Behind the Scenes: Planning a Multigenerational Trip That Works for Everyone

Behind the Scenes: Planning a Multigenerational Trip That Works for Everyone

A rooftop aperitivo. A table full of pasta. Three generations laughing together. That is what made it into the photos from our Sicily trip. What they do not show is the wheelchair service I booked through the airport, the walker waiting for us at the hotel or the quiet planning behind the scenes that let my 90-year-old grandmother experience Sicily fully, without exhausting herself in the process.

Multigenerational travel is not about limiting what anyone can do. It is about getting creative so everyone gets to participate, in their own way.

Here is some of what went into making it work.

A little help through the airport

I booked wheelchair assistance for the airports, saving my grandmother's energy for the trip itself rather than the walk through the terminals.

A walker, waiting

A quick WhatsApp text to my partner, and a walker was waiting for us at the hotel, ready to help her navigate Sicily's cobblestone streets and uneven piazzas.

Drivers who know the way in

Many of Sicily's most beautiful old towns restrict private vehicles entirely. A private driver who knows the back roads and has the right access makes it possible to reach places a standard car never could.

Seeing Palermo without the steps

In Palermo, we traded a walking tour for a Fiat tour, so she could take in the city without the steps.

Room to enjoy it, differently

Some afternoons, I explored a little further on foot while she settled into a rooftop bar or a café in the piazza. Giving each of us room to enjoy the destination, just differently, was the whole point.

Every family has its own rhythm and its own needs, from the youngest members to the most seasoned ones, and building a trip around them is one of my favorite parts of this work. If you are dreaming of a multigenerational trip that includes every generation of your family comfortably, I would love to help you plan it.