34 Days in Italy With a Toddler

*After learning our lesson. More on that below.

We just got back from 34 days in Italy with our toddler, Tristan. It got cut short. But here's everything we learned about doing long-term international travel as a family—the logistics, the gear, the mistakes, and the stuff nobody tells you.

I'll be honest: my wife Michelle is the trip architect. She plans the routes, finds the stays, and keeps the itinerary loose enough to actually work with a toddler. But there's a real system behind it.

Google Flights Price Monitoring

Set up price alerts for your target dates. Don't commit to exact dates until you see a dip. We watch for 2-3 weeks before booking. The difference between a Tuesday departure and a Saturday can be hundreds of dollars per person.

Don't Overplan Transportation

We book trains and buses a couple of days before, not months. Prices in Italy don't spike the way they do for flights. This gives you flexibility to stay an extra day if a place is great, or leave early if it's not.

Airbnb Strategy

Cheaper than hotels, especially for 34 days. But risky—you're gambling on photos being accurate, the neighborhood being walkable, and the host being responsive. We had great ones and rough ones. Budget flexibility is the key: if an Airbnb turns out bad, you need to be able to pivot to a hotel for a night without it breaking the trip.

The Timezone Hack (If You Work Remotely)

If you're someone who works remotely on US East Coast hours, this is the thing that makes extended travel viable:

Mornings are completely free for sightseeing and family time. Travel on weekday mornings when trains are empty—tourists and locals both clear out. Weekends, stay put and explore the city you're in.

Every item on this list earned its spot over 34 days. Nothing we brought "just in case."

Connectivity: eSIM for Data

We used Holafly for mobile data in Italy. It worked, but speeds were disappointing—noticeably slow for video calls and uploads. If I did it again, I'd try Saily instead, which has better reviews for European coverage. The GL.iNet router paired with a good eSIM means all your devices get data through one plan.

After the transatlantic flight, we should have spent at least one night in Venice. Instead, we connected straight to Palermo. Landed late. Exhausted. And then the car seat situation happened.

We'd booked a van transfer and specifically requested a car seat. But there was a miscommunication—the original driver who had the car seat got sick. They sent a replacement driver who showed up without one and was visibly annoyed about the whole situation. The coordinator was shocked and apologetic, but at midnight with a tired toddler, you just want to get to the hotel.

We crashed at a hotel near the train station. Rough first night. Everyone was running on fumes.

After the rough arrival, Palermo settled into a rhythm. Seven days was enough to stop feeling like tourists and start feeling like we lived there. Palermo has a rawness to it that's completely different from the polished tourist zones up north.

We got around on local buses and trains. With a toddler, the pace is slower by default—which actually works in Sicily. Nobody's in a rush.

Western Sicily is a different world from Palermo. Quieter, more coastal, fewer tourists. Trapani and Marsala are small enough to walk everywhere—which is exactly what you want with a stroller.

Here's something nobody tells you: the Palermo-to-Naples ferry is a cargo ship that also takes passengers.

It was delayed. Then at each island stop, the crew had to unload freight—pallets, vehicles, supplies. You're sitting there with your toddler watching forklifts operate at 2am. It's an experience.

Was it rough? Yes. Is it the cheapest way from Sicily to the mainland? Also yes. And honestly, Tristan was mesmerized by the cargo operations. So maybe it's a feature, not a bug.

The Amalfi Coast is stunning and completely unoptimized for strollers. Stairs everywhere. Narrow streets. Buses that wind along cliff roads. With a toddler, you learn to slow down—or you lose your mind.

The upside: when you're not fighting the terrain, it's one of the most beautiful places on earth. And the slower pace means you actually sit down and eat instead of rushing to the next viewpoint.

Ischia is what Capri wants to be but without the crowds. A volcanic island with hot springs, quiet beaches, and actual Italian families on vacation instead of just tourists.

Four days was perfect. Enough to unwind after the Amalfi intensity. The ferry from Naples is short and easy—nothing like the Palermo cargo ship experience.

Matera is where Italy stops performing for tourists. The ancient cave dwellings (Sassi di Matera) are a UNESCO site and genuinely unlike anything else in the country. Less English, less infrastructure, better food, lower prices.

Bari was a transit stop more than a destination—one night before catching the train to Rome. But the old town (Bari Vecchia) is worth a walk through if you have a few hours. The trains are slower and less frequent in the south, but the weekday-morning strategy worked perfectly here.

By Rome, we had 34 days of Italy under our belts and a toddler who was completely adjusted to the rhythm. Rome with a stroller is doable—the centro storico has more flat ground than the Amalfi Coast, and Romans are surprisingly patient with kids.

Rome is also where we had a hospital visit with Tristan. He's fine now, but in hindsight, if we'd had a portable O2 monitor from the beginning of the trip, we might have caught it earlier. The EU healthcare system was thorough but the wait times were long. The silver lining: the bill was shockingly cheap compared to what it would have cost in the US. Something to be said for countries with real healthcare infrastructure.

We flew home from Fiumicino. After 34 days of ground transport, the airport felt almost foreign.

1. Take a rest day after the transatlantic flight. The Venice-to-Palermo same-day connection was the worst decision of the trip.
2. Book the ferry cabin. Seat-only on a cargo ferry with a toddler at midnight is unnecessary suffering.
3. Bring fewer clothes, do more laundry. We overpacked for 34 days. Every Airbnb had a washing machine.

But would I do 34 days in Italy with a toddler again? Without hesitation. The timezone hack makes remote work viable. The trains make ground transport easy. And Tristan will grow up knowing that the world is bigger than our neighborhood.

That's worth every cargo ferry at 2am.

Gear List (Full Links)

Everything we brought, with links. These are affiliate links—they help support this site at no extra cost to you.

• UPPAbaby Minu V2 Stroller
• Stroller Travel Bag — has AirTag slot, ours is tearing but still works
• Stroller Organizer Bag — hooks on handle, replaced our diaper backpack
• Aer Travel Pack 4 (35L) — solid, front pocket could open wider
• GL.iNet Travel Router — newer models have eSIM support
• Sony A6000 Body
• Sony 16-50mm Kit Lens — budget option, no OSS
• Sony 18-105mm f/4 Lens — recommended upgrade, has OSS + more range
• RideSafe Portable Car Seat — brought as backup, barely used