New York City with Teens (and Tweens)
A little insane, but what the heck—this year’s family vacation would be a trip to New York City with teens (and a tween) in the dead of summer.
The Plan
Rent out our house to fund this year’s family wander ✔️
Fly the whole family to NYC ✔️
Begin our search for the perfect pizza ✔️
Day 1—Sanctuary Guest Suites & Katz’s Deli
On my last visit to the city (for a New York City Food Tour in April 2010), I bonded with Greenwich Village. This trip would be the one where this family would leave the security of the Midtown tourist zone and experience a different side of New York.
Leave it to me to find someplace crazy to stay. (This trait of mine sometimes delights and often disgruntles my family.) Even I was slightly concerned when we landed next door to a Hell’s Angel clubhouse. Was it possible that the “Inter-Faith Community” operating Sanctuary Guest Suites was an atheist motorcycle gang?
I held my breath as we were escorted up four flights of practically vertical stairs (dragging all our luggage). When we entered the room, I began to sweat…not because of summer temps, but because it was about the size of two large walk-in closets and was missing one of the two queen beds promised in my reservation. Before I could calculate my next move, the manager scurried away and the family turned on me…
“Hun, where is the third bed?,” asked Dad.
“Mooommmmm, this neighborhood is SCARY…and this place is TINY!,” whined the tween.
“Great job, Mom…you’ve done it again,” chimed in the teen.
Before a full-fledged riot began, I whipped out my Smartphone and dug up the reservation confirmation—the one I hoped confirmed that this was definitely NOT my doing. Relief flooded through me—at least momentarily—when I found it. I had booked a room with two queen beds—and a fold-out couch—and I sent Papa Bear out to collect on it. Success…but, not until the next day. The staff wisely offered to transfer our bags back down to the first floor into our adequately bedded room. THAT was a near miss.
Rest for we weary would have to wait until we got some much needed sustenance. At the recommendation of our taxi driver—and confirmed by Yelp— we walked the couple of blocks to Katz’s Deli.
Opened in 1888, this is the same place where Meg Ryan demonstrated true pleasure to Billy Crystal. I almost did the same thing—while we ate. Everyone must dine here at least once in their lifetime. Even if I withheld food for days, I still wouldn’t be able to finish an entire sandwich by myself. A 4″ high stack of mind blowing pastrami and corned beef atop real rye bread. And, fully they get it here…stay focused on your specialty and forget the rest. In this case, the only other necessary ingredient is stone ground mustard.
That’s it. I had a true New York moment—and, an expensive New York moment. The tab was $50 for two sandwiches and three sodas!
DAY 2—Scott’s Pizza Tour & Chinatown

Our favorite—Lombardi’s Pizza
After eating a super basic self-serve breakfast in Sanctuary’s “dining room,” we set out for our adventure of the day. Not a single complaint exited the kids’ mouths about today’s activity—a pizza tour by Scott’s Pizza Tours.
Scott showed up right on time outside of Gatsby’s, the location of the original Lomardi’s Pizza in Little Italy. He was exactly what I was praying for…funny, dorky, contagiously passionate, and a pizza genius. Here’s a blurb from his website:
“Scott Wiener is a weathered traveler who has searched far and wide for great pizza. He developed a deep appreciation for New York pizza while traveling cross-country, noting both delicious and abysmal pies in his Pizza Journal. While some gems did pop up, nothing quite matched the quality of the pizza back home. Pizza soon became an obsession, as Scott’s beloved Pizza Journal provided empty pages that begged to be filled. The media even took interest and Scott found himself in Las Vegas, judging twenty pizzas for Pizza Today magazine’s International Pizza Expo in 2007. New Jersey’s Garden Plate Magazine says “Call Scott Wiener what you want — crazed, possessed, in serious need of a life — but you have to admire someone who has thrown himself so enthusiastically into his work, his mission.” With this mission clear, Scott has made it his duty to deliver the people to the pizza. Armed with a NYC Sightseeing Guide license and an unstoppable hunger, Scott is ready to share his favorite slices with you.”
Who knew there was so much to know about pizza??? In three hours, our brains—and stomachs—became stuffed. First stop—the “oldest Italian cheese store in America”—Alleva’s. Here we were graced with unsalted fresh mozzarella made less than 30 minutes before we arrived. Just one of countless examples of what New York is all about.
Next stop—the (self-proclaimed) “first pizza parlor in the U.S. We got to sit down at Lombardi’s and eat an entire AMAZING Margherita pizza. Other stops included—1) Joe’s Pizza, a walk-up pizzeria selling slices of pie near NYU, and 2) John’s Pizzeria—the offspring of Lombardi’s opened in 1929, We left qualified enough to conduct our own amateur search for the perfect New York pizza, although we were all doubtful anyone would be able to top Lombardi’s.
I used to cram each and every day of our vacations so full of sight-seeing that everyone [except me] would be pushed to their outermost limit. Not any more and my family is thankful. Every afternoon we headed back to our sanctuary to read, write, get a Facebook fix, Yelp, download pictures…or just snooze.
Since being turned onto Yelp several years ago, the quality of the meals and activities on our vacations has drastically improved. They suggested some fun places to stop during our evening in Chinatown—including Prosperity Dumplings, Chinatown Ice Cream Factory, and Chinatown Fair.
Prosperity Dumplingsis a family-run walk-up counter in an authentic section of Chinatown. Choose your dumplings and sesame pancakes from the menu above your head [yes, the prices ARE in U.S. dollars], wait a few minutes, and smile. How many places in the U.S. can you feed and hydrate a family of four for $11.00??? I slunk away actually feeling guilty we had gotten off so cheap.
Our individual personalities were wildly apparent at the Chinatown Ice Cream Factory. My boy and I had the “When in Chinatown…” mentality and opted for green tea ice cream, while my even-keeled husband and picky pants girl played it safe with chocolate chip and mint chocolate chip, respectively. Every flavor was worth the long wait in line.
Our trip to the Chinatown Fair vintage arcade was really a ploy to use against the kids at tomorrow’s Ground Zero tour. When we walked into a dark and sweltering room filled with sweaty boys and boy-men, I questioned my ability to survive the next 30 minutes. Thank God I found Centipede and Galaga—the only two games I had any hope of surviving longer than 30 seconds. And, then a miracle happened.
My game-aholic son stopped, turned around, and looked at me—”Let’s go, Mom…this place smells of obsession.”
YES!!! This was just the sign of hope this mother needed.
After our Chinatown adventure, the kids were done for the day. I wasn’t. Next adults-only stop—Three of Cups. I had earned my white wine sangria. And, the coal-fired pizza oven behind us did not escape my attention. I feel the competition heating up.
DAY 3—Ground Zero
This morning as I gingerly placed an entire loaf of moldy bread in the “dining room” trash receptacle, I reminded myself how much breakfast money we were banking by eating here.
Today’s itinerary was courtesy of The Cool Parent’s Guide to All of New York—it started with a stroll through Hua Mei Bird Garden in Sara D. Roosevelt Park. The rest of the family may have begged to differ with the whole “cool” thing, but I could have stayed here snapping photos for hours. Elderly Chinese men, prized song birds, and hanging bamboo cages filled with fighting thrushes, finches, canaries, and more—God, I love New York.
In our family, there is a parallel relationship between outside temperatures and bitchiness—at least in the younger generation. I was worried as the temperature climbed as we walked to our walking tour of Ground Zero. The kids took the opportunity to remind me of my “no more food-less tours promise”—and, I assured them, this was a rare exception for good reason. I was seriously counting on the tour guide who was personally impacted by 9/11 to save me.
About 30 minutes after the tour began, I let my breath out. Seriously—everyone just needs to stop questioning my trip planning prowess.
The tour was emotional, educational, AND enlightening. After about 40 minutes perusing the WTC Tribute Center gallery, which houses videos, photos, quotes, paraphernalia found in the wreckage, the walking portion of the tour began. Our guide, Chris, was a middle-aged guy who had been working on the 82nd floor of the first building to be hit. As he told the harrowing story of his narrow—and very lucky—escape, he choked up multiple times. For once, I was not the only one who couldn’t hold back empathy tears. My kids voluntarily admitted that I had, indeed, picked an “awesome” tour.
Emotionally spent and getter hotter by the minute, it was only the promise of crepes that kept the kids walking. It was four blocks to the 5-star rated Crepes du Nord, where we gorged on crepes filled with chicken/goat cheese/asparagus, prosciutto de parma/arugula/ricotta cheese, and raspberries/Nutella/fresh whipped cream, all washed down with house made lingonberry soda. The people got it right once again.
For dinner we officially entered Three of Cups into the family pizza competition. Their Margherita pizza shot straight to second place—coming close to knocking Lombardi’s down from their first place spot.
After dinner, we hopped onto the subway toward Times Square to see a kid-friendly improv comedy show at Chicago City Limits. We could still chuckle over the skits we saw here several years ago. The show’s formula doesn’t change, but the talent and audience does making it a different experience each time you go.
DAY 4—Greenwich Village
The city was like a giant oven on our country’s 234th birthday. In fact, it decided to set a record for the highest July 4th temps since 1973. Lucky us.
After breakfast, the kids went on strike, refusing to stray more than four feet from the air conditioner. Thank God for cell phones. We adults headed out to explore the quiet brownstone-lined streets of Greenwich Village. I wanted to take my husband to the places I had so enjoyed on a my previous gluttonous wander here—Murray’s Cheese, Palma Restaurant, Milk & Cookies, and Cherry Lane Theater.
We stumbled upon a recommended restaurant just in time for lunch. The Little Owl is a teensy neighborhood eatery on Bedford Street, my favorite street in the Village. Our scrumptious lunch included fresh tomato salad with house made ranch dressing and gravy bangers served on cheese-encrusted mini-buns. I later found out that it’s not uncommon to wait two hours to eat lunch here.
That afternoon, I got a message from a local Yelper who suggested several pizzerias to include in our competition. For tonight’s dinner we chose Pizza Gruppo in Alphabet City, a tiny hole-in-the-wall specializing in ultra thin crust pizza. If you like your pizza to have some substance, you probably won’t be a huge fan of this place. Our family gave it mixed reviews putting it in solid third place (tied with Joe’s Pizza).
I blame today’s horrible decision on laziness brought on by high temps. Taking the advice of Mario, the manager of Sanctuary, goes on record as one my worst decisions. Rather than head to Williamsburg to watch the Macy’s firework show like my travel book recommended, I believed Mario when he assured me we would be able to see the 40,000 shells launched in honor of our country’s birthday from Sanctuary’s roof deck.
YOU ARE WRONG, Mario—you see smoke while hearing every shell you’re missing. I worked hard to let it go for Mario’s sake.
DAY 5—Japanese Tea, Vintage Candy & Bryant Park
Rising outside temps had the kids fiercely protecting their energy. It was only the promise of ice cold tea and rice balls that lured them out of their sanctuary.
Yaya Tea Garden was not a place we would have found had it not been for Yelp. Definitely a local hangout, it serves up Japanese sodas and fruit-infused iced teas. None of us were brave enough to try the “gel” additive, which had been not so appetizingly described as “similar to Jello.” Maybe next time. Despite warnings and instructions by previous Yelpers, we failed the rice ball IQ test.
The promise of candy was the next lure. We took our time getting to Economy Candy in the Bargain District. Both kids remember this place from their visit several years ago and my girl was thrilled to rid herself of regret and get the rainbow colored licorice strings. I got adventurous—violet pastilles, a chocolate covered sesame bar, Zotz, and sour cherry gum. My husband got his usual malted milk balls.
The sign of a stellar restaurant is one that can lure me back for a second—and almost unheard of third—visit on a single trip. On this trip, Three of Cups earned that rare distinction. It also helped put my kids in the right frame of attitude to hop on the underground sauna (AKA…subway) and sweat on the grass while watching “The French Connection” at Bryant Park. Being fans of fresh air and not so much of old movies, we snuck out about halfway through and went in search of water.
DAY 6—Shopping, Eating & the Theater
Visiting New York City with teens in the middle of summer came about for a reason—my husband had to work. While he attended meetings this morning, the kids and I successfully navigated our way to the Apple Store on 5th Avenue. Not that much different our San Diego store, we didn’t linger long in favor of FAO Schwartz next door. We were all stunned by the endless toys, some priced as high as used cars.
I was beside myself with anticipation to introduce my kids to one of my favorite places on the planet. I prepared them for the melt-in-your-mouth dumplings at Radiance Tea House. I knew my boy got it when he said—“Oh my God, I’d move here just to be able to eat here.”
After an afternoon rest, my husband and I braved the heat and walked the few blocks to Pommes Frittes, home of authentic Belgian fries and the delectable dipping sauces to compliment them. Oh, my.
Going to New York City with teens earns parents some adults-only time—we began ours with a heavenly dinner at Palma Restaurant, followed by an off-off-Broadway comedy production at Cherry Lane Theater. It was exactly what we needed.
DAY 7—Movie & Pizza
Another day of meetings for the husband—another day of navigating the subway for the rest of us. Today my boy proved that he really is paying attention when he navigated us to Battery Park into an air-conditioned movie theater and another pizza contender.
Tucked inside a pedestrian alley, Adrienne’s Pizza Bar was the temporary home of the World Cup enthusiasts in the immediate vicinity. It’s possible the broken air conditioner was behind our so-so experience here [and the less than so-so service], but none of us could get behind the rectangle pizza with fluffy crust.
We nearly melted in the subway going back to our room. Triple-digit temps and close quarters were taking their toll on all of us. It was definitely ironic that I found myself heading outside for a walk to cool down.
DAY 8—Going Home
We survived our wander to New York City with teens! This is a city with a vibrant history and international flavor that is home to a diverse population—many who hold tight to their ethnicity and the art of the specialty. It’s artistic and intellectual. My spirit thrives here. But, damn, New York City is sweltering in July.
Did you ever figure out how to “properly” eat a rice ball? 🙂
I remain ‘rice ball challenged’ to this day. 😉 Happy travels!