Three generations, one villa

Something has shifted in how families holiday together. What used to be an occasional gathering, engineered around a milestone birthday or an anniversary, has become for many families closer to an annual habit: three generations under one roof, grandparents funding or co-funding the trip as much for their own sake as anyone else's, because they have realised that the window in which grandchildren still want to come away with them is shorter than it feels.

Why it is growing

Part of it is straightforward economics of time. Parents are stretched, grandparents are often more available and more willing to spend on shared experience than on things, and a single well-chosen trip solves the perennial problem of family time being scattered across too many smaller, less satisfying visits. Part of it is also a quiet correction: after a period in which everyone travelled in their own narrow age bracket, honeymoons for two, girls' trips, school-holiday family runs, there is a renewed appetite for the kind of holiday where a grandfather can watch his grandchildren learn to swim, rather than hearing about it afterwards.

Space is the real question

The single biggest determinant of whether a multigenerational trip succeeds or quietly exhausts everyone is not the destination. It is whether the accommodation actually gives each generation somewhere to retreat to. A single very large villa can look impressive in photographs and still fail in practice if every bedroom opens onto the same living space, because a five-year-old's early mornings, a teenager's late nights and a grandparent's need for quiet will collide within about two days.

What works better is either a villa built in genuinely separate wings, ideally with a ground-floor bedroom and bathroom for anyone who would rather not manage stairs, or a small cluster of adjoining villas that share a pool and a dining terrace but not a roof. A private plunge pool or a shallow paddling area away from the main pool matters more than it sounds for a family with a toddler, since it removes the low hum of anxiety that otherwise sits under every adult conversation.

Together, and apart

The trips that are remembered fondly tend to share a structure rather than a location: one or two fixed communal anchors a day, most often a long lunch or dinner where everyone is expected, and long stretches either side left deliberately unplanned. Teenagers need the option to disappear with a paddleboard or a moped and a sibling for an afternoon. Grandparents need permission to skip an outing without it becoming a conversation. Toddlers need naps to happen on their own schedule, not the group's. A holiday that tries to keep everyone together for every meal and every excursion is, paradoxically, the one most likely to fray by day four.

Destinations that flex across ages

Some places simply do this better than others, usually because they combine a calm base with genuine variety close by. The Greek islands work well when kept to one cluster rather than an ambitious island-hopping itinerary: Paros and Antiparos, linked by a short ferry, pair calm swimmable beaches and walkable villages with just enough to explore, while Crete offers a fuller resort infrastructure and sits a short daily ferry from Santorini for a family who wants both.

Tuscany remains a genuine classic for a reason: a hilltop villa with its own pool can sit twenty minutes from both a real town and decent countryside, giving grandparents a quiet terrace, parents a change of scene, and children space to run that a hotel corridor never offers.

Mauritius suits families with younger children particularly well, since several stretches of its coastline, on the east coast at Belle Mare and in the north-west around Trou aux Biches among them, stay shallow and calm for long stretches, sheltered by reef, which takes the edge off the usual vigilance a beach holiday demands.

Family safari camps deserve one honest caveat: age policies vary a great deal and are worth checking property by property rather than assumed. East African camps in Kenya and Tanzania are often more flexible, sometimes welcoming young children on private game drives, while camps in South Africa and Botswana frequently set a minimum age of six, eight or higher for shared drives, with walking safaris and ballooning usually reserved for children of twelve and over. None of this rules safari out as a multigenerational option; it simply means the fit needs checking before it is assumed.