Celebrate the Milestone, Take the Trip

Birthdays have a funny way of making you reflect.

Maybe it’s because I’m celebrating another trip around the sun this week, but I’ve been thinking about the way we mark the important moments in our lives.

There’s usually a dinner. A cake. Cards. Maybe a gift or two.

And I love all of those things.

But you know what I remember most when I look back over the years?

The experiences.

The places I’ve been. The people I’ve shared them with. The meals that lasted for hours. The things we laughed about. The adventures that didn’t go exactly as planned. And those moments when you stop, look around, and think, I can’t believe I’m actually here.

That’s one of the reasons I love the idea of celebration travel.

Celebrations Have Always Been Part of My Travel Career

In some ways, celebration travel has been part of my career from the very beginning.

I started out planning destination weddings, helping couples take one of the biggest days of their lives and turn it into an experience they could share with the people they loved.

From there came the honeymoons—and perhaps surprisingly, New Zealand has become one of my top honeymoon destinations. Not every newlywed couple dreams about spending a week lying on a beach. Some want beautiful scenery, adventure, incredible food and wine, and experiences they’ll remember forever.

Over the years, the celebrations have expanded far beyond weddings and honeymoons.

I’ve planned trips for milestone birthdays, big anniversaries, family reunions, girls’ getaways, and multigenerational vacations where the entire family comes together to celebrate.

I’ve even been lucky enough to occasionally become part of the celebration myself.

While I was in Australia at the same time as clients celebrating a 60th birthday, I had the pleasure of taking them out and celebrating with them. I’ve also been part of a group of couples who gathered in St. Martin for a big birthday celebration.

Those are some pretty special memories from this career of mine.

One Milestone, One Very Special Trip

One of the things I love about celebration travel is that the destination can reflect the particular moment in your life.

I’ve had clients who have shown that beautifully.

One couple celebrated a 50th birthday in Hawaii.

Their honeymoon took them to Tahiti.

And when it was time to bring the family together for a family reunion, they chose the Maldives.

Three very different occasions. Three very different trips.

That’s exactly the point.

No single place is perfect for every celebration.

The right destination is the one that fits you, the people you’re traveling with, and what you’re celebrating.

Bring the Whole Family

Some of my favorite celebration trips have been the multigenerational ones.

A big anniversary is a wonderful reason to bring everyone together—not just the couple who reached the milestone, but their children and grandchildren too.

And these trips become about so much more than the anniversary itself.

Grandparents get uninterrupted time with grandchildren. Adult children get to reconnect. Everyone steps away from work, school, sports, appointments, and the million other things that make getting the entire family together increasingly difficult.

Instead of receiving another gift, the couple celebrating that big anniversary gets something much harder to wrap:

time with the people they love.

And everyone comes home sharing the same collection of memories.

Sometimes the Experience Is the Celebration

You don’t necessarily need balloons waiting in the room or a cake delivered after dinner to make a trip feel celebratory.

Sometimes the experience itself becomes the moment.

Watching the sun set somewhere you’ve always dreamed about visiting.

Sharing an incredible meal.

Seeing Australian wildlife you’ve dreamed about encountering.

Sipping wine among the vineyards.

Waking up over a turquoise lagoon.

Seeing a favorite sporting event in another country.

Getting the whole family together when everyone’s schedules finally align.

Or simply raising a glass somewhere beautiful and realizing how fortunate you are to be there together.

Those are the things we tend to talk about years later.

And unlike another sweater or gadget, you don’t eventually clean them out of a closet.

Tell Me What You’re Celebrating

This is something I always want my clients to tell me.

If you’re traveling for a birthday, anniversary, honeymoon, retirement, reunion, graduation, or another special occasion, don’t treat it like an insignificant detail.

Tell me.

It helps me understand what this particular trip means to you.

Maybe we should build an experience into the itinerary. Maybe one resort is a better fit for the occasion than another. We may find special options we wouldn’t otherwise consider.

And sometimes it’s the little touches that turn an already wonderful vacation into something you’ll remember forever.

That’s part of the fun of planning celebration travel.

Don’t Wait for the “Big Enough” Milestone

I think we sometimes convince ourselves an occasion has to be significant enough to justify a trip.

The 50th birthday.

The 25th anniversary.

Retirement.

But who decided the years in between don’t count?

You don’t necessarily need a zero at the end of the number to have something worth celebrating.

Life gives us plenty of reasons to put things off. There will always be another bill, another commitment, another project at work, or another reason that next year might be more convenient.

I’ve learned enough through my own travels—and through the lives of the people I’ve planned trips for—to know that we aren’t guaranteed the perfect time.

If the people you love can travel and there’s somewhere you’ve been dreaming about experiencing together, that’s worth considering now.

Another Trip Around the Sun

This birthday week has been filled with friends and family, laughter, dinners, surprises, and people I love.

And that’s really what celebrating is about for me.

It’s not so much about adding another candle to the cake.

It’s about recognizing that another year has given me more people, places, and experiences to be grateful for—and hopefully plenty more adventures still ahead.

So when your next milestone rolls around, you can certainly make the dinner reservation.

Buy the cake.

Open the presents.

But maybe you should also pack the suitcase.

Because sometimes the best way to celebrate another chapter of life is to go somewhere and live it.