Traveling Italy in the Off-Season with a Toddler: Lessons Learned

Exploring the streets of Rome

Traveling with a toddler is always an adventure, but doing it in the off-season adds a unique layer of challenges and rewards. Italy in November is quieter, cooler, and less crowded—a dream for avoiding tourist chaos but a bit trickier when it comes to transportation, restaurant options, and managing naps on the go.

Here are the biggest lessons we learned from two weeks of exploring Italy with our 2 year-old, and why I’d do it again (with a few tweaks).

1. The Off-Season Trade-Off

The Pros:

• Fewer Crowds: Popular spots like the Colosseum and Lake Como were delightfully empty. We rarely had to wait in line, and taking photos without a sea of strangers was a breeze.

• Lower Costs: Flights, Airbnbs, and even day-to-day expenses like food and transportation were significantly cheaper compared to peak season.

• Peaceful Vibes: Towns like Matera and Alberobello felt almost magical without the summer tourist bustle.

The Cons:

• Limited Options: Many restaurants and shops were closed, especially in smaller towns like Alberobello and Polignano a Mare.

• Weather Uncertainty: While we had plenty of sunny days, rain can derail plans (like our canceled ferry to Amalfi).

• Shorter Days: With sunset around 4:30–5:00 PM, we had to pack our activities into fewer daylight hours.

💡 Lesson Learned: Plan your itinerary around shorter days and have backup options for weather-dependent activities. Don’t count on everything being open, and embrace the quiet and adjust as needed.

2. Transportation in the Off-Season Can Be Tricky

Italy’s public transportation is reliable, but the off-season brings its quirks. Ferries don’t always run, train schedules can be sparse, and strikes (like the Trenitalia strike we encountered) are more common than you’d think.

We learned to:

• Book ferries early (or have a backup plan).

• Check train and bus schedules carefully; regional buses often have fewer departures in the off-season.

• Be flexible and ready to pivot; renting a car for our Puglia day trips was a lifesaver when tours and public transit didn’t work out.

💡 Lesson Learned: Renting a car can give you much-needed flexibility, especially for reaching off-the-beaten-path destinations like Matera or Alberobello. Just be prepared for narrow roads and ambitious Italian drivers.

3. Traveling with a Toddler: Survival Tips

Pack Light but Smart

Heres a link to my Toddler Travel Essentials for International Flights 

Backpacking with a toddler is no joke, but small essentials made all the difference:

• A baby cot that attaches to the plane seat (from Amazon) gave Asher a comfy space to sleep on long flights.

• Tray table covers and organizers keep toys and snacks contained during travel.

• Quiet, compact toys like his favorite trains or Montessori books worked wonders at restaurants and on the go.

Adjust Your Pace

Toddlers don’t care about itineraries, so we built in extra time for exploring parks, grabbing gelato, or just letting Asher run around in open spaces like the boardwalk in Salerno or the playground in Varenna.

💡 Lesson Learned: Slow travel is key. Pick fewer destinations and spend 2–3 days in each place to allow for downtime and toddler detours.

4. Accommodations Matter

Choosing Airbnbs over hotels gave us more space, access to laundry facilities, and a kitchen for preparing snacks and simple meals. However, location is everything:

• In Como and Bari, central locations meant easy access to sights but also some street noise at night.

• In Salerno and Sorrento, quieter locations made for more restful stays.

💡 Lesson Learned: Always read reviews for noise levels, especially if traveling with kids. Having a washing machine and extra bedrooms can make a huge difference for family travel.

5. Embrace the Unpredictable

One of the best parts of traveling with a toddler is that the unexpected often leads to the most memorable moments. From chasing pigeons at the Milan Cathedral to discovering a whimsical chocolate shop in Salerno, some of our favorite experiences weren’t on the itinerary.

💡 Lesson Learned: Build flexibility into your plans. Whether it’s allowing time for an extra playground stop or pivoting to a different town when transportation falls through, the ability to adapt makes for a much smoother trip.

Would I Do It Again?

Absolutely. Traveling in the off-season allowed us to experience Italy in a quieter, more intimate way. Yes, there were challenges… managing a toddler’s energy while navigating last-minute transportation changes isn’t for the faint of heart, but the memories we made were worth every logistical hurdle.

If you’re considering a trip to Italy with little ones, don’t shy away from the off-season. Just go in with realistic expectations, pack a little patience, and be ready to embrace the slower pace of life