cosmic Diner and said goodbye to L & L
  2. Walked to Herald Square and saw the 1st Macy's
  3. Empire State Building (cold and beautiful - Lindsey met King Kong and loved him)
  4. Best Korean BBQ at Kobeque in Food Gallery 32 in Koreatown for lunch
  5. Went back to the hotel and everyone napped for a bit (Lindsey woke up from her nap crying that it was already dark outside)
  6. Walked back out along Broadway, stopped in at a couple shops. Lindsey had a BLAST in the BTS Store - she posed with all of the statues at least twice. 
  7. Midtown Comics (sadly, couldn't bring everything back with me)
  8. Carlo's Bakery (the baked goods we picked were disappointing, but the free hot cider samples were delicious!)
  9. It was very cold and Lindsey was completely over the weather at that point
  10. For dinner that evening we ordered in - Thai. Neither of us loved what we picked that much


Day 4 (Monday)

  1. Breakfast at Bread Factory (NY bagel #2. Lindsey had pizza for breakfast) 
  2. Got our mandatory "I love NY" goodies before we returned to the hotel to pack up
  3. Packed and left luggage at the front desk of the hotel (the hotel staff were amazing I might add)
  4. Headed back out into the cold - found a CVS and bought a fluffy blanket for Lindsey. It was about 8 degrees this morning and she was miserable! Wrapped her up like a burrito and she was much happier
  5. Central Park (bike ride around the park / took pics / froze to death)
  6. Visited the Shops at Columbus Circle for awhile - had coffee and an eclair and people watched / thawed before we braved the walk back to the hotel
  7. Grabbed pizza to-go from the Bread Factory for lunch which we took back to the hotel and ate in the lobby before heading out for the airport at about 3pm or so for our 7pm flight 




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