With Noah’s 13th birthday coming up this summer, we gave him the chance to choose a destination for a special trip to celebrate. His pick was Italy, the birthplace of pizza and home to many historic sites he’s studied in the past few years of homeschool, and in December 2022, we purchased our flights from Chicago to Rome for a 9-day Italian adventure.

Our itinerary includes overnights in Venice, the Cinque Terre, Lucca, and Rome. About two-thirds of the stops are at least a little familiar to Amanda and me, as we spent 15 days in Italy in 2005 as part of a Cornell College music tour. The other third — including the Cinque Terre and a planned day trip to Naples — will be new. That said, we’ll lack the curated itinerary, motor coach, hired tour guides, and other benefits that came with the group experience. For this trip, we’ve cobbled together a half dozen train rides to connect our stops in Italy along with a mix of Airbnb and hotel stays.

Any international trip from the middle of Iowa is bookended with long travel days, and this trip is no exception. After spending Easter Sunday with family in Ottumwa, Amanda, Noah, and I left at 7:00 the next morning for our journey that includes:

  • 5 hours of driving to the Chicago Airport
  • 3 hours to eat, park, and check in
  • 9 hours flying to Rome
  • 3 hours to get through customs and from the Rome Airport to the train station
  • 4 hours on a high-speed train to Venice
  • 45 minutes on a vaporetto boat from the train station to St. Mark’s Square
  • 25 minutes on a shuttle boat to our hotel, the JW Marriott Venice Resort, which is on its own Venetian island

The first leg of our travel couldn’t have gone more smoothly, with stops for Amanda and Noah to get breakfast pizza at Casey’s in Sigourney and a gas, drink, and bathroom break at the forgettable Dekalb oasis along I-88. I identified a Jeni’s Ice Creams along our route to O’Hare Airport, so our first stop in the Chicago area was for lunch at a nearby restaurant followed by ice cream followed by a short drive to the airport parking.

I evidently wasn’t looking for the traditional leaving home photo.

Shake Shack and Portillo’s were considered (at least by me) for lunch, but a healthier, fresher restaurant won out as we decided to eat at True Food Kitchen. We were all impressed with our meals which included Noah’s Margherita pizza, Amanda’s Korean noodles, and my poke bowl. We were given wellness ‘shots’ while we were waiting for our meal and treated to a complimentary dessert of flourless chocolate cake and ice cream from our friendly waiter. True Food Kitchen was a little spendier than the aforementioned alternatives, but I’d happily dine there again when we’re in the Chicago area.

We’ll learn soon how True Food Kitchen’s version of Margherita pizza compares to Italy.

My poke bowl featured a unique black ‘forbidden’ rice.

Amanda decided not to double up on the ice cream, but Noah and I both finished out our lunch stop with a walk to Jeni’s — a Jeni’s we’d last visited in 2019 before we flew from Chicago to Lisbon and the Canary Islands. I had a scoop of their seasonal biscuits and peach jam and Noah had his new favorite ‘biscuits with the boss’ flavor, inspired by the Ted Lasso TV show.

A throwback to 2019, from our last stop at the Oak Brook Jeni’s Ice Creams.

Despite some ominous Google reviews of O’Hare’s economy parking situation, we had no problems finding a spot, boarding a shuttle to the transit center, and boarding a train to the terminal. We got our boarding passes, made it through security, bought some Garrett’s popcorn, FaceTimed with the girls, and before too long, we boarded our flight to Rome.

On the short train ride to the airport.


I try to stop at Garrett Popcorn during every trip to O’Hare Airport.

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