Plan Multi-generational Family Vacations Without the Stress-These six families show us how it’s done.

A four-generation Disney blowout

Destination: Disney World, Orlando, Florida

Number of travelers: 9

Trip organizer: Debbi Breeling, age 62

We spent years saving for this trip, and my husband and I covered the costs for everyone—my mother, two of our three children, their spouses, and our two grandchildren.

Walt Disney World is complex, with various ticket options and reservation requirements. It’s not a place where you can just show up and explore. To make planning easier, we hired a travel agent, Lauren Cardinale, who guided us through the process.

All of us downloaded the Disney World app, and Lauren linked our accounts so one person could manage reservations for the entire group. The app also included a GPS map, making it easy to navigate the park.

Our trip lasted eight days. My grandchildren were enchanted by experiences like lunch at Beast’s Castle, but for me, the real joy was watching them spend time with my mother. It’s true—theme parks create lasting memories for both kids and adults.

Amusement park tips

Work with an authorized Disney planner. These experts have insider knowledge on crowd levels, schedule changes, and park logistics.

Stay off-site for larger groups. On-property accommodations for groups of 10 or more are limited and book up quickly—reserve at least a year ahead.

Schedule rest days. Breeling built in free days between park visits to allow the family time to recharge.