When your kid gets the chance to study abroad, you know it’s one of those once-in-a-lifetime opportunities — the kind that shapes who they are, far beyond the classroom.

So when Greg came to us with an international business program in Paderno del Grappa, Italy, it wasn’t a hard sell. He was excited, motivated, and ready to go. Still, as a parent, there’s always that moment of hesitation — the one where you weigh dreams against dollars. Encouraging your kids to see the world is one thing. Making it happen financially is another.

In the end, we pulled it together. And I’m so glad we did. Sure, Greg had his fair share of pub crawls and pizza nights, but he also came back with a broader view of the world — and of himself.

At the end of the program, Clare, Julie and I flew over to meet him. What started as a way to “retrieve” Greg turned into a slow, unforgettable two-week trip through northern Italy. We kicked things off in a quiet little hotel just outside Paderno, soaking in the local charm before heading out to explore the region together.

In this blog, you’ll get a glimpse of what that journey looked like — the moments that made us laugh, the places that made us pause, and how one college program ended up giving our whole family something to remember.

The scenery was magnificent and our trip was off to a great start.

Our first stop? Marostica.

It’s a beautifully preserved old town, the kind that feels like it should only exist in films or postcards. Stone battlements still frame the town, a reminder of its medieval past. And what makes Marostica famous is something pretty unique — every two years, they play a human chess game in the main square, complete with knights, nobles, and life-size pieces dressed in full costume.

While we didn’t catch the chess match (it wasn’t the right year), just being in that town felt like stepping into a storybook. Wandering the cobbled streets, peeking into cafés, looking up at the hilltop castle — it was the perfect way to ease into Italy and into this rare window of time we had together, just the four of us.

By the time we arrived in Italy, Greg had already spent weeks soaking up the local culture — and not just through textbooks.

He’d learned the rhythms of small-town Italian life, picked up bits of the language, and figured out which cafés had the best espresso. So when we started travelling together, he naturally stepped into the role of tour guide.

Our next stop after Marostica was Asolo, a nearby hilltop town often called “the pearl of the province.” It’s known for its winding stone lanes, sweeping views, and quiet elegance — the kind of place you might miss if you didn’t know where to look. But Greg knew. He led the way up the narrow roads, pointed out historical spots we’d have otherwise walked right past, and even recommended where we should stop for lunch.

It was a shift — subtle, but special. The same kid we’d dropped off weeks earlier was now steering us through Italy with confidence. You don’t always see personal growth in big, dramatic moments. Sometimes it’s in the way someone orders food without hesitation, or how they navigate a train schedule in another language.

Greg’s time in the program had clearly taught him a lot — and not just about business. It had given him context, curiosity, and confidence. And for us, as parents, seeing that was as rewarding as the trip itself.

There was always time to find a vineyard and do a tasting before going to another site.

One of the best parts about traveling together as a family is how everyone brings something different to the table. For us, it turned into a kind of shared treasure hunt — where each of us uncovered something unexpected that made the trip unforgettable.

For me, one of those surprises came from a place I’d completely forgotten about — until the internet jogged my memory. It’s called the Tempio Canoviano, or Temple of Canova, a hilltop church in Possagno. It’s not on the usual tourist route, but it’s an absolute marvel.

Built in a severe Neoclassical style, the temple was designed by Antonio Canova himself — yes, the sculptor — and finished after his death. The symmetry, the scale, the silence inside… it stopped me in my tracks. There’s something about standing in a place like that, knowing it was imagined centuries ago and still towers above the hills, that just gets under your skin.

And then — Venice.

What can you even say about Venice that hasn’t been said already? It’s surreal. The canals, the crumbling facades, the gondolas gliding silently under stone bridges — it all feels like a dream someone forgot to wake up from. You turn a corner and suddenly you’re in a wide-open piazza with a violinist playing under a colonnade. And you think: Yeah, I get it now.

If I ever get the chance to go back, I’m there. No hesitation. It’s the kind of place that seduces you quietly, then doesn’t let go.

For all the ground we covered, what really made the highlights shine wasn’t just the places — it was sharing them. Watching Julie light up over gelato, seeing Greg explain the quirks of Italian train stations like a local, or sitting with Clare at a café while the world passed by — those were the real keepsakes.

While in Venice, you have to go on a gondola ride, it’s mandatory.

Stopping in for a libation after the gondola was a must.

I want that yacht.

We even took a trip out to Murano to see the famous Murano glass being made — which, by the way, is like watching fire and colour dance together. Just getting there was an experience. Imagine standing at what’s essentially a bus stop in Venice… except the “bus” is a boat. You’re surrounded by water on all sides, waiting to float off to the next island like it’s completely normal. It’s one of those things that only sinks in when you pause for a second — We’re on a boat. This is the bus.

If I ever get the chance to go back to Venice, I’m there. No hesitation. It’s the kind of place that seduces you quietly, then doesn’t let go.

Back in Venice, we climbed St Mark’s Campanile, the iconic bell tower that watches over Piazza San Marco. The views from the top are absolutely spectacular — rooftops, canals, the lagoon stretching out in every direction. But let me tell you, if you happen to be up there when the bells ring… bring earplugs. They are deafening. We were laughing and half-covering our ears, caught between awe and “How fast can we get back down?”

And sometimes, in the middle of the trip you find yourself standing in Venice — surrounded by canals and ancient buildings, gondolas gliding by — and you just can’t get over it. The scenery. The stillness. The sheer magic of it all. You look around, and it feels like the world is giving you a moment to remember.

By the time we reached Verona, our trip had started to take on a slower rhythm. The rush of arrivals and train schedules had given way to something more relaxed — the kind of travel where you spend less time checking your watch and more time simply looking around.

Verona felt like the right place for that.

It’s a city with history woven into every stone — Roman arenas, medieval piazzas, Renaissance buildings that lean gently into one another. But it never felt crowded or overwhelming. Instead, Verona invites you to slow down. To walk the bridges, sit in the piazzas, and let the city unfold at its own pace.

Since it was on the tour, of course we had to visit Juliet’s house. Or rather, Juliet’s home. You know the one — with the little balcony and the statue in the courtyard. It’s pure tourist bait, but we embraced it. There’s something oddly charming about seeing people leave love letters on the wall or rubbing the statue’s bronze for luck in romance. It may not be Shakespearean fact, but it’s become part of the city’s story — and part of ours, too.

We also made a stop at the Arena di Verona, one of the best-preserved Roman amphitheatres in the world. Walking into that open-air arena and imagining it filled with the sound of opera under the stars… it gives you goosebumps. Verona has a quieter kind of magic — one that doesn’t demand attention but lingers long after you’ve left.

And yes, Verona has a Roman Arena — one of the best-preserved in the world. Walking into that open-air amphitheatre, you can almost hear the sound of music echoing through the stone. They still hold performances there, and just standing inside makes you feel like you’ve stepped into another era.

As we made our way through the region, we carved out time for a stop in Bassano del Grappa — a town that wears its name with pride and flavour.

Naturally, we had to try the grappa.

For the uninitiated, grappa is not your average after-dinner drink. It’s made by distilling the leftover skins, seeds, pulp, and stems from winemaking — a sort of no-waste spirit with roots deep in Italian tradition. It’s clear, strong, and sharp enough to catch you off guard if you’re not ready. The alcohol content can reach as high as 60%, and trust me, it tastes every bit of it.

Legend has it that grappa was first created right here in Bassano del Grappa by a Roman soldier, who somehow figured out how to turn winemaking scraps into liquid fire. Whether or not that’s true, the town embraces the story, and the drink, with open arms.

We sipped ours slowly — or at least tried to. It’s the kind of drink that goes straight to your chest, making you blink a few extra times and wonder if you’re breathing fire. But as far as cultural experiences go, it’s unforgettable. It’s bold, a bit wild, and very, very Italian.

The town itself is picturesque and peaceful, with a famous wooden bridge, riverside charm, and fewer tourists than other stops. But make no mistake — if you visit, the grappa is the headline act.

Next on our whirlwind tour was Florence — a city that feels like it was built to be admired. While others may be drawn to the grand cathedrals and Renaissance art, I found myself captivated by the ironwork and windows. The small details. The way sunlight hits an old wrought-iron balcony, or how a crooked window frame tells a story all its own.

I tried to capture Florence not just through the big, bold landmarks — but through the quiet craftsmanship that holds the city together.

But there’s far too much of Florence to take in just through gaps in ironwork and windows. The city demands your full attention — from every angle.

Take the statues, for instance. They’re everywhere — standing proudly in piazzas, tucked into corners, watching from high above. Most are real, centuries-old masterpieces. But a few? Not quite. Some are replicas, filling in for the originals that now live safely behind museum walls.

It becomes a bit of a game: Can you spot the fakes?

Florence’s Duomo, officially known as the Cattedrale di Santa Maria del Fiore, is an awe-inspiring masterpiece of Gothic architecture. Its terracotta-tiled dome, a marvel of engineering by Brunelleschi, and Giotto’s elegant bell tower are truly unforgettable.

Other scenes around the Florence were often spectacular.

If you get lucky, there will be some type of celebration.  While we were there, they had a fireworks display one evening and a parade.

We did have a chance to take a bus over to Siena, one of Florence’s rivals.  The two cities fought for years and Siena was defeated by Florence in alliance with the Spanish crown in 1555 during the Italian War of 1551-59.  According to legend, Siena was founded by Senius and Aschius, two sons of Remus. Supposedly after their father’s murder by Romulus, they fled Rome, taking the statue of the she-wolf suckling the infants, which became the symbol Siena.

The Siena Cathedral, a breathtaking example of Italian Romanesque-Gothic architecture, captivates with its striking black and white striped facade, completed in 1380. While the origin of this unique design remains uncertain, one intriguing possibility links it to the legend of Senius and Aschius, whose white and black horses are said to have inspired Siena’s coat of arms, the Balzana.