Ep. #601 | What Travelling to Italy for 15 days with Our Kids Taught us About Money

By Jenn Pike | July 16, 2026

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This week, I pulled my husband in to do a full recap of our family trip to Italy at the end of May. We were there for 15 days with our two kids (17 and 19 at the time), and honestly, a month later I’d hop on a plane back in a heartbeat.

We cover everything: how we planned it, how we paid for it, what we’d do differently, and the real, unfiltered truth about what it’s like to travel as a family of four for two weeks straight.

In this episode, we talk about:

  • How we used credit card points to cover four flights and how we scored a last-minute premium cabin upgrade for all of us for about $3,000
  • The difference between staying in hotels vs. Airbnbs, and why Airbnbs won for us every time
  • Why we’d skip the Amalfi next time (controversial, I know) and where we wish we’d spent more days
  • The hidden charges at Italian restaurants that caught us off guard 
  • How we average 20,000–30,000 steps a day and why getting lost on foot is genuinely one of the best travel strategies
  • Why we booked the Colosseum and Vatican three months out
  • Our honest take on Naples 
  • What it means to raise kids who know how to travel 

Let’s dive in!

Thank you for joining us today. If you could rate, review & subscribe, it would mean the world to me! While you’re at it, take a screenshot and tag me @jennpike to share on Instagram – I’ll re-share that baby out to the community & once a month I’ll be doing a draw from those re-shares and send the winner something special!

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Have a question? Send it over to hello@jennpike.com and I’ll do my best to share helpful insights, thoughts and advice.

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