5 Days in New York with a 5-Year-Old

New York City—one of those trips that makes you really excited…but also a little nervous, if you’re traveling with kids. In June, my husband and I took our 5-year-old son Harry to Manhattan, and as much as I love that city, there’s something intimidating about it.


Additionally, I knew this trip was going to be very different from our past New York trips, which have been filled with trendy restaurants, theatre, shopping on 5th Avenue, and boutique hotels. Traveling with a kid required more planning and research to discover how we could make the trip fun for everyone without stretching our 5-year-old beyond what he’s capable of.

Essentially, we didn’t want to overload his senses, which is very easy to do at any age in New York City. So, I planned five days there (instead of what would’ve been a weekend for my husband and me solo) because I wanted to have a loose itinerary. To do the trip justice and enjoy our time, we needed the extra days.

Read Part 1 below to see how my family spent our days in New York City, and then check out Part 2, for even more of my Big Apple travel tips.

  • See the city at the One World Observatory . We flew into New York on an afternoon flight. I’d made reservations for us to head to the new One World Observatory at One World Trade Center an hour before sunset, which is the perfect time of day. You’re able to see the city from all different vantage points—light, dusk, and dark. Seeing the city from so high up got Harry really excited for all that we had planned over the next five days.


  • Plan to walk through Time Square—a lot. The first morning we were there, we took Harry to see Times Square. The glittering lights and hugeness of it all had him hooked. He was absolutely mesmerized. Times Square is sensory overload to max, but kids love it. We went back in the evening, too, to see the difference between day and night.


  • Take a free ride on the Staten Island ferry. There are lots of ways to see the Statue of Liberty, but one that many tourists don’t consider is the free ferry. It’s super easy and convenient to public transportation (the subway goes right there). Harry loved every minute of it. We planned our trip during a non-commuting time (3 p.m.). The ferry wasn’t busy, and they allow drinks and snacks. We went right past Statue of Liberty, took pictures, and the whole experience took about 30 minutes. It was perfect because that happens to be right around Harry’s limit. He’s not at an age where he’d have the patience for waiting in lines and then touring Ellis Island. This approach enabled us to see the landmark up close and then go on about our day.


  • Spend a day in Central Park. We love parks and playgrounds, and spend a ton of time in them in Chicago. When we went to Central Park, the weather was nice, and the Victorian Gardens were open.

NY_ParkIn the summer, the Victorian Gardens feature all different rides for little kids. Get a bracelet that allows your kids to ride unlimited rides, and then snap pics of them having fun. Afterward walk the park and take in its beauty.  Run and play together, there are giant boulders and hills throughout the park that Harry loved climbing. It was such a nice contrast from the dense city of Manhattan—to go to this beautiful, open space. The trip to Central Park ended up being one of our favorite takeaways.


  • Take in a Broadway show. This was Harry’s first Broadway experience, so for him to really be drawn in, we needed to splurge on good seats. We chose a Lion King matinee, opting for a story he was familiar with at a time of day when he wouldn’t be too worn out. The decision was totally worth it. Harry felt like he was in the middle of the show as the animals rushed past us down the aisle, and my husband and I were really impressed with how into it he was. The experience showed me that 5-year-olds can sit through shows, and if we’d been staying longer, we’d have gotten tickets to Aladdin, Matilda, or another kid-friendly show.


  • Walk down The Highline. This is a park that runs through several New York blocks on the old elevated train tracks. It was reinvigorating to see dense New York City from a different angle—looking over the river on one side and toward the city on the other. We were there on a hot summer day.

WaterGardenSprinklers were going, and there were lots of people happy to be out. Make sure to stop at People’s Pops, the gourmet popsicle stand. It’s delicious, and made a nice addition to our time on The Highline.


  • Ride the subway, and check out different neighborhoods. We took the subway to Little Italy, Chinatown, the Upper East Side, Tribeca, Chelsea, and more. Harry loved adventuring and working with his dad to load up our transportation card. The subway in New York has so many tunnels, stairs, and different levels. Harry truly enjoyed being in these dark tunnels, and coming up in a whole different part of the city from where we left. It was a big treat for him. Every time we would decide what to do, he would say, “Should we jump on the subway?”


For more of our New York adventures, tips, and tricks for conquering the city with a 5-year-old, read Part 2!


Sarah is a Chicago based travel writer and the founder of WellTraveledKids.com. Sarah's best travel companion is her sweet 5-year-old son, Harry. Her favorite trips include a great luxury hotel stay, quality family play time, lots of champagne, and decadent chocolate covered strawberries.

'5 Days in New York with a 5-Year-Old' have 3 comments

  1. April 14, 2016 @ 8:12 am Win a Free Vacation with National Geographic, and Celebrate 100 Years of National Parks | Well Traveled Kids

    […] year, we began exploring the National Parks with my then 4-year-old son, Harry. He loved The Statue of Liberty, as well as Pu’uhonua o Hōnaunau National Park and Volcanoes National Park on the Big Island of […]


  2. admin@mammalovestravel.com'

    July 8, 2016 @ 9:12 am Natalie

    NYC is on our family’s bucket list. Although my daughters are a little older (aged 12,8 and 6) they would love every single one of these activities! It’s a great list, totally doable with little ones.


    • August 13, 2016 @ 10:10 am Sarah Hirsch

      NYC ended up being one of our favorite family Adventures, I bet your girls will love it!!


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