6-Day New York City Itinerary with a Tween and a Teen

When the time came this year to start planning a Spring Break trip, it was my tween daughter who suggested New York City. My boyfriend and I had taken the kids to Florida and Washington, DC for previous Spring Breaks, but we were holding off on NYC until we thought the kids were old enough to appreciate it and to be able to physically handle all the walking a trip like that would require.

As I started researching New York, I realized it was the perfect time to take my 11-year-old daughter and my 15-year-old son. So what did we do during our Spring Break in New York City? Check out our 6-day itinerary.

Keep in Mind

Some attractions, like the One World Observatory and the Empire State Building, offer ticket options with no advanced planning. You walk up to the ticket booth and buy your ticket. Other attractions, like the Statue of Liberty, should be booked well in advance. Both crown and pedestal tickets were unavailable when we first decided to go to New York two months prior to our trip. Ferry tickets to Liberty Island seemed wide open so we waited until we arrived in New York to book because we wanted to pick the best day as far as the weather. We were shocked to see there was only one time slot available with Statue Cruises for our entire stay. We booked it immediately, even though the weather report called for rain, thankful we wouldn’t miss one of New York’s best attractions because of our poor planning.

As far as money-savers, the CityPass is an option, but it’s not always the best deal. Before leaving, we figured out which attractions included in the CityPass we would actually go to and compared it to the total cost of going to those places without the pass. For our itinerary, the CityPass wasn’t the way to go. When doing your own calculations, keep in mind any discounts you might get (e.g., military discounts) and reduced rates or free admission for your children.

And remember that traveling with tweens and teens is different than traveling as adults. In some ways, traveling with these mini adults is easier than being on the go with babies and lugging strollers and car seats around. But in other ways, it’s more complicated because they’re old enough to have input on what they’d like to do. And what they want to do doesn’t always mesh with what you want to do, so discussion and compromise are always in order.

I have several tips for traveling with tweens and teens, but the best advice my family followed while in New York was to schedule laziness. Every day we had adventures in the morning and then headed back to our hotel for two to three hours of downtime, quiet time watching tv or reading or showering. This time was not wasted. Those hours allowed our legs to recover from all the walking, our bellies to digest the yummy food and our brains to rest from all the stimulation. Then we moved on to evening adventures!

Day 1

The first day was mostly a travel day. We originally thought we were going to take the train from Virginia to New York, but after pricing train tickets versus driving and paying our hotel’s daily parking fee, we chose to take the less expensive route and drive.

Driving allowed us to leave when we wanted to and to pack extras like a large snack bag, a cooler and extra pillows. And seven hours after leaving our house, we pulled up in front of the New Yorker hotel and handed our car over to the valet, not to be seen again until departure day.

After checking into the hotel, we set out to explore. We wandered around Times Square before finding our way to the Museum of Modern Art, or MoMA, a destination chosen for our first evening because every Friday from 4:00 to 8:00 PM admission is free. We arrived just after 6:00, and while it was crowded, we didn’t have to wait in any lines to get our free tickets.

I don’t know about all tweens and teens, but mine had to be coaxed to MoMA with the promise that this would be their only museum of the trip. And while they weren’t as excited as I was to see the Jackson Pollock exhibition or Salvador Dalí’s The Persistence of Memory or Vincent van Gogh’s The Starry Night, I did catch them smiling and snapping pictures on their phones.

After the MoMA, we decided to get acquainted with the New York subway system. Our goal was to either walk or take the subway everywhere, avoiding the more expensive taxis and Uber or Lyft. Our first step was to purchase a seven-day unlimited ride MetroCard for each of us. Even though we would only use them for five days, the $32 cards allowed us the flexibility to take the subway as much as we wanted, as well as allowing us to make mistakes by taking the wrong line (which we did).

Pizza can be found just about anywhere in the city, so we grabbed a couple of slices before heading back to the hotel for the night.

Day 2

After studying the subway map in our guidebook, my boyfriend led us to our first stop of our second day in New York: Lower Manhattan.

We got off the subway and walked to the Oculus, a subway station and shopping area inside a very cool building.

Next we walked over to the 9/11 Memorial. It’s impossible to describe the emotional experience of looking at all the names of those who died inscribed on the memorial pools and seeing the Survivor Tree, the Callery pear tree that endured the 9/11 attacks and was rehabilitated back to health. Even my kids, who were born years after the events of 9/11, felt the heaviness as my boyfriend and I talked about where we were when it happened.

There is also a 9/11 Museum, but we didn’t go in. Keep in mind the memorial is free, but the museum is not.

As we waited for the fog to lift, we walked through Brookfield Place, a mall a few blocks away from the 9/11 Memorial. We ate an early lunch at Hudson Eats in Brookfield Place, an upscale food court with options for everyone, including bagels, pizza, sushi, tacos, burgers and cupcakes. And we saw cherry blossoms! (I love cherry blossoms.)

By the time we finished eating, the fog had disappeared, and we bought tickets to the One World Observatory. The elevators climb 102 stories in 47 seconds, leaving visitors with stunning 360 degree views of the city below. You’ll be offered a virtual reality guide that labels the skyline for a fee, but we skipped that.

After a subway ride and some hotel downtime, we headed back out for some shopping, sightseeing and dinner. We let the kids guide our shopping choices, which included Midtown Comics, the M&Ms store, the LEGO store and FAO Schwarz. These spots helped us stumble upon Rockefeller Center, where we watched ice skaters and snapped photos of famous places like the Today Show building. Because we had already done the One World Observatory, we skipped the Top of the Rock Observation Deck.

Our next planned stop was dinner at Ellen’s Stardust Diner, home of the singing servers. Unfortunately, my kids didn’t want to see a Broadway show, so Ellen’s Stardust Diner was our version of a Broadway experience. They don’t take reservations, and we waited a half hour in line, but it was well worth the wait. As we enjoyed sandwiches and shakes, the waiters and waitresses sang show tunes mere feet away from us, belting out songs like Frozen’s Let It Go, Annie’s Tomorrow and a fun Mamma Mia montage. This was, by far, my favorite dining experience of the trip. I didn’t want to leave.

Day 3

Today was our Statue of Liberty day, and we woke up thrilled to find the weather report had changed and the rain forecast turned into sunshine. That time slot we were lucky to grab was for 10:00 AM, but because we still weren’t confident of our subway navigational skills, we left early and arrived at the Battery Park ferry at 8:30. We killed time by walking a few blocks to check out the New York Stock Exchange building and the Charging Bull in the Financial District.

Back at Statue Cruises we went to will call to get the tickets we bought online, and we ended up getting free pedestal upgrades just because I asked. We were told the first 100 visitors of the day are eligible for the upgrade, but only if requested. So instead of taking the ferry over to Liberty Island and simply walking around the base of the Statue of Liberty, we were able to go inside and climb the stairs up the pedestal.

Ferries leave every 20 minutes, and we got on an earlier ferry instead of waiting until 10:00. Liberty Island was completely covered in fog when our ferry pulled in. We climbed the 354 steps up the pedestal and asked if we could keep going into the crown, but we were denied.

By the time we walked back down the stairs and came out at the bottom of the pedestal, the fog had lifted.

After admiring the Statue of Liberty up close, we took the ferry to Ellis Island, an immigrant inspection station from 1892 until 1954. I was able to do a passenger list search and found my mother, my aunt and my grandparents who came from Holland in 1952 for a vacation, a lovely stumble upon my family history.

We took the ferry back to Battery Park and hopped on the subway back to Penn Station, lunching at the Shake Shack on our stroll back to the hotel for our daily midday rest.

Our evening adventure brought us to Hudson Yards in Chelsea on our way to walk the High Line, an elevated public trail built on a freight rail line on Manhattan’s West Side.

We ate dinner at a diner we found on our walk back to our hotel. (There’s definitely no shortage of places to eat in New York City.)

Day 4

I checked the weather report before we left the hotel. No rain. When we got off the subway in Brooklyn? Rain. By the time we got to the Brooklyn Bridge? Torrential downpour. We were soaked to the bone, but we still crossed the Brooklyn Bridge. And because of the bad weather, we shared the bridge with only a handful of other visitors.

Because of our wet clothes, we had to go back to the hotel to change and use a hair dryer on our shoes, eating lunch from the hotel diner in our room.

The rain had stopped by the end of our midday rest, so we got back on the subway to hit Greenwich Village, SoHo, Little Italy and Chinatown. The kids loved Dylan’s Candy Bar, and we got some authentic Chinese food for dinner in Chinatown. We got back to the hotel for the night minutes before the rain started again.

Day 5

This was our final full day in New York City. We hopped on the subway again and found our way to Central Park, where we rented bikes and rode six miles around the park.

We saved this adventure for the last day because it was a beautiful weather forecast filled with sunshine. This was my tween’s favorite day of the whole trip. (Getting soaked on the Brooklyn Bridge was my teen’s favorite. He thought the rain was hilarious.)

We rented the bikes right outside Central Park for two hours at $20 per person. If I had to do it again, I would have paid the $25 rate for three hours because we had to rush back to return them on time. We stopped at different playgrounds for the kids to run around, rested while eating hot dogs and veered off the main road to see various landmarks like the Bethesda Fountain.

In search of food, we found ourselves in The Plaza Food Hall and tried some dumplings. Still hungry, we got pizza closer to our hotel and then relaxed for a few hours.

For our last dinner in New York, we went to Juniors Cheesecake in Times Square. The burgers weren’t bad, but the cheesecake was delicious.

Our last adventure was the perfect New York City finale: the Empire State Building at sunset.

We loved the day views from the One World Observatory, but the night views from the Empire State Building’s open-air 86th Floor Observation Deck were even more spectacular, partly because of the endless lights and partly because we could go outside.

Day 6

All good things must come to an end, and we hit the road in the morning to head back home and back to the reality of my tween’s softball practice and my teen’s track meet. We left totally exhausted, but with tons of fun memories and a newfound love for New York City.