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

The family dream cruise

Destination: Alaska

Number of travelers: 22

Trip organizer: Jenny Gillett, age 45

My grandma always dreamed of taking the entire family on a cruise, but my grandpa never agreed. After they both passed, my dad decided, “It’s time to make Grandma’s wish come true.” So, we set sail.

Our group of 22 included my parents, six siblings, their spouses (except one who couldn’t make it), and all our children. The trip was postponed twice due to COVID, and each time we rebooked, we opted for an upgrade. By the time we finally boarded, we had secured eight connected balcony rooms, allowing the kids to move freely between them.

For anyone planning a cruise, the first step is consulting with a cruise line expert—they save a tremendous amount of effort. My biggest challenge was ensuring everyone had the necessary travel documents. The highlight for most of us was seeing the Hubbard Glacier up close.

After two years of separation due to COVID, some family relationships had become strained. That week on the cruise, simply spending time together helped us reconnect. I believe Grandma would have been happy to see us all enjoying each other’s company again.

Family cruise tips

Appoint one negotiator. “I handled all the questions with the cruise consultant,” Gillett says, streamlining communication.

Designate a representative for each family unit. This prevents confusion and keeps planning simple.

Check medical services in advance. The onboard medical staff played a crucial role during a heart-related emergency.

Consider a smaller ship. Some Alaska cruises accommodate 4,000 passengers, but the Gilletts chose one half that size for a more comfortable experience.