Our first family visit to Italy was ten years ago now.  Italy was at the very top of my bucket list — and it did not disappoint. It immediately spoke to us, and we fell deeply in love.

We began in Rome — overwhelmed in the best possible way.

Ancient ruins. Crowded piazzas. Fountains tucked around corners. Rome is a lot. And we loved it.

There is an energy in Rome that can't be missed. It is vibrant but welcoming .  Our days were filled with wandering ancient streets, stopping for gelato — or a “Gelato Perroni,” as Andrew once called his Dads beer. Afternoons were spent leisurely drinking some of the best wine we have ever experienced while watching life pass us by in Piazza Navona.

I had booked a “Skip the Line” tour of the Vatican. We arrived at 7:00 a.m., only to wait over an hour to seemingly join the “skip-the-line” line. With temperatures rising close to 40°C and little shade from the relentless sun, we made the difficult decision to cut our losses and head for breakfast instead. We regret missing the opportunity — but in that moment, it was absolutely the right call.

From Rome, we rented a car and drove into Tuscany.

We spent five magical nights in a two-bedroom villa at Castello Poggiarello — a 15th-century fortified organic vineyard near Sovicille. Our villa had a full kitchen and outdoor terrace overlooking the countryside. The grounds were unreal. Wandering the estate, we discovered a Renaissance chapel, a 17th-century villa, and an ancient tower.  If you ever stay there, book the wine tasting. Honestly — one of the best we’ve experienced.

Our days followed a rhythm that felt like a dream.  Mornings exploring nearby towns such as San Gimignano,
Siena and Volterra with their cobblestone streets, medieval towers and espresso stops in tiny cafés. We would make stops at local grocers to gather fresh bread, cheese, produce, and wine for the day.  We were then able to have slower afternoons in our villa enjoying wine by the estate pool and long, relaxed meals on our terrace as the Tuscan sunset cast its golden glow over the hills.  These were the moments that reflected the Italy we had imagined.

From Tuscany, we made our way to Monterosso al Mare in Cinque Terre — but not without stopping for the mandatory photo holding up the Leaning Tower of Pisa.

Driving into Cinque Terre quite literally took our breath away. It was stunning — colourful houses clinging to cliffs, the sea stretching endlessly below.  But if we’re honest, it wasn’t the perfect fit for our family at that stage — and it’s somewhere we absolutely need to revisit.  Hiking from town to town is one of the signature experiences in Cinque Terre. At the time, some of the trails had been washed away during the spring rains, and long cliffside hikes simply weren’t our family’s thing yet.  That’s the beauty of travel — sometimes you learn what works for your family, and what doesn’t.

After two nights at the beautiful oceanside Hotel Pasquale, we found ourselves eager to return to Rome for one final walkabout.

Italy — and specifically Rome — had pulled us in hook, line, and sinker.