Every outdoor family eventually plans the big one: the trip where three generations fly somewhere warm together, grandparents included, for a milestone birthday or an anniversary. It is a wonderful idea and a genuinely different planning problem from a weekend under canvas. The instincts that serve you on a campsite still apply — plan around the group, not the individual — but the scale is another matter.
The first decision, and the one that quietly determines all the others, is where everyone sleeps. Booking six or seven hotel rooms scatters the group across corridors, triples the cost of breakfast, and means the toddlers and the early-rising grandparents never actually cross paths with the teenagers. For a group travelling together, a single large private house almost always works out cheaper per head and infinitely better for the shared meals and lazy mornings that are the whole point.
On a recent trip to Bali we ended up in a six-bedroom villa in Seminyak with its own pool and a cook who handled breakfast, and it reframed how I think about group travel entirely. The children had space to be feral, the grandparents had a quiet wing and a shaded terrace, and every evening the whole party ended up around one long table without anyone having booked a restaurant. The house did the work a good campsite does — it gave everyone their own corner and one place to gather.
Once accommodation is settled, build the itinerary around energy levels rather than a checklist. Mixed-age groups move at the pace of the youngest and the oldest, so plan one anchor activity a day and leave the rest loose. A pool, a garden and a kitchen absorb the in-between hours far better than a packed schedule ever will.
Handle the money up front. Agree who is paying for what before anyone books flights, split the house cost per couple or per room, and keep a shared running total so nobody is quietly resentful by day three. The trip is a gift you are giving each other; a spreadsheet at the start protects the goodwill at the end.