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Long Island parents' dilemma: When to let kids go into NYC on their own

Teens wait on the platform at the Hicksville

Teens wait on the platform at the Hicksville LIRR station for the train to Penn Station. Some Long Island parents say they let their kids head to Madison Square Garden alone for sporting events and concerts.  Credit: Morgan Campbell

When 14-year-old Sienna Sanchez of Long Beach was invited to join a group of friends heading into Manhattan to celebrate a 15th birthday, she knew it was a long shot that she’d be allowed to join them. “My parents don’t let me go into Manhattan yet. They think it’s dangerous,” she says.

Still, the high school freshman asked, and Sienna got her mom's message with just a look. “She said, ‘I know, I can’t go,’ ” mom Sandy Sanchez says.

Sienna’s request poses a dilemma that many parents in suburban Long Island grapple with: When is it time to allow your children to venture into the city alone with friends? “At one point, I will let her,” Sandy says. But not just yet.

From taking the Long Island Rail Road alone to exploring unfamiliar neighborhoods and navigating the subway safely, the city poses plenty of new experiences that can be exciting for teens but concerning for parents. Here are nine questions parents say they consider when deciding whether to green-light a kids-only adventure in the Big Apple.

1. How will parents know they arrived safely? “We text them when we’re on the train, when we get to the city and when we plan on leaving,” says Ashley Cassano, 14, a ninth-grader from Plainview who likes to go clothes shopping with friends in SoHo. Some parents say their kids must agree to be vigilant about keeping their phones charged up so parents can use apps like Life 360 to track their location. Kids also must keep in touch regularly.

2. Will they need to leave Penn Station? Anthony Macchia, 15, a Lynbrook sophomore, says he’s been permitted to go to sporting events at Madison Square Garden, but only because he doesn’t have to leave the Penn Station complex to do it. “He’s only been allowed to go to a Knicks game so far,” says dad Ralph Macchia, an attorney. “He never really ventures out of doors into the city.” Anthony says he doesn’t mind the restriction. “If I’m going to the game, I’m going to stay at the game,” he says. Other teens say they’ve been allowed to go to MSG for concerts such as Post Malone or Brockhampton with friends.

3. Are they familiar with the layout of the city? Sandy Sanchez says that before she’ll allow her daughter Sienna a friends-only trip, she plans to take her into Manhattan herself for a tutorial to “arm her with knowledge” by exploring the streets. “She doesn’t know the city,” Sandy says. “I feel it’s very complicated." Eileen Clarke, a ballroom dance teacher from Lido Beach, says she feels more comfortable letting daughters Stella Ambroise, 16, a junior, and Summer Ambroise, 14, a freshman, go to the city with friends if those friends are city-savvy. “I grew up in Queens, so the city for me was 15 minutes away,” Clarke says. “I feel like they’re a bit more sheltered growing up on Long Island. I think it’s important when you go to New York to look like you know where you’re going, and not look like you are completely country bumpkins.” 

4. Will they be with a group? "As long as she's with a group, I usually feel comfortable with her venturing out," says Dionne Jean-Louis, an occupational therapist from Baldwin whose daughter, Jasmin, has been allowed to go into Manhattan since she was 16. "In the event of an emergency or if something goes wrong, people in numbers always work better than those by themselves."

5. Will they depart the city before dark? Jasmin, now 17, says she always has to let her mom know where she’s going, who she’s with and what train she’s catching home. But she hasn't been allowed to be in the city after dark. “At night is a different story,” Jasmin says. “It’s just a different environment.” Mom Dionne says now that her daughter is approaching 18, she would probably let her go in the evening if she was going to see a show, for instance. 

6. Will they be taking the subway? While her daughter is allowed to take the LIRR to Manhattan with friends, venturing into a subway train is a no-no, says Simone Levy of Plainview, a benefits consultant and mom of Allison, 14, a high school freshman. “We’re not sure they can navigate it, the different trains,” she says. She jokingly adds, “I can’t navigate it.” When Allison visited the city recently, she and her friends got around using Uber. 

7. Can they be trusted to follow your rules? “I think compared to a lot of other people, we’re really responsible and our parents trust us,” Allison says. Says parent Jean-Louis: "For me, it comes down to the maturity of the child and how much you trust they're going to follow your rules if you aren't with them."

8. Is it a special occasion? Allison Levy was allowed to go to Manhattan with Ashley Cassano and other friends on Dec. 31 because they were off from school, with instructions that they “absolutely not” go to Times Square, which was being set up for the New Year’s Eve ball drop. After their first trips to the city, “they were so proud of themselves. They said, ‘This is a game-changer.’ Now they feel they’re going to be able to go all the time,” mom Simone says. She quickly put the kibosh on that idea.

9. Are mom and dad ready for this? “I was very nervous the first time,” says Levy. Clarke offers this perspective: “I feel like it’s my job as a parent to make them self-sufficient. Being street-wise takes time and the experience of being on your own with peers. That’s the only way they’re really going to learn.” Joe Cassano, director of finance for a tech company, says the fact that Ashley is his third child makes loosening the reins easier. “If it was my first child, it’s a little different. You’re a little more apprehensive,” Cassano says. “When they’ve all done it, and everyone’s survived, you’re a little more easygoing.”

Technology can be a parent's best friend when kids venture into Manhattan. Here are some features that can help keep kids safe and parents reassured:

  • The MTA's official LIRR TrainTime mobile app can help kids find their trains easier. Select which hub you're leaving from and where you're headed and it'll provide an in-hand train schedule. The "arrival countdown" lists which track each train is arriving on, so there's no need to linger in Penn Station. The onTime LIRR app lets parents see where each train is along the route and when it pulls into Penn Station.
  • Location apps such as Life 360 or Find My Friends let parents track their children's movements through the city.
  • Free kiosks called LinkNYC, found on several streets in Manhattan, provide free Wi-Fi and map access, a 911 help button and an ability to charge phones to make calls. To find LinkNYC hubs along your child's route, visit
  • The iPhone map app offers the option of switching to transit directions, which can help teens needing to use public transportation. It maps out subway lines, bus routes and LIRR directions.
  • Forewarned is forearmed: Check online NYC calendars before the trip into the city to make sure recurring events such as SantaCon, Fleet Week or a parade that shuts down streets around Penn Station won't cause unwanted travel complications.


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