One Trip, Many Ages: How I Plan Family Vacations That Everyone Actually Enjoys
If you’ve ever tried to plan a vacation with kids of multiple ages, you already know the math doesn’t add up easily.
One child needs naps.
One wants nonstop activity.
One insists they’re “too old” for family trips, until it’s time to actually miss one (my second oldest is college bound soon).
And somehow, you’re expected to make it magical for everyone.
I know this firsthand. My own children are 18,19, and 6. We travel often together. And now, I’m planning a trip that includes all of us plus my grandson, who will be just six months old.
That’s four generations, wildly different needs, and very different definitions of “fun.”
What Real Life Family Travel Has Taught Me
Traveling with kids at different life stages has taught me one big lesson: the destination matters more than the itinerary.
When my older kids were little, vacations revolved around naps and early nights. As they grew, their interests changed: more independence, more thrill rides, more freedom. Now, with a baby joining the mix, flexibility is non negotiable.
The goal was never to make everyone do the same thing at the same time. The goal was to choose places where everyone could have their version of a great vacation (without stress).
Why Destination Choice Is Everything
I can plan a beautiful schedule, but if the destination doesn’t support mixed ages, it becomes exhausting fast.
That’s why my go to recommendations (and my own family’s go to choices) are destinations that are built for variety.
Disney Cruises (My Personal Favorite)
If you ask me what works best for families like mine, my answer is easy: a Disney cruise.
In fact, that’s exactly what I’m planning for my family now.
Here’s why it works so well:
Dedicated nurseries and kids clubs by age
Teen spaces that feel cool—not forced
Adult-only dining, lounges, and quiet areas
Shows and entertainment that everyone enjoys
No constant packing, planning, or logistics
My older kids can do their own thing without feeling stuck in “kid mode.” My 6-year-old gets the magic Disney is known for. The baby can stay on a familiar schedule. And the adults? We actually get to relax.
That balance is everything.
Disney Destinations Beyond Cruises
Disney parks and resorts work for similar reasons:
Attractions for every age and comfort level
Rider Switch for parents with younger children
Elevated dining and experiences for adults
Disney is one of the few brands that truly understands multi age travel.
All-Inclusive Resorts
For families who want simplicity, all-inclusive resorts are another strong option.
I recommend them often because:
Kids clubs are separated by age
Teens get independence in a safe environment
Parents don’t have to think about every meal or activity
They remove decision fatigue—and parents feel that immediately.
How I Structure Days to Avoid Burnout
I don’t believe in packed schedules, especially with kids.
My approach is simple:
One main activity per day
Built-in downtime
Optional plans, especially for older kids
This allows babies to nap, younger kids to reset, and teens to feel respected, not dragged along.
Parents Deserve to Enjoy the Vacation Too
This is the part I’m passionate about.
Parents are allowed to:
Use kids clubs without guilt
Book adult-only dinners or spa time
Sit quietly with a coffee or cocktail while someone else handles entertainment
When parents are relaxed, the entire family feels it.
Traveling with kids of different ages (including babies and young adults) isn’t about lowering expectations. It’s about choosing destinations that support real families with real needs.
If my family can do it, with teenagers, a young child, and a baby, you can too!
And when it’s planned right, family travel doesn’t just work, it becomes something everyone looks forward to.
