How my family aced our first-time trip to New York City

Thousands of steps, music history and a Dylanesque sighting made up an immersive first-time visit to NYC.

By Amy Carlson Gustafson

For the Minnesota Star Tribune
April 26, 2024 at 12:50PM
A view of Manhattan from the 86th-floor observation deck of the Empire State Building on a cloudy March afternoon. (Amy Carlson Gustafson/For the Minnesota Star Tribune)

As we were preparing to land at LaGuardia, I gasped as my smile grew. The monumental Manhattan skyline I’d seen thousands of times on TV, in movies and photos was genuinely awe-inspiring. Filled with anticipation and a bit of panic, I could hardly wait to set foot in New York City for the first time.

“What? Really?” Without fail, that was the response when I told people I’d never been to NYC. Confession: I had long been obsessed with America’s largest city, but also had found it incredibly intimidating. Would I be able to walk fast enough? (Yes.) Would my family get lost? (Just a couple of times.) Would I look like an unstylish, overwhelmed tourist? (Totally.) Did any of that matter during our nine-day trip in March? (Nope.)

But when my 12-year-old son, Charlie, suggested NYC for spring break, my first reaction was a definitive “no.” Striking the right balance of experiences for my husband and me, as well as activities and sights to keep the kid interested, felt overwhelming.

On the other hand, I realized that family travel experiences are more important than my hangups. So I took the plunge, booked a flight, found a hotel in Manhattan (the stylish Kimpton Hotel Eventi in Chelsea, via Costco Travel), and cobbled together a semi-flexible itinerary, with a little something for everyone.

Little did I know, I’d even have a Bob Dylan-related celebrity spotting.

First impressions

  • I was pleasantly surprised by how friendly New Yorkers are. When I mentioned that to an off-duty firefighter who struck up a conversation with us at a bar in the Meatpacking District, he joked, “Don’t tell anyone.”
  • The breathtaking view from the 102nd floor of the Empire State Building was worth the cost.
  • While Charlie was on the edge of his seat for a New York Knicks vs. Brooklyn Nets game at Madison Square Garden, for me the best part was watching Knicks superfan Spike Lee’s animated reactions from his courtside seat.
  • The 9/11 Memorial & Museum was a somber yet rich experience. We appreciated the outdoor tour, where guide Emmeline Prior did an impressive job balancing history and stories with details surrounding the tragedy.
  • Broadway did not disappoint, either. We saw two musicals: a preview of “The Outsiders,” a compelling adaptation of S.E. Hinton’s classic coming-of-age novel and the 1983 film featuring a cast of talented newcomers; and the hilarious “Little Shop of Horrors” off-Broadway, starring Evan Rachel Wood and Darren Criss.

By foot, car, subway, ferry or tram

It turns out that we’d been training 30 years for New York thanks to the Minnesota State Fair, where our family honed our expert crowd navigation skills that would come in handy on the bustling NYC streets — especially the crowded Brooklyn Bridge.

We walked tens of thousands of steps in NYC. Unfortunately, the first couple of days, it rained hard, prompting us to use ridesharing apps. But once we purchased our $34 MetroCards and tested our subway skills on our third day in town, it became second nature as we ventured all over Manhattan, Queens and Brooklyn.

We relied on the free Staten Island Ferry for a close look at the Statue of Liberty. For the best views, snag a seat on the right side when you board the boat and switch to the left for the return ride.

We rode the fun but crowded Roosevelt Island Tramway over the East River to explore the serene Franklin D. Roosevelt Four Freedoms State Park and the ruins of the historic Smallpox Hospital. I had to bribe the kid with a treat from Anita La Mamma del Gelato for this stop. However, he became engaged when we discovered a bunch of cats lounging around at the nearby outdoor cat sanctuary run by the Wildlife Freedom Foundation.

Captivating tours

At the suggestion of my nephew’s wife, we sought out a food tour in Jackson Heights, Queens. The minute we stepped out of the subway into the vibrant, densely packed neighborhood, the aromas and sights were a party for the senses. We joined Laura Siciliano-Rosen from Eat Your World, who guided us through a feast of savory and sweet cuisine from Bangladesh, Tibet, Nepal and Colombia. Standouts included a variety of momos (steamed dumplings), samay baji with goat suki (a bento box of snacks with dried goat meat) and chola bhuna (a Bangladeshi black chickpeas-potato dish commonly served during Ramadan). My son didn’t love everything, but tried most of it and enjoyed the goat suki.

We also ventured to Harlem for a tour of the legendary Apollo Theater. Mr. Apollo himself, Billy Mitchell, featured in the HBO documentary “The Apollo,” dazzled us with stories about seeing everyone from James Brown to H.E.R. for the first time at the theater. Mitchell’s charisma and historical knowledge made for an engaging tour with a mock “Amateur Night,” where our tourmates impressed us with their talents. Bonus: “The Harlem Renaissance and Transatlantic Modernism” exhibit at the Metropolitan Museum of Art (running through July 28) was a fine complement to the tour.

My husband and I had our hearts set on the “Birth of Punk” tour led by historian, author and musician Jesse Rifkin, of Walk on the Wild Side Tours NYC. The kid? He was happy to chill at the hotel while we splurged on a private tour. Beginning in Greenwich Village, the fascinating journey had surprises around every corner, whether it was Rifkin pointing out the loft where Kiss played their first Manhattan show opening for transgender punk icon Jayne County, standing in the spot where the Ramones posed for the “Rocket to Russia” album cover or studying the building where the Velvet Underground first met Andy Warhol and Nico.

Another night, I had a different kind of musical encounter. While my son and husband ventured off for barbecue in Koreatown, I met my NYC friend Brad at the kitschy Trailer Park Lounge. Leaving the dive bar, we noticed several vintage cars and a production crew set up by the Hotel Chelsea.

Turns out they were filming “A Complete Unknown,” the new Bob Dylan biopic. I caught a brief glimpse of Timothée Chalamet, who plays Dylan, then watched them shoot a scene where Joan Baez, played by Monica Barbaro, attempts to hail a taxi. I even got scolded by a crew member for standing in the wrong place.

That quintessential New York moment was a great reminder to be open to the unexpected. In NYC, the next great experience could be right around the corner.

Amy Carlson Gustafson is a Twin Cities-based journalist.

A busy pedestrian walkway on the Brooklyn Bridge in New York, on a sunny Sunday afternoon in March. (Amy Carlson Gustafson/For the Minnesota Star Tribune)
The ruin of the Smallpox Hospital on New York City's Roosevelt Island was listed on the National Register of Historic Places in 1972. (Amy Carlson Gustafson/For the Minnesota Star Tribune)
Historian Billy Mitchell, aka Mr. Apollo, entertains a tour group with his stories of legendary musicians who performed at the world-famous Apollo Theater. (Amy Carlson Gustafson/For the Minnesota Star Tribune)
A night shoot of Bob Dylan biopic "A Complete Unknown," starring Timothee Chalamet, outside the Hotel Chelsea in Manhattan. (Amy Carlson Gustafson/For the Minnesota Star Tribune)
about the writer

about the writer

Amy Carlson Gustafson