The multi-generational trip is the one we are asked to design most often and the one most likely to go wrong in the planning. Three generations means three speeds, three bedtimes and at least two ideas of what a holiday is for. Done well, it is also the trip people talk about for the rest of their lives. The difference is almost entirely in the structure.
Decide who the trip is for
Someone is usually paying, and someone is usually the reason. A seventieth birthday, a first grandchild, a last summer before university. Name it. It tells us whose comfort comes first when there is a trade-off, and there is always a trade-off: the lodge with the best guiding has stairs; the villa with the pool is forty minutes from the beach.
One base beats a tour
Touring suits couples. Groups of eight to fourteen do better with one or two bases and days that fan out from them. A private house in Laikipia, a villa above the Amalfi coast, a catered chalet in Courchevel: each lets the early risers go out while the rest have breakfast, and brings everyone back to the same table at night. Changing hotels every two days with a party that size costs a morning each time and tires the people least able to say so.
Build in the gaps
The most useful thing in a multi-generational itinerary is empty space. One activity in the morning, nothing fixed in the afternoon, dinner together. Children swim, grandparents read, parents disappear for an hour. We also plan at least one day in the week with nothing in it at all, and we place it in the middle, when the party needs it most.
Where it works best
Kenya for a first safari with children of mixed ages, because the private houses have pools, guides used to children and no minimum ages. South Africa for a party that wants a city, wine and bush in one trip with short internal flights. Italy and Greece for a villa week with easy days out and food that pleases everyone. The Alps in summer or winter for a group that wants to be active together without a long flight.
What to decide first
Dates, before anything else, because school terms and work diaries narrow them quickly and the best houses go a year ahead. Then the budget and who is contributing to it; we send one proposal with the figure broken down so the conversation is easy. Then the party, with ages and anything we should know about mobility, diet or fear of flying. Everything else is our job.
