Recently, a friend confessed to me that she struggled with the idea of traveling to the same place over and over, because there is so much of the world to see. As someone who’d like to see as much of our planet as I can before I die, I nodded my head in agreement. Her point is valid. Yet, there’s something that happens when you return to your favorite spot(s) time and time again - they start to feel “yours”, and become a meaningful part of the fabric of your life story. That is how I feel about Italy. I’ve been a handful of times, but every time I go, I want to return as soon as possible. I actively miss it when I am home. Maybe it’s because a huge percentage of my heritage hails from Italy (primarily Sicily, but also Tuscany/Florence), but it could also be that, as millions of people can attest, the country is just a magical place. It never gets old for me (well, maybe the growing crowds do), and I am eternally grateful to have the opportunity to travel there with my kids and have it become a part of their childhood, too.

Italy is a very regional country, with different foods, customs and landscapes wherever you go. Prior to this trip, I hadn’t spent any time in Northern Italy, so we planned an itinerary that would give us a sampling of this area of the country. Our trip kicked off in Milan, and then we traveled East to Verona, and then, to Venice. From there, we returned to familiar territory, driving South to Tuscany and then, finally, to Rome. Our trip was 2 weeks in total, with our longest stay being in Venice.

When we travel to Italy with kids, we have a more relaxed approach to planning our days. We usually pick 1 “touristy” thing to do each day (a museum, historical location or pre-planned activity), but spend the rest of our time just wandering around, popping into the shops and food establishments that catch our eye, and really trying to get a sense of place for wherever we are staying.

This is the longest, most detailed travel recap that I’ve published here - it’s my hope that it can be a helpful planning tool for anyone who is traveling to Italy! You can also reference my 2023 trip recap to Rome, Florence and Tuscany here, or get my tips on planning a fantastic vacation here.

For my paid subscribers - don’t miss the very end of this post where I need your feedback on an exciting future project (Italy related!). I would love to hear your thoughts, and you’ll be first to know if/when this does come to fruition.

A few things to note: