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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 middle

The 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 this

Have 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 three

Do 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 problem

All 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 makes teenagers tolerable on group trips.

Do not rent a villa

This is the most counterintuitive piece of advice I have, and it’s going to stop people mid-listen. The villa seems perfect. It seems cost-effective. It seems like everyone has space and the setting is beautiful, and you’ll have long lunches on a terrace. You’re dreaming about drinking a glass of wine by the pool, napping in a hammock, gazing at the rolling hills of Tuscany. You’re not thinking about who gets stuck doing all the driving, how many rental cars you’ll actually need, sharing a bathroom with people you don’t normally share bathrooms with, who is going to make breakfast every morning, who is going to go grocery shopping for the coffee and breakfast foods, who is going to be picking up towels, or who thinks the A/C isn’t strong enough and wants to call the owner — but oh wait, you call, you have the number, and you took Spanish in high school, right? Yeah, Spanish is not just like Italian. You know why hotels cost more? Because they head off a million little annoyances.

What it actually means is that the person in the middle is now doing the driving, grocery shopping, morning coffee, meal planning, and activity coordination — on top of everything they were already doing. The villa removes all the infrastructure that actually gives the middle generation a moment to breathe.

The alternative: a large apartment in a city. Florence, or even the outskirts of Florence, where you can walk or take a short train into the center. Here’s what that buys the middle generation — the ability to walk out the door, find a piazza, sit in a café, have a glass of wine, and exist alone for forty-five minutes. That is not a luxury. That is the thing that makes the difference between coming home restored and coming home more depleted than when you left. No matter how loving and well-intentioned everyone in the group is, the middle generation will need that exit. Build it into the trip’s structure before you go.

On the ground: how to structure each day

The toughest part about traveling with an older generation is that people aren’t always honest about their limits — and sometimes they’re not honest with themselves. Or they get confronted with those limitations for the first time on the trip. Walking around a suburban neighborhood every day is very different from traversing cobblestone streets in humid Rome.

This is why I recommend booking one activity everyone does together each day, and then leaving time for people to do things on their own. A private tour solves a lot of problems. You’ll have a guide to lead the way, a local person to ask questions of, skip-the-line tickets already taken care of, and a shared experience that everyone will inevitably process differently — and talking about it later becomes an experience unto itself. Then leave the second half of the day open. Take in more history, shop, park yourself in a piazza and gelato the afternoon away.

For dinner, reservations are a must in the most popular destinations — there’s a lot of very mediocre, if not downright bad, food in the most touristy places. For a big group you’ll need to plan ahead. You can make reservations directly through the restaurant’s website or through thefork.it. One meal together per day — a lunch or a dinner — and then leave people to do their own thing.

When to call a professional

If you want everything planned — drivers, restaurant reservations, guided tours across multiple cities — I strongly urge you to book through a professional. The value you’ll receive, especially when amortized across all the people and problems in the group that are easily mitigated, is tremendous. We just had a family return from a multigenerational trip to Sicily: roots day, city and countryside stays, daily guided tours, van rides between cities, and restaurant reservations for lunch and dinner every day. For a pro, this is easy. For the DIY traveler, plan to take a sabbatical from work to get it done.

So if you’re DIY-ing it: keep it simple. One tour a day, one meal a day, and basta.

The reframe

A multigenerational trip to Italy is one of the most meaningful things a family can do. It is also very complicated in ways that nobody who hasn’t done it will warn you about. Going in with clear eyes about the dynamics, the logistics, and the invisible labor does not diminish the experience — it protects it. The families who have a terrible time are almost always the ones who planned the fantasy and ignored the logistics. The ones who have a transformative time are the ones who planned both.

If you’re in the middle of planning a multigenerational trip to Italy and want someone to pressure-test it before you go, that’s exactly what a one-hour consultation is for. I’ve seen what works and what doesn’t. If you’re a committed DIY-er, I also offer Customized Itinerary Design, where I go much deeper than best advice and actually plan the day-by-day — but you make the bookings. And if you want to turn it over to Arianna and me to just handle it, make an appointment for a free Bespoke Trip Planning consultation, where I’ll be able to give you a price estimate once I know more about your ideal trip.

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