Our 14-Day Italy Itinerary: Traveling with a Toddler in the Off-Season
This wasn’t our first trip to Italy, which made planning this one a little more specific. We’ve explored the classics—Rome, Florence, Sienna, Pisa, Milan, Cinque Terre, Venice—and this time, we wanted to focus on places we hadn’t been before while also revisiting a few highlights, like Rome, for my mom, who was traveling with us for the first time.
It’s worth noting that this isn’t necessarily the itinerary I’d recommend for a first-timer in Italy. This trip was very tailored to us: a mix of seeing new things, exploring with a toddler, and avoiding long-haul flights like last year’s 14-hour trek to Japan. We aimed for variety: lakeside towns, unique countryside stops, family-friendly cities, and, of course, a touch of ancient history.
Here’s how we spent two whirlwind weeks in Italy—what worked, what didn’t, and why we’d do it all over again.
Days 1–3: Lake Como
We started with a flight from Atlanta to Milan and had originally planned to take a train to Como City. But when we arrived at the Milan airport, we realized the next train wasn’t leaving for another two hours. With a toddler in tow, waiting around didn’t seem like the best idea. After chatting with a taxi driver, we discovered that the fare to Como was the same as going into Milan, so we decided to skip the train entirely and head straight to the lake.
Highlights in Lake Como
Stayed in Como City for easy access to transportation (key when traveling with a toddler).
Explored Bellagio and Varenna by ferry, where Asher enjoyed a lakeside playground while we soaked in the views.
Took the tram up a mountain for panoramic views of the lake, definitely a highlight.
💡 Tip In the off-season, ferries run less frequently, so plan ahead to avoid getting stranded.
Days 4–6: Puglia (Bari, Matera, Alberobello, Polignano a Mare)
Next, we flew from Milan to Bari, our base for exploring the unique charm of Puglia. Bari itself is more of a practical hub than a destination, but it gave us easy access to Matera, Alberobello, and the stunning seaside town of Polignano a Mare.
Highlights in Puglia
Matera: Imagine an entire city built into ancient caves. Walking around Matera felt like stepping into a different world—or maybe a movie set.
Alberobello: The trulli (cone-shaped houses) were whimsical and unlike anything else we’d seen in Italy.
Polignano a Mare: A gorgeous coastal town perched on cliffs above the Adriatic. We visited at sunset and were blown away by the views, even though much of the town was quieter in the off-season. If you go in warmer months, the grottoes and beaches would be incredible to explore.
💡 Tip: Renting a car for this leg of the trip gave us the flexibility to visit all these spots at our own pace. Just be mindful of train schedules or be prepared to hire a taxi if delays strike, like they did for us.
Days 7–9: Salerno and the Amalfi Coast
We chose Salerno as our base for exploring the Amalfi Coast because it offered the perfect balance of practicality and charm. Staying in Amalfi itself would have been expensive, especially in the off-season when there isn’t much happening in the small town. We also considered stopping in Naples to break up the trip, but opted for a direct route to Salerno since it’s just as convenient for visiting Pompeii.
Highlights in Salerno
Enjoyed the wide boardwalk and the festive atmosphere as Christmas lights were being put up.
Took a slightly chaotic bus ride to Amalfi for a day trip, an adventure in itself!
Loved the relaxed vibe and accessibility of Salerno, which made it a great hub for this part of the trip.
Days 10–11: Sorrento
If you only go to one place on the Amalfi Coast, make it Sorrento. Ok maybe thats just my opinion but It’s family-friendly, has stunning views, and strikes the perfect balance between lively and peaceful. It may not be that perfect “picture” from the internet you want, but thats why you have Google and in my opinion the views are even better.
Highlights in Sorrento
Took family photos near the Cloisters of San Francesco and down by the beach.
Spent a day just wandering the streets, stopping for gelato, and admiring the Christmas tree in the square.
Stayed in an Airbnb walking distance with a washing machine, which is a great fit for families.
💡 Tip: Sorrento wins over Amalfi for accessibility, charm, and fewer tourists. It’s also a great base for day trips.
Day 12: Pompeii
My mom hadn’t been to Pompeii and we wanted her to experience the ruins. Let me just say: strollers and cobblestones do not mix. It was a lot of carrying Asher and juggling gear, but seeing Pompeii on a beautiful sunny day with clear views of the volcano made it worth it.
Days 13–14: Rome
Rome was the perfect place to end our trip. It was my mom’s first time, so we revisited the big sights, and staying near the Colosseum made everything feel extra special.
Highlights in Rome
Took family photos with a local photographer, so much better than awkward selfies
Explored the Colosseum and Forum. Pro tip: Bring ID to match your ticket because they WILL check
The Trevi Fountain was drained for maintenance, but they let visitors walk above the basin, which was a cool experience.
Why We Chose This Itinerary
This trip was about mixing new and familiar experiences. We skipped places like Venice and Florence because we’ve been before, and instead focused on spots like Matera and Alberobello that felt truly unique. That said, every traveler is different, and this itinerary worked for us because it combined slower days with ambitious sightseeing… and let’s be honest, plenty of gelato breaks.
Summary
Day 1: Travel (Atlanta to Milan)
Days 2–4Lake Como
Days 5–6: Bari, Matera, Alberobello, Polignano a Mare
Days 7–9: Salerno, Amalfi
Days 10–11:Sorrento
Day 12: Pompeii
Days 13–14: Rome
Final Thoughts
Traveling in the off-season with a toddler wasn’t without its challenges, but it was absolutely worth it. From the quiet charm of Sorrento to the surreal beauty of Matera, this trip gave us the perfect mix of adventure and family time. If you’re planning your own Italian adventure, I hope this inspires you to explore beyond the big cities and embrace the unexpected.
Would we do it again? Absolutely. (Though next time, maybe we’d think twice about our stop over in Naples.)
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