When we asked our 13-year-old granddaughter if she would like to take a trip with us, we were expecting an immediate and enthusiastic “Yes!” Instead, she responded with thoughtful consideration, wondering how a trip might fit into her existing school and extracurricular commitments.

That moment alone told us something important—she was growing up. Once we reassured her that the timing of a trip would be completely flexible, the excitement began to build.

We presented her with three destination choices and tentative itineraries for each —Washington D.C., Chicago, or New York City. Not surprisingly, she picked the most dynamic of them all: New York City.

Traveling with a Teen

From the very start, it was clear we were in for an incredible experience. Our granddaughter was an absolute delight—naturally intuitive and confident in every situation. She handled air travel, subway lines, and crowded streets with ease, never once appearing overwhelmed. She kept a watchful eye on Granddaddy forging ahead, and on me, always bringing up the rear. The only time she voiced concern was when she thought I needed to catch up. Thirteen turned out to be a perfect age for travel!

With three days to explore the city, here is how we made the most of it.

Day One: Lady Liberty & Midtown

• 10:00 AM – Arrived at our Midtown hotel and stored our luggage
• Took the subway to Battery Park to kick off our adventure
• Boarded a Statue City Cruise to the Statue of Liberty using pre-purchased tickets for viewing from pedestal only (departing from Castle Clinton)
• Strolled through Battery Park and visited the whimsical Sea Glass Carousel
• Enjoyed a late lunch/early dinner at Fraunces Tavern, a historic and cozy spot (reservations recommended)
• Took the subway back to the hotel to check in and unpack
• Headed to Rockefeller Center to view the city from the Top of the Rock (pre-purchased tickets)
• Visited the FAO Schwarz Toy Store and Aritzia (she loved them both!)
• Explored St. Patrick’s Cathedral with its stunning architecture, both inside and out
• Snacked on iconic New York street food before calling it a night

Highlight of the Day: Seeing her face light up as the Statue of Liberty came into view.

Day Two: Bridges, 9/11 & City Lights

• Took the subway to Pier 11, then hopped on the East River Ferry to DUMBO
• Walked across the iconic Brooklyn Bridge back into Manhattan
• Visited Trinity Church and its historic cemetery
• Explored The Oculus, then grabbed lunch inside the airy, modern space
• Spent time at the 9/11 Memorial—a moving experience for us all, and viewed One World Observatory
• Went to Brookfield Place for shopping (Lululemon and others—she couldn’t wait!)
• Took the subway to Times Square, the departure point for our pre-booked “New York City at Night” Bus Tour from 5:30–10:00 PM, including the High Line, Little Island, view of the Skyline from Pier 17, the lights on Manhattan and Brooklyn Bridges, Grand Central Terminal, and authentic NY Pizza from Little Italy Pizzeria. (It rained on us briefly while on tour, but we didn’t care!) We returned to our starting point near Times Square.
• Took a taxi back to the hotel, tired but so impressed with the city

Highlight of the Day: Walking the Brooklyn Bridge together and soaking in the skyline.

Day Three: Park, Broadway & Times Square

• Caught a bus to The Metropolitan Museum of Art, then walked through the center of Central Park:
  • Belvedere Castle, Swedish Cottage, Shakespeare’s Garden, Bow Bridge, Bethesda Fountain, The Lake
• Circled back to The Met and visited the lobby only
• Enjoyed a family-style Italian lunch at Tony’s Di Napoli
• Back to the hotel via subway to freshen up for our Broadway afternoon
• Attended a 3:00 PM performance of “Wicked” at the Gershwin Theater
• Capped it all off with dinner, another walk through Times Square (her favorite) and a visit to the M&M’s Store

Highlight of the Day: Sensing her anticipation as we waited for “Wicked” to start, and watching the “little girl” in her make personalized M&M’s at the M&M’s store.

Leaving for Home

Before heading to the airport, we had just enough time for a quick walk through China Town and Little Italy where we bought matching T-shits. We said goodbye to the city with full hearts, tired feet, and countless memories. As we headed home, we reflected on what made this trip so amazing. Yes, New York is unforgettable—but showing it to someone special makes it magical.

Final Thoughts

Traveling with a teenager can be unpredictable, but we were blessed. Our granddaughter’s poise, wonder, and warmth turned this into one of the most joyful trips we’ve ever taken. She had a smile on her face constantly and she reminded us to always go with the flow, stay curious, and savor the moment.

If you’re considering a trip with your grandchild, we highly recommend it. And if you’re headed to New York City, don’t worry about trying to “do it all.” It isn’t about what you see, it’s who you share the memories with.

PS: We are hoping to do a similar trip somewhere with our grandson in a couple years. Fingers crossed!