How I Plan Travel by Season of Life (Not a Bucket List)
How I Plan Travel by Season of Life (Not a Bucket List)
For a long time, I thought travel planning was about collecting destinations.
Italy.
Safari.
Paris.
“One day.”
But over time — and after planning trips for hundreds of families — I realized something important:
Not all trips belong in the same season of life.
And when you try to plan them that way, travel starts to feel overwhelming instead of exciting.
So I stopped thinking about travel as a bucket list and started thinking about it as a timeline — one that changes as your life changes.
Travel Works Best When It Fits Your Life
Your energy changes.
Your responsibilities change.
Your family changes.
The trip that feels right in one season can feel exhausting, stressful, or mistimed in another. That doesn’t mean you’re doing travel “wrong.” It just means the timing matters.
When I plan travel — for my clients and for myself — I think in three buckets:
Partner Trips
Family Trips
My Trips (growth and work-related travel)
Each serves a different purpose. Each belongs in different moments.
Partner Trips: Travel That Reconnects You
Some trips are about the two of you — and only the two of you.
Partner trips aren’t about seeing everything. They’re about slowing down together.
These trips often show up:
After a busy or stressful season
To celebrate a milestone
When you need space away from logistics and decisions
They don’t have to be long. A weekend reset can be just as powerful as a two-week escape — if it fits your life right now.
This is also the season where splurging can make sense:
A better hotel
Easier transportation
Fewer plans, done well
Partner trips work best when they feel intentional, not rushed.
Family Trips: Why Timing Matters More Than the Destination
Family travel changes — because families change.
The trips that work when kids are little look very different from the trips that work with teens. That doesn’t mean one is better than the other. It just means they require different planning.
When I plan family trips, I think about:
Ages and interests
Energy levels
How long we really have
How many locations make sense
Some of the most meaningful family trips are tied to timing:
A last summer before high school
A graduation trip
A season where schedules finally align
There’s no “best age” to travel with kids. There’s just the right fit for your family right now.
The goal isn’t doing it all.
It’s choosing a trip that feels shared, manageable, and memorable.
My Trips: Travel for Growth (With Boundaries)
Some travel isn’t about rest — it’s about perspective.
As a travel advisor, I’m offered trips often. Suppliers want to show me what they’re building, and I want to experience destinations firsthand so I can serve my clients well.
But the “when” of my life right now is my family.
So my me trips are intentional — usually one or two a year — planned around our partner and family trips.
I don’t take them unless they:
Fit our family schedule
Deepen trusted supplier relationships
Help me better serve the destinations my clients ask about most
These trips aren’t perks. They’re an investment — in learning destinations deeply, understanding experiences firsthand, and helping clients get it right the first time.
Travel should support your life — not compete with it.
Travel as a Timeline, Not a Checklist
The biggest shift I’ve made is this:
Stop asking, “Where do we want to go?”
Start asking, “What kind of trip fits this season of our life?”
There’s no one-size-fits-all answer.
Just the right trip for right now.
And when travel fits your life, it stops feeling like something you have to “figure out” — and starts feeling like something you actually enjoy.