Most multigenerational trips to Italy start with a picture, not a plan. The whole family in one place, everyone together, often for the first time in years or the only time it will happen. What’s missing isn’t the idea. It’s someone who can take that picture and turn it into a trip that works for every generation in it.
And that’s usually where it stalls. You can picture the trip it’s meant to become, but not where to start, or how to make it work for all of them at once while holding the whole thing together. Not because anything has been missed. A trip across so many different ages can’t be assembled from places and activities. It has to start by understanding the family, every person in it, before a single day is planned.
THE TRIP THAT WORKS FOR ALL OF YOU hasn't BEEN BUILT YET.
Search for a multigenerational trip and the offer is always the same. Kid-friendly activities. A pace that suits the grandparents. It sounds right, but it starts in the wrong place, with the activities.
What actually makes a day work for a family like yours sits underneath the activities, in the needs that are easy to miss. The energy each person has, and when. How much rest the days need to allow for. What each one can eat, can manage, can walk. How much of the time the family spends together and how much apart, and the kind of space that allows for both. What tires the youngest and what tires the oldest, which are rarely the same thing. These are the things a trip has to be built on, and they have to come first, before a single activity is chosen and planned.
Start with the activities and fit the family into them, and you have skipped the part that decides whether the trip works. The places might be lovely, the pace reasonable, and still someone is left out, because it was shaped around what suits most families, not around what yours needs. Understand those needs first, and the rest, the places, the pace, the activities, follows from them. That is why the trip that works for all of you hasn’t been built yet. No one has started from your family.
I UNDERSTAND YOUR FAMILY before I PLAN THE TRIP.
The person who comes to me is usually the one in the family who took this on, and they feel the weight of it. Responsible, in their own mind, for making it the trip of a lifetime for every single person in it.
That pressure comes from carrying it alone, trying to guess what everyone needs and hoping it lands. It doesn’t have to be yours to hold.
So before I plan anything, I start by understanding the whole family, each person in it. Planning a multigenerational Italy trip begins with a questionnaire personalised for your family, not a place or an activity. Their needs, energy, and limits, what they want and what they would rather skip, captured directly instead of guessed. The trip gets built on what each person actually needs.
That way the responsibility for getting it right becomes mine, not yours. Everyone has a moment that is theirs, no one is left out, and you are free to enjoy it with your family.
Retirement is one of the few things that gets the whole family in one place at once. After a working life of making time for everyone else, the trip that marks it should not be one more thing to organise. I plan all of it, around the person retiring and everyone coming to celebrate them, so for once they are simply there with their family.
A big birthday is the family choosing to gather around one person. Not an ordinary trip to Italy, but a few days where they feel celebrated and everyone has the kind of time together that stays with them. I plan it all around the person whose birthday it is, so the celebration is theirs and none of the arranging is.
The first conversation is free. No packages, no pressure – just a real discussion about your trip and whether we’re the right fit for each other.
PLANNING YOUR TRIP
For most families, seven to ten days. That is long enough for a slow first day while everyone adjusts, and for the rest a wide range of ages needs, without the group tiring halfway through. The right length depends on who is travelling, which is one of the first things I work out. A trip with young children and grandparents in their eighties is paced differently from one with teenagers and active sixty-year-olds.
By understanding the family before planning anything. Before I suggest a place or an activity, I learn what each person needs: their energy, their limits, what they want and what they would rather skip. The trip is then built so every generation has moments of its own, with time together and time apart. Starting from the family rather than from a list of sights is what decides whether a trip across many ages actually works.
For a group with a wide range of ages, or anyone with limited mobility, one base usually works better, often a private villa that gives the group the space and shared living a hotel cannot. It takes the packing, the transfers and the repeated check-ins out of the trip and gives everyone somewhere to return to at their own pace. Some trips use two bases. Which is right depends on the group, so I decide it from what each person can manage, not from a fixed route.
Yes, with the right choices. The honest part is that some of Italy’s most famous places are the hardest. The Amalfi Coast, Cinque Terre and the hill towns are built on steps and steep lanes, while others are far easier, and the difference is in the planning. I do not build the trip around one person’s limits. I look for the version that fits everyone, in the logistics and in what each day does, so the group stays together.
Usually ten to fifteen, though there is no fixed maximum. I have planned for groups as large as thirty-five, so it is less about a number than about what actually works for the people in it. On ages, generally six and up, with exceptions. I do not add toddlers by default, because the pace that suits a two-year-old pulls against everyone else, but every family is different and I am happy to talk it through.
No. Every trip is built from scratch for the family it is for. Modular planning works from a fixed group of suppliers the planner places everyone into, the same villas, drivers and activities reused from one trip to the next. I source the ones that fit your family and what it needs instead, whether or not I have used them before. I can work this way because I am a fee-only planner. I take no commission from a villa, an accommodation or an activity, so nothing is in your trip because it pays me to put it there. The only reason anything is included is that it is right for your family.
I work on a fee-only basis. You pay a planning fee for designing and coordinating the trip, and you pay every supplier directly at their own price. The fee is also what keeps me on your side. My income is that fee, not a cut of what you book, so I have no reason to point you toward anyone I have a deal with. I am working for the family’s interest, not a supplier’s. The first conversation is free, and I explain the fee for your trip once I understand its size and shape.
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