Ep. 38: How to Plan Multigenerational Travel to Italy

Are you thinking about a trip to Italy and need help getting started or refining your plan? Book a one-hour consultation, my specialty, and let me help you ensure it’s the best trip possible.Among my favorite trips to plan are multigenerational family trips — especially when they involve a roots-finding day for those with Italian ancestry. But really, the reason I enjoy planning these so much is that I know how much value I can offer. There are so many things you don’t know that you don’t know, because planning one of these trips is genuinely not easy.Everyone is excited. Everyone has a different film running in their head. The boomers want Dolce Vita — the café, the piazza, the slow lunch. The Gen X/Millenial parent dreams of wandering like Before Sunrise, unscheduled and open. The grandkids want Pisa for TikTok. Everyone thinks their version of Italy is the best one. The gap between the fantasy and the logistics nobody discussed is what this episode is about.The weight lands in the middleThe first thing I want to name is something nobody says out loud. When grandparents offer to pay for a significant portion of the trip, it feels like a gift — and it is —, but it also creates an invisible obligation. Now, the Gen X or millennial in the middle is responsible for making sure the investment pays off. Grandma needs to be comfortable. The kids need to be engaged. The teenager needs wifi. The eighty-year-old needs to sit down every twenty minutes. And somewhere in there, the person holding all of this together needs to have something that resembles a vacation.This is not a complaint about multigenerational travel. It’s an honest description of the dynamics so that the middle generation can go in with their eyes open and build a trip that accounts for what’s actually going to happen — not just what everyone imagines will happen.Before you book anything, do thisHave the bucket list conversation — but do it properly. Not “what do you want to see?” which produces a list of everything, or more commonly, a big uuuuuh, I dunno. Limit the options by raising the stakes: if you get to choose only one thing on this trip — the Colosseum or the Vatican — which one? Give people time to actually think. Let them sit with it for a few days. What comes back will surprise you. The grandparent who you assumed wanted the Vatican might actually want to see the Forum because her father talked about Rome his whole life, and that’s what he described. The teenager who you assumed wanted Instagram content might actually be obsessed with gladiators. You don’t know until you ask the right question.The purpose of this exercise is not to eliminate destinations. It’s to identify the two or three experiences that each person would be devastated to miss — and protect those ruthlessly — while letting everything else be negotiable.Keep it simple: two locations, not threeDo not pack in many locations. Seriously, two locations instead of three for a ten-day trip is plenty. I understand that you want to maximize the experience — you’ve spent all this money to fly across the ocean — but I’m thinking about how many times you need to get to and from a train station, all the bathroom trips the grandparents and the little ones are going to need while you’re trying to figure out what track your train is on, and getting taxis on either side that usually only fit four people. Your time is better spent people-watching in a piazza, trust me.If you’re choosing between Florence, Venice, and Rome, eliminate Venice. The narrow streets and difficulty getting a quick taxi when you need one can make the trip heavier than necessary.The Pisa problemAll the Gen Zs will say they want to go to Pisa. It’s purely for TikTok. And here’s the honest truth: Pisa is an entire day trip that won’t deliver much beyond the photo. You’re not eliminating TikTok moments from the trip — you’re not a monster — but you are being strategic about which ones are worth a full day and which ones can be woven into something you’re already doing. The leaning tower is a destination. A beautiful doorway in Florence or a terrazzo floor in Naples is a TikTok moment that happens on the way to something else. Let the kids find those. They will find them. Ludovica in Naples is the perfect example — she was finding restaurants with lines around the block that nobody had heard of, not because she was Italian but because she’s 16 and online.Give them one meal to find entirely on their own. Let them navigate one afternoon. Two things will happen: they’ll find something surprising, and they’ll feel like participants rather than passengers, which is what