Multigenerational trips almost always include a traveler who moves through the world differently, a grandfather in a wheelchair, an aunt who can't do stairs. The amateur itinerary either excludes them or revolves around them, and both get felt. The design brief I use instead: they should be part of everything, with a graceful exit available.
“You have to drag them along the journey.”
The design language
- Choose experiences where presence doesn't require participation, he's at the vineyard table with everyone, and can excuse himself when he's ready, no production required.
- Bring the entertainment to them: the chef comes to the villa, the musician plays the terrace, the family gathers where they already are.
- Handle requirements invisibly: main-level bedroom as a hard requirement, gate-level meet for him while everyone else gets curbside. He experiences ease, not accommodation.
- Ask the person, not just the family, often what he wants most is simply to be near everyone, not on every excursion. Design honors that instead of overriding it.
Claire's own numbers
The framework, step by step
- 1
Choose experiences where presence doesn't require
participation — he's at the vineyard table with everyone, and can excuse himself when he's ready, no production required
- 2
Bring the entertainment to them
the chef comes to the villa, the musician plays the terrace, the family gathers where they already are.
- 3
Handle requirements invisibly
main-level bedroom as a hard requirement, gate-level meet for him while everyone else gets curbside. He experiences ease, not accommodation.
- 4
Ask the person
not just the family — often what he wants most is simply to be near everyone, not on every excursion. Design honors that instead of overriding it.
Claire's own framework from this essay, in the order she teaches it.
Source: Claire B. Soares, from her own travel business and live trainings.
The villa-versus-hotel decision
This is also where the villa-or-hotel choice gets real: a villa gives the family one shared heart, but you're sourcing the chef, the housekeeping, the transport yourself. A hotel puts service on tap at the cost of that living-room togetherness. For families anchored by a less-mobile elder, I often split the difference: villa for the gathering, hotel-grade services contracted in. Dignity is a logistics problem, and logistics is what they hired you for.
Common Questions
How do you plan a multigenerational trip?
Design so the least-mobile traveler is part of everything with a graceful exit available: presence without required participation, entertainment brought to them, and requirements handled invisibly.
Villa or hotel for a family with an elderly traveler?
A villa gives the family one shared heart but you source the chef, housekeeping, and transport. A hotel puts service on tap at the cost of togetherness. Often the answer is a villa with contracted services.
What should you ask the traveler themselves?
What they actually want, which is frequently just to be near everyone rather than on every excursion. Good design honors that instead of overriding it.
Written By
Claire B. Soares
6× Condé Nast Top Travel Specialist, Certified AI Consultant, and founder of Travel AI University. $3.4B+ in enterprise travel software sold to Google, IBM, Boeing, the federal government, and the DoD; $16M+ in luxury travel sales with Up in the Air Life.
About Claire
