What We Learn When We Travel Together—Across Generations
We just returned from a family trip to New York. My Italian mother-in-law (MIL) recently turned 80, and it had always been her dream to visit the concrete jungle where dreams are made. She wanted it to be a family trip, so we made it happen.
We were a group of seven: three teenagers, three midlifers, and my MIL—ages from 13 to 80.
One of my MIL’s requests was to visit Ellis Island, drawn to its history—the gateway through which 12 million immigrants entered America, 4.5 million of them Italians seeking a better life.
On our way to JFK, she shared her own family’s immigration story: her grandmother’s brother left Italy for Argentina with his four children, hoping for a better future. Her grandmother, in turn, had been encouraged to marry a man of standing to fund her brother’s passage. Letters were exchanged for a few years, then contact was lost.
This sparked an animated taxi debate:
“We should write to that TV show that finds missing family members!”
“We can get our money back!”
We laughed, fully engaged in the subject all the way to the airport.
At Ellis Island, the museum told an honest, matter-of-fact story. Unsmiling faces stared back from black-and-white photographs. Audio recordings spoke of uncertainty, fear, the chaos of 5,000 people packed into the Grand Entry Hall, different languages rising and falling.
Medical inspections determined fates with a poke, a prod, and a chalk mark on the sleeve: entry, quarantine, or deportation. Entire ships arrived carrying only single women, who, by law, couldn’t enter unless a husband or family member awaited them.
What became of them?
My MIL said that the photos gave her “angoscia”—anxiety. Maybe she was thinking of the family lost to Argentina. I couldn’t ignore the irony of standing in Ellis Island in 2025, where immigration once followed a flawed but structured process, while outside, America grapples with chaotic, indiscriminate deportations.
Ellis Island was grueling and bureaucratic, but it had some safety nets, and pathways—it was also over 100 years ago.
The next evening, we took an Uber to dinner. A small black Tesla pulled up, driven by a smartly dressed blonde woman, maybe in her 50s.
“I do this in the evenings from 6-9pm,” she said. “I’m funding my son through college. My day job is in sales.”
Originally from the Dominican Republic, she smiled. “I’ve been a New Yorker for 30 years.”
She was friendly, bright, upbeat—proud.
As we said goodbye, my SIL remarked, “That is the true spirit of America right there.”
I agreed. She embodied entrepreneurship, strength, work ethic, positivity—the original American Dream.
But does the world still value that determination? On Ellis Island, immigrants had to prove their worth before stepping onto American soil. Today, countless prove themselves daily.
My MIL’s story, Ellis Island, and our Uber driver all highlight resilience and reinvention. But are we, as a society, still fostering opportunity, regardless of age, background, or journey? Are we prioritizing meaningful shared experiences across generations?
Our New York trip was also a reminder of how precious time together is. Seven of us, aged 13 to 80, created moments that will stay with us long after our return to Italy—history, laughter, discovery, connection. The things that make life rich.
In 100 years, how will history judge today’s world? Will we have nurtured a society that values contribution at every stage of life? Will families still carve out time for one another, deepening connections across generations?
I hope so. Because in the end, these are the moments that shape us, history, and the future. The ones that endure and matter.
-Emma
Emma Cuthbertson is a digital marketing consultant based in Northern Italy. Originally from Cornwall in the UK, she has spent much of her life mastering the art of embracing change—from living and working across Europe, raising her family, changing career in her 40’s – and mostly discovering that resilience pairs beautifully with a good sense of humor. Emma is also an active community member of the MEA. About to turn 50, life threw Emma an unexpected detour. She shares her reflections on resilience, adaptability, and finding a new way forward in midlife. https://substack.com/@fromthemessymiddle