Italy by car: hill towns, famous icons and a slow drive through Monaco

Travelling from southern France into Italy by car adds an extra layer to the journey. The route hugs the coast at times, passing places like Cannes and Nice, before cutting through the mountains and disappearing into a series of tunnels that suddenly deliver you into a completely different world.

We hadn’t planned to stop in Monaco, but when you’re already this close, curiosity tends to win.

A very slow drive through Monaco

Emerging from the tunnels into Monaco was instantly overwhelming. Traffic ground to a halt, streets narrowed, and what followed was less a scenic drive and more a very slow introduction to one of the most famous city-states in the world.

We had set our navigation to the city centre, specifically to a stretch of road that is normally part of the Formula 1 circuit. Progress was limited, but eventually we did manage to drive a small section of the actual circuit, curbstones and all, including the iconic tunnel, just at a far more modest speed.

Roadworks made parts of the waterfront harder to see, and the sheer density of traffic meant this was never going to be a relaxed stop. As a drive-through experience, though, it was oddly memorable. Monaco feels intense, compact and impressive, but also like a place best explored on foot, or saved for a different kind of trip.
 

A Tuscan base with a view: San Quirico in Collina

After a long travel day, we arrived in San Quirico in Collina, a small hilltop village surrounded by rolling Tuscan countryside. Our apartment sat high on the hill, offering sweeping views over vineyards, fields and distant villages. The scenery alone made the journey feel worthwhile.

The apartment itself was modern and more spacious than expected. While we made it work, we quickly realised it wasn’t the most practical choice with young children. The balconies were beautiful but low, doors easy to open, and there was no private garden. Something we really missed in Italy, where outdoor space makes such a difference for kids. Next time, we would definitely choose a place with a garden where children can safely play outside.

That said, it worked as a base. From here, several classic Tuscan towns were within easy driving distance, allowing us to explore without constantly changing accommodation.
 

Volterra: history, views and excellent gelato

Volterra was our first real introduction to Tuscany. The drive alone was worth it, winding through soft hills and patchwork fields before climbing toward the town’s ancient walls.

Volterra feels unmistakably Italian. Narrow streets, old stone buildings, city gates and layers of history everywhere you look. In a relatively compact walk, you pass a cathedral, one of Tuscany’s oldest town halls, archaeological remains and the ruins of a Roman theatre. There’s even a small park and playground, which made it surprisingly manageable with children.

We wandered at an easy pace and, inevitably, ended with gelato. According to Google, one of the best in town, and judging by the flavours and very happy faces, it lived up to its reputation.

Certaldo Alto: an unexpected highlight

Certaldo Alto turned out to be one of our favourite stops in Tuscany. The medieval village sits high above the modern town of Certaldo and is reached via a short but memorable cable car ride.

At the top, the atmosphere changes instantly. Brick streets, historic buildings and wide views across the Tuscan landscape. Certaldo is known as the birthplace of Giovanni Boccaccio, but beyond its literary history, it feels refreshingly calm. Parking was easy, crowds were limited, and the lack of English translations somehow added to the charm.

A brief rain shower sent us looking for shelter, conveniently coinciding with snack time. After that, we explored the entire historic centre in about an hour and a half, taking our time to enjoy the preserved architecture and views.

If you’re looking for a Tuscan hill town that still feels relaxed and authentic, Certaldo Alto is an easy recommendation.

Florence: iconic, impressive and very busy

Florence hardly needs an introduction. We began our visit in the Boboli Gardens, entering directly from a nearby parking area. This turned out to be one of the best decisions of the day.

The gardens offered space, greenery and room for the children to run freely while we explored statues, viewpoints and winding paths uphill. The kids loved it, far more than we had expected, and it felt calm and relaxed compared to the city streets below.

The Palazzo Pitti dominates the upper end of the gardens, vast and imposing, with what was once an amphitheatre stretching out in front of it. Even without entering the palace itself, the scale is impressive.

Once we left the gardens and entered the historic centre, the atmosphere shifted quickly. Streets narrowed, crowds thickened and moving through the city became intense. Crossing the Ponte Vecchio was memorable, but stressful with young children, and the same was true for much of the centre.

The Duomo remains breathtaking, no matter how many photos you’ve seen. The detail is astonishing. With long queues in the heat, we chose to admire it from the outside.

Florence is undeniably beautiful, but it’s also overwhelming. For families who prefer a slower pace and more breathing room, it might be better saved for a trip without young children, or for when they are a bit older.

Pisa and a last look at the Italian coast

Pisa wasn’t necessarily on our must-see list, but for the kids, the Leaning Tower was non-negotiable. It’s one of those landmarks they already knew, and seeing it in real life mattered to them.

The tower is exactly what you expect. Iconic, crowded and surrounded by people taking playful photos. It’s not a place you need hours for, but it’s fun to see once. After one last gelato in Tuscany, we continued towards the coast.

The beach offered a different side of Italy. Windy, lively and perfect for running, playing and watching the waves crash in. Swimming wasn’t an option that day, but it was a fitting way to end our time in Tuscany.

 

Looking ahead

Our time in Italy was filled with contrasts: famous cities and quiet hill towns, busy streets and calm countryside. Some places surprised us, others confirmed what we already suspected about travelling through iconic destinations with young children.

It was also here that our plans for the journey ahead began to shift. That story belongs in the next chapter.
   

Highlights

• Our highlight: Certaldo Alto & The Boboli Gardens
• The kids’ highlight: the Leaning Tower of Pisa

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