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Best Weekend Family Trips: Travelling With Teens to New York City (NYC)

Updated on July 18, 2011
Ice cream in Central Park was a perfect break after the Natural History Museum.
Ice cream in Central Park was a perfect break after the Natural History Museum.
If football doesn't work out there is always Wall Street.
If football doesn't work out there is always Wall Street.


  1. Keep It Short. They won’t want to be away from their friends for more than a few days.
  2. Plan Your Meals. Teenagers (especially boys), can make a huge dent in your travel food budget. If they are big eaters, visiting a buffet or having a big meal midafternoon could keep the costs down, and grabbing dessert later in the evening will tide them over until breakfast.
  3. Stay Out Late. You may be yawning by 10:00 pm, but they are just getting wound up. Plan an evening event. Tickets for later theatre shows on weeknights are often discounted, or heck, go to the late late movies at 11:00 pm. You are on vacation and no one has school the next day!
  4. Hang Out And Window Shop . This can be combined with item three, as many tourist areas of big cities such as New York City, Chicago, and Boston get busy in the evening. Walking around, grabbing a pop at an outdoor café, and window shopping are all popular teenage activities anywhere.
  5. Pick one activity or event that your kids would not normally do. After all, travel is all about new experiences. If you have followed the previous four tips, they should be relatively cooperative with this last one.

Happy Travelling!

Times Square at Night
Times Square at Night

How I Found New York City Flights and Hotel Online for Great Discounts

“Pack your bags, boys - we are going to New York City!” This was the text I sent my teenage sons one day last April. I had always wanted to take a family trip there, but the expense and logistics of a single woman travelling with small children in a busy unfamiliar city had always seemed prohibitive. And then one Monday the children weren’t so small, the expenses were manageable, and I conquered the logistics. By using great internet travel tips and booking directly with the airlines and hotel we saved a bundle. Here is how we did it.

WHO: One almost middle-aged mother and two teenage sons.

HOW: It all began with an email notification from Travelzoo, a great source of travel deals including flights, hotels, and activities. The email was for a 24 hour seat sale on Jetblue. I already had a $100 credit with this airline from previous travel, and by booking directly through their site I was able to use it in conjunction with the seat sale. With taxes and my credit the three of us were able to fly round trip for just under $300.00. The cost of parking at the Fasttrack lot across from Niagara International Airport in Buffalo was reduced to $7.49/day with the coupon I had from the latest issue of CAA magazine. As we had packed lightly (one overnight bag each), we didn’t have to check any luggage and were able to take the AirTran and subway easily from JFK Airport to Manhattan. It was a short walk from the subway to the Roosevelt Hotel, which I also found as a 24 hotel sale on Travelzoo, and booked through the Roosevelt’s website. I was a little concerned with the mixed reviews on Tripadvisor, but the deal was too good to pass up as we were able to get what was normally a $360 room for $169 a night. I was delighted to learn that children up to and including the age of 18 stayed for free. Our room had two queen size beds, and I slept in one while the boys shared the other. The room was small (which is normal for Manhattan)but clean in a great location at the corner of Madison and 45th, right beside Grand Central Station. There are several reasonably priced diners within a short walk of the hotel, so we didn’t bother with the restaurant there.

WHAT: A spur-of-the-moment four day, three night family trip to New York City. As we live 45 minutes from Lester B. Pearson Airport in Toronto and just over an hour from Niagara International Airport in Buffalo, New York, we had our choice as to which airport to use. Much less expensive to fly from Buffalo. I had our flights, hotel, and theatre tickets booked by Tuesday morning, and we flew out on Thursday. Our visit included a Broadway show, touring the Natural History Museum, eating ice cream in Central Park, and shopping at South Seaport and on 5th Avenue (at the huge Abercrombie & Fitch, of course). We also visited Grand Central Station, Times Square, Central Park, Ground Zero, and Wall Street.

WHY: The boys had always wanted to go to NYC, and my younger son had been there the previous year on his grade eight school trip (whatever happened to going to Ottawa or Quebec City?) He had a fantastic time and wanted to go back. The weather was good and the discounts for travellers were fantastic as tourism had plummeted due to the recession. At fifteen and seventeen my sons were the perfect ages for this trip. I didn’t have to pack colouring books or bulky activities; their ipods and Blackberries kept them entertained. I didn‘t have to carry their luggage or their sweaty little selves, and no one threw up on me in the plane. This alone made it a vast improvement on our last trip. A bonus was that they were so thrilled to be doing something spontaneous and adventurous (they were shocked that I didn’t spend at least a year researching, planning, and budgeting the whole thing) that they took turns carrying MY luggage!

WHEN: Late April 2009. The weather was great - mild and sunny. This was important as many of our activities would involve walking and being outside. We flew out Thursday morning and returned Sunday afternoon. Using Jetblue’s website I found cheap flights these days, and the Professional Development Day scheduled for Friday meant the boys would miss only one day of school. Arriving in NYC on Thursday allowed us to attend a discounted Broadway show on the Thursday evening so we saw Chicago at the Ambassador Theatre. I found the tickets on Travelzoo and purchased them through Audience Rewards.

Our Thursday night theatre tickets were  the fourth row and 65% off.
Our Thursday night theatre tickets were the fourth row and 65% off.

WHERE:The Big Apple - New York City. This is a GREAT destination for families with teenagers. So many of the television shows and movies that they have seen feature the city. When we were in Grand Central Station my seventeen year old was excited to recognize the spot where Serena stands in the opening credits of Gossip Girl. The area around Central Park had the boys reminiscing about their favourite Law and Order episodes. The Dakota Building and Strawberry Fields were must-sees for my fifteen year old Beatles fan.


While we all enjoyed the show, the museum, and the shopping when I asked my sons this morning what they liked best about that trip they both agreed that it was the energy and people of the city. Sitting in the middle of Times Square at midnight on Friday night, at an outdoor café in South Seaport on Saturday afternoon, even at Central Park were what they liked the most. They also mentioned two things that I had almost forgotten. When booking our tickets I hadn’t noticed that the NFL draft was also scheduled that weekend, and we happened to be passing Radio City Music Hall on Saturday morning as the potential players and personnel entered the building. Very cool for two high school football players. A more serious event was what appeared to be a police funeral on Sunday morning being held at St. Patrick’s Cathedral. The road was closed to traffic, and the effect of all the soberly dressed and uniformed men and women walking silently up the middle of Fifth Avenue was very dramatic.

A year and a half later, we all agree that it was a fantastic long weekend. If you are planning a trip with teenagers, the following points will help to smooth the way.


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