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Multi-Generational Travel: How to Plan a Trip Everyone Actually Enjoys

Three generations, one villa, and a plan that gives everyone a day that feels like theirs.

By Jeralin Soares · July 29, 2026 · 8 min read

Plan around energy, not age

Grandparents who hike will out-pace teenagers who do not. Sort the group by energy and appetite for activity rather than by generation, then build days that let those groups split and reconvene.

One shared meal a day is enough

The most successful family trips anchor on a single daily gathering — usually dinner — and leave the rest of the day open. Mandatory togetherness from breakfast to bedtime is where good intentions go to die.

Settle money before departure

Who pays for what, how shared costs are split, and what happens with tips and excursions should be agreed in writing before anyone travels. It is an uncomfortable conversation once and a very uncomfortable one daily.

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