Italy Wasn't Perfect. That Was Kind of the Point.
Listen to Episode 44
Kim's Family Went to Italy on Points — Post-Trip Report
Kim came back to tell me what actually happened after all the planning: Rome, Pompeii, Capri, a positioning-flight disaster, a memorable boat day, and plenty of lessons learned.
Quick Takeaways
- An international positioning flight is one place Kim wouldn't gamble on timing again.
- Sometimes spending a little more is worth more than maximizing every dollar.
- Booking direct can unlock experiences at a fraction of third-party tour prices if you're willing to do the research.
- Points and miles can make the trip possible, but they can't make travel predictable.
- Some of the stories a family remembers most are the ones nobody planned.
The Trip Almost Fell Apart Before It Started
Kim's family of six needed to position from Indianapolis to JFK before their flight to Rome. There was a 7 a.m. option and a noon option. They chose noon.
The 7 a.m. flight left. Their noon flight — along with the later options — was delayed and eventually canceled. Suddenly the goal wasn't maximizing points. It was getting six people to Italy.
They found American Airlines availability from Indianapolis through Chicago to Rome for 30,000 miles per person. Kim and Chris each booked three tickets, and the canceled positioning flight resulted in about $1,300 back. Air France also ultimately refunded the miles from the original JFK–Rome awards without charging the cancellation fee.
“We know that when you have an international travel flight, you should get there significantly early, maybe even the day before.”
— KimWhat Kim Would Do Differently
Give an important international award flight much more breathing room. Kim knew the conventional advice before this trip; this was the trip that made her stop gambling on it.
The “Free” Rome Hotel That Surprised Everyone
The hotel had already caused plenty of stress before the trip because of a delayed opening. Once the family finally arrived, though, it became one of Kim's favorite surprises.
They had three rooms and weren't relying on meaningful Hyatt status there, but Kim couldn't say enough about the service. When they left for the airport at 1 a.m., the hotel had six breakfast boxes waiting — including a vegetarian one specifically for her son — without Kim even asking.
Rome: The Colosseum Tickets Were Worth the Work
The original flight disruption cost the family their first set of Colosseum underground tickets. Chris went back to work and managed to secure another set directly for their last day in Rome.
The family's direct tickets cost about $80 total, dramatically less than the third-party tour prices Kim had been seeing. More importantly, the underground experience ended up being one of the highlights.
“That underground tour was so worth it.”
— KimOne of the Best Rome Days Was on Two Wheels
The family also spent a day riding e-bikes through ancient ruins outside central Rome before visiting the catacombs. It was active, memorable, and something Kim said she'd absolutely recommend.
Their travel setup was smart too: portable fans for the heat, crossbody bags, and tiny collapsible cups they could use at Rome's drinking fountains.
Sometimes Maximizing Value Means Spending $10
After one particularly packed public-transit experience in Rome, Kim had reached her limit. So when she learned there was an air-conditioned train to Pompeii with assigned seats for about $10 more per ticket than the crowded option they had considered, the decision became very easy.
They explored Pompeii without a formal tour. Chris loves history, so he ended up explaining what they were seeing as the family moved through the site. Kim still thought Pompeii was absolutely worth the trip.
And Then There Was the Boat Day...
This was supposed to be one of the splurges of the trip: a private boat day around Capri. At first, it was even better than Kim expected. The boat that arrived was an upgraded, more luxurious version of what she'd thought she booked. Music was playing. The kids were lounging and dancing. The weather was beautiful.
Then they started idling near the Blue Grotto.
One by one, almost everyone started getting seasick. Robbie threw up over the side. They tried swimming to land for relief, only to discover the rocks were incredibly sharp — and Chris ended up with bleeding feet.
Eventually they made it to a restaurant, exhausted, after a very expensive boat day that had gone nothing like Kim pictured.
“It's not about it being perfect.”
— KimAnd that's where the story changes. Kim realized that this disaster wasn't ruining the trip. It was becoming part of it.
“This is probably the one story that they retell over and over again.”
— Kim
Good to Know: Their EES Experience
Kim's family waited about 90 minutes entering Rome. On the trip home, their Paris connection included another EES checkpoint. They hurried straight there and still waited roughly 45 minutes. With about a two-hour connection to start, they reached the gate with only around 20 minutes before boarding.
That's one family's experience, not a universal connection-time rule — but it changed how Kim thinks about connecting through Europe with children.
Air France Business Class — and Another Lesson Learned
Kim and one daughter flew home in Air France business class while Chris and the other kids were in economy. Her daughter loved it, and Kim was very happy to have the business-class seat on the way home.
But after experiencing the split herself, Kim said she probably wouldn't divide the family that way again. It's another example of something that can look great on paper but feel different once you actually try it.
The Part of the Trip That Stuck With Kim
At the end of our conversation, Kim wasn't talking about the value of her hotel rooms or whether she'd maximized every point. She was talking about perfectionism.
“I have lost some of my perfectionism with traveling with this trip because I realized even without being perfect, you create a perfect trip.”
— KimThe positioning flight went wrong. They lost a day. The boat day turned into a seasickness adventure. They didn't see everything they'd planned to see.
And Kim came home wanting to travel more.