From the Colosseum to the Canals: A Family’s Italian Adventure

Christie Costello
1 day ago
5 min read

Some trips are about seeing the world. Others are about sharing it with the people you love.

“...many people have asked and I absolutely cannot take credit for planning this trip. All credit goes to the travel wizard herself, Christie Costello, for planning it all.”

Aubrey shared that on her Instagram after returning home, and while I’m incredibly grateful for the kind words, what stood out even more to me was what this trip represented for her family.

This wasn’t just a vacation. Aubrey was traveling with her two young sons and her parents, bringing three generations together for a shared experience in Italy. From the beginning, she wanted it to be meaningful. Not rushed, not overwhelming, but full of the moments that matter.

One thing she shared early on stayed with me. She really wanted her family to experience Rome. To stand in those places you hear about your whole life and feel it for yourself.

And along the way, something even more special unfolded. What started as a family trip became an opportunity for her dad to reconnect with family he had not seen in a long time.

From Rome to Cinque Terre to Venice, this journey became more than a trip. It became a collection of shared moments, meaningful connections, and memories they will carry with them for years.

Rome: Standing Inside the Stories We’ve All Heard

Rome has a way of making everything feel bigger. The history, the architecture, and the feeling of walking through places you have heard about your whole life.

Aubrey’s family stepped right into that.

They explored the Vatican and St. Peter’s Basilica, taking in the beauty and significance of a place that has shaped centuries of history. One of the most meaningful moments of their time in Rome was attending Mass at St. Peter’s Basilica, something that stood out as a special experience for their family.

Rome also became the setting for something deeply meaningful for Aubrey’s family.

Her dad, one of fifteen siblings, had not seen some of his family in quite some time. While they were in Rome, his youngest sister traveled from Spain with her daughter to surprise him.

What unfolded was more than just a visit. It was a long-awaited reunion in the middle of one of the most iconic cities in the world. They spent time together, catching up and sharing the experience of Rome as a family.

It was one of those moments that no itinerary can truly plan, but ends up becoming one of the most meaningful parts of the entire trip.

Aubrey's boys had their own highlight in Rome too. They especially enjoyed the Colosseum and Ancient Rome tour, where everything started to come to life in a way that felt exciting and real.

Three people stand smiling in front of the Colosseum in Rome. The sky is clear and the background includes trees and stone pathways.

“They actually really enjoyed it. It was like, ‘Wow… I just learned this in school!'”

Another memorable experience was visiting the Roman catacombs and Capuchin crypt. Walking through the underground tunnels gave the boys a completely different perspective on history.

At one point, Matthias looked around at the bones and asked:

“These were real people?”

Aubrey also shared a meaningful Filipino tradition called pagpag, where after visiting places connected to the dead, you stop somewhere before going back home. It is a way of “cleaning it off” before returning to where you stay.

It was one of those moments where travel becomes more than sightseeing. It becomes a sharing of stories, cultures, and perspectives.

Three people pose smiling in front of the Leaning Tower of Pisa on a sunny day with a blue sky and clouds.

Pisa: A Simple, Classic Stop

On their way north, Aubrey’s family stopped in Pisa to see the Leaning Tower. It was exactly what it needed to be. A quick stop, a few photos, and a chance to see one of Italy’s most recognizable landmarks before continuing the journey.

Sometimes that is all it takes.

Cinque Terre: Time Together by the Sea

Cinque Terre was one of the places Aubrey really loved during the trip.

While they were there, the family decided to take a boat tour together. Because of the weather and sea conditions that day, they were not able to go out into open water for the full Cinque Terre route. Instead, they chose a smaller tour closer to shore and enjoyed the experience as a family.

Three women in swimsuits and hats pose smiling under red-striped umbrellas at a sunny beach resort, with a vibrant yellow building behind.

Sometimes travel works out that way. Plans shift a little, but the time together becomes the part everyone remembers most.

Venice: A Favorite Stop on the Journey

Venice turned out to be one of Aubrey’s favorite places on the trip, and the boys loved it too. The canals, historic buildings, and slower pace gave the city a completely different feel from the other places they visited.

During their time there, the family had an unexpected experience. After taking the water shuttle into the city from their hotel, they were offered a free ride to Burano, one of the nearby islands. They decided to go, and it ended up being a memorable part of their trip.

a woman with two young boys poses i front of a canal in venice, italy — *Aubrey & her boys*

While in Burano, they visited a glass factory where they watched artisans create beautiful glass pieces. Aubrey’s mom especially loved it and ended up buying a glass horse to bring home.

Venice was also where Aubrey really enjoyed the seafood, which stood out as a highlight during their time there.

And of course, while they were there, she made sure to experience a gondola ride through the canals. One of those classic moments that simply feels right when you are in Venice.

What Made the Trip Easier

When we talked after the trip, I asked Aubrey what helped the most. Her answer was simple.

“It’s the organization of everything. You took care of every little thing. The trains, the tours… I wouldn’t even know where to start...I’ve planned many trips before, but I could not do that for a whole family. I just couldn’t.”

Planning a trip for an entire family across multiple cities is not simple. Hearing her appreciation of that meant a lot to me. I told Aubrey how grateful I was to be a small part of their adventure. It really was such a joy to help bring this trip together.

And before we even finished our debrief conversation, she was already thinking about the next adventure.

Why Trips Like This Matter

Trips like Aubrey’s are never just about the destinations.

They are about watching your kids connect what they are learning to the world around them.
They are about sharing meaningful moments like Mass in St. Peter’s Basilica.
They are about unexpected reunions with family in the middle of Rome.
They are about being together in a place you will always remember.

Those are the moments that stay.

Thinking About Your Own Italian Adventure?

If Italy has been on your heart, I would love to help you create something just as meaningful for your family.

Trips like this work best when the details are thoughtfully organized so you can stay present in the experience. You get to enjoy the moments, the connection, and the memories without carrying the weight of managing every piece along the way.

Italian Adventure