Three generations, sometimes four. Children, parents, grandparents, occasionally an in-law or two. Different energies. Different mobility. Different ideas of what a holiday is for.
The mistake on multi-generational trips is to plan for the lowest common denominator. The grandfather can't hike, so nobody hikes. The toddler needs a nap, so the afternoon goes quiet. By the end of the trip, three people are content and seven are politely restless.
The work is in designing for parallel use. A villa with the right number of rooms, the right distance between them, the right shared kitchen. A safari camp that does both walking and game drives, so the energetic and the not-energetic can split. A cruise route with shore excursions tiered by intensity. The trip that works lets each generation have its own version of the holiday without the logistics requiring a second job from one of the parents.
A villa in Tuscany for ten, with the right cook and the right local fixer, beats a hotel almost every time for this kind of trip. The Caribbean reunion done at a private island. A south Indian month split across three properties, with the older generation flying home a week early.
I have done enough of these to know the conversations to have at the design stage, rather than at the trip stage, when it is too late.
The other five
When you're ready