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

The all-inclusive beach resort vow renewal

Destination: Turks and Caicos

Number of travelers: 14

Trip organizer: Cathy Harney, age 66

We planned a weeklong Caribbean trip, not realizing it would coincide with our 40th wedding anniversary. With guests arriving from different cities, organizing everything felt overwhelming. My daughter, an experienced trip planner, finally said, “This is too much.”

Sheila Cannon of Carefree Romantic Vacations recommended a Beaches resort in Turks and Caicos and handled the details. My husband, Brian, gets anxious about travel, so I “kidnapped” him—our playful tradition. Once his compression socks were on, I revealed the destination, and we left the same day.

He knew our kids would be there but had no idea about the rest. At the resort, family and friends surprised him one by one. It was emotional and unforgettable.

Since we arrived late due to COVID, Sheila and my daughter planned a surprise vow renewal. A staff member handed me orchids and Brian a corsage. Turning around, we saw a decorated gazebo, our loved ones, and an ocean backdrop. It was a perfect way to celebrate 40 years together.

Big resort tips

Check child policies. Some resorts, like Sandals, are adults-only, while Beaches welcomes families.

Ask about group discounts. Some resorts offer a free room for every six or twelve booked.

Allow for downtime. With different interests, not everyone needs to stick together. We met for dinner but had flexible mornings.

Consider room preferences. Some prefer individual rooms, while others like suites. Choose accordingly.