This was our first time visiting New York in the winter so we weren’t sure what to expect. We’ve heard how cold it can get and some people even questions why we would visit this time of year with kids in tow. But we actually really enjoyed New York in the winter especially around the Holidays where there are many pop up Christmas markets, the city is beautifully decorated, and there are still so much to see and do! We are sharing our itinerary below to help inspire you with your own visit!

Day 1:

EAT: Took the train into Penn Station, New York and grabbed some NY Pizza Suprema for lunch which was a 3 minute walk from the station. They have a huge selection of pizzas by the slice or you can order a whole pizza of your choice. Warning: their slices are huge but the pizza is thin so if you’re hungry you should order about two slices. After choosing your slices, they warm it up for you in the oven so it comes out perfectly warm and toasted!

STAY: We were able to get an early check in to our hotel Staypineapple, An Artful Hotel, Midtown New York just a few blocks from the train station (we walked with our luggage and kids so very doable). Easy check in that you can do on your phone beforehand so when you arrive they just and you the key! We ended up really loving this location since it was very central to transportation and also within walking distance of many top attractions such as Time Square, Hudson’s Yard, Madison Square Garden, etc. It’s located off of a main street so the rooms were pretty quiet without too much street noise. This location is on the smaller side with only 4 rooms per floor which made for a very peaceful and quiet stay which we loved since were able to get a good nights rest!

Each room is thoughtfully and cleverly equipped with everything you need. We especially liked their smart clock that responds to “Hey Pineapple”. This hotel is also very pet and kid friendly with Connecting Rooms available.

EAT: After checking in we walked around the city toward Time Square and had dinner at Joe’s Home of Soup Dumpling. This location is the newest and elevated version of the famous Original Chinatown location known for their soup dumplings aka Xiao Long Bao (XLB). They also serve a variety of delicious traditional chinese dishes that are popular in Shanghai. Reservations highly suggested.

Day 2:

EAT: Woke up at leisure and walked to Angelina Bakery 8th Street location to grab some pastries for breakfast. This shop is famous for their different flavored croissants and their remastered Bombolones. But really everything we tried here was perfection! There was a line when we arrived but it went quickly and the time in line was actually perfect for surveying all the delicious looking choices to see what we wanted to order. You can also take a look at the pastry chiefs continuously making more goods to restock.

SEE: After filling up we walked to Hudson Yards and the Vessel, taking in the city along the way. If the weather and time allows it, our favorite way to get around is by walking so you can really take in the sights, sounds, and feel of the city. We then took the Subway to Brooklyn and walked over the Brooklyn Bridge. A friend suggested starting from the Brooklyn side so as you walk over the bridge, you can take in the skyline of Manhattan. It was a beautiful but windy day! One of our favorite bridges to walk on.

SEE: After crossing back into Manhattan, we walked to the free Staten Island Ferry building to wait for the next ferry stop. This was a bit chaotic since there’s not actual line, everyone just stands around close to the gate and when the door opens everyone rushes on. Keep your kids and belongings close! This ferry is famous for being free and for getting a glimpse of the Statue of Liberty. Make sure to be on the right side of the boat (going from Manhattan to Staten Island) if you want to see the Statue of Liberty. We were lucky enough to catch the ferry around Golden Hour and the views of the city and Statue of Liberty were lovely. Once you get to Staten Island, you are required to disembark and line up to get back on the ferry to return to Manhattan.

EAT: For dinner, we headed to Chinatown for some cheap and delicious eats. We visited a couple of quick stops so we could try a variety of different food. After dinner we ended the night at Mango Mango known for their Hong Kong Style desserts. They have so many desserts to choose from but are famous for their Classic Dessert options. Their NY Chinatown location is fairly small and they don’t take reservations. They do have online ordering as well as take out option which we saw many people do.

Day 3:

EAT: We went to check out out Cafe Aroma for breakfast and was amazed at all the things they provided. From bagels, sandwiches, donuts, pastries, coffee choices, grab and go options, this place was for sure to have something for everyone. They also serve hot Breakfast Plates such as French Toast and Pancakes and also have a select choice of Acai Bowls. We decided to take our food to go and enjoy it at the hotel to take advantage of our late checkout at StayPineapple (12pm checkout!).

STAY: For our last night in New York we wanted to experience the luxuries and history that New York has to offer. We moved to The Peninsula New York which is located on 5th Avenue among the iconic shopping district. This luxurious hotel has just been newly renovated evoking the essence of a private Manhattan apartment and with the latest in-room technology. Their service is top of the line with every staff being very helpful and knowledgeable. They created such a memorable stay for us with personalized experiences and thoughtful in-room touches that the kids loved! Must note that they also have an indoor pool which was perfect for swimming all year long.

EAT: Our stay came with a private driver which we used to make a visit to Masseria Cafe for lunch. We visited their 9th Ave location for some salads and sandwiches and of course some baked goods for something sweet. They also offer many coffee options to pair with your meal.

SEE: We spent a few hours walking around the American Museum of Natural History and especially loved their Dinosaur Exhibit! You could spend the whole day wandering around these thoughtfully and well put together exhibits. Make sure to buy tickets on line for a fast and easy arrival. The line for tickets at the door was very long and slow!

EAT: We knew we couldn’t visit New York without visiting a Steakhouse! We visited Porter House Bar and Grill which is located in The Shops At Columbus Circle overlooking Columbus Circle and Central Park. They serve all the classic steak cuts as well as Japanese and Australian Wagyu. If you visit on a Tuesday or Thursday they also offer Prime Rib. The service was great and we loved the chic interior of the place.

SEE: After dinner we headed towards Broadway to see Gazillion Bubble Show. This show has been playing in New York City for over 15 years and is run by a family that hold a couple of bubble world records! The show is perfect for families and kids with tons of bubbles and fun to be had for all! The show is just under an hour so it doesn’t run too late.

After New York we took the train to Boston so stay tune for our overview of our visit there!