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

The classic giant beach house confab

Destination: Corolla, North Carolina

Number of travelers: 18 to 20

Trip organizer: Charles Oransky, age 72

We've been visiting the Outer Banks (OBX) since the mid-1980s. It started with just my wife, our four children, and me. Now, each of our children is married, and we have eight grandchildren. Occasionally, a friend or two joins us as well.

We always rent a beachfront house, usually through Twiddy & Company. As our family has expanded, so have our housing needs. The last house we stayed in had two of everything—refrigerators, freezers, stoves—and even a second kitchen on another floor. We made full use of them all.

A house offers advantages over a hotel, especially with young children who need space to run and play. Of course, there are challenges—everyone has their own schedule and vacation style, and little kids can be noisy. But there’s always a way to find your own space. You can relax on the beach or by the pool.

Some of my favorite moments happen at different times of the day. I wake up early and take some of the younger grandchildren to the beach around 6:30 or 7 a.m. to watch the sunrise. Then, we pick up fresh bagels. Dinner is another highlight—everyone gathers at the table. It takes effort to organize, but it’s an incredible experience for us all. Many of our friends no longer vacation with their grown children, but for us, this trip is a tradition we cherish. We talk about it all year long. The best part is the countless small, unexpected moments that make it truly special.

Beach house tips

Book a year in advance. “We secure the house for the next year before we leave,” Oransky says. Demand is that high.

Stay longer if possible. “With a large group, it takes a few days to settle into a routine,” Oransky notes.

Plan meals wisely. Make one major grocery run at the start, bring essentials from home, rotate cooking and cleanup duties, keep dinner as the main group meal, and skip restaurants, Oransky suggests.