Milestone Travel Ideas: Celebrate Life’s Big Moments with Meaningful Trips

Hola Rosebuds!

Life has a funny way of rushing past us while we’re busy answering emails, showing up for everyone else, and trying to remember if we already washed that load of laundry (spoiler: we didn’t). But every now and then, something happens that makes us pause… A birthday, an anniversary, or even just the end of a really hard season. And in those moments, travel isn’t just a vacation. It’s a way to honor where you are, who you’ve become, and the road you took to get here.

I’m a big believer in celebrating life while we’re living it, not just marking it with a quick dinner out or another gift that ends up collecting dust. For me, celebration looks like boarding a plane, waking up somewhere new, and letting the rhythm of a different place remind me that I’m still alive and evolving.

Milestones Deserve More Than Dinner Reservations

Turning 40? That’s not just a number—it’s a rite of passage. An anniversary? That’s a story, a journey, a whole damn saga worth honoring. And yes, making it through a particularly soul-sucking work season without quitting everything and running off to Bali (unless that is your plan—in which case, call me) is also worth celebrating.

At my house, we’ve made it a bit of a tradition to mark the big birthdays with travel. For my 40th, we took a month-long sabbatical and wandered through Thailand, Bali, Kuala Lumpur, and Singapore. My husband’s 40th took us to the beauty of Portugal (which, honestly, feels like an underrated love letter waiting to be read). For my good friend’s 40th birthday, we island-hopped through Greece, soaking in that white-washed, blue-domed goodness and partying in Paradise (a beach club in Mykonos that felt like South Beach). 10 years later and I'm honored to be planning their 50th birthday adventure! And next up? Spain for our anniversary. Because nothing says “we still like each other” like tapas, flamenco and late-night strolls through Sevilla.

Choose Places That Match the Moment

Not every destination hits the same, and that’s the point. The energy of the trip should match the energy of the celebration. Here are a few of my personal go-tos for those memory-making moments:

Thailand + Bali

If you’re craving a blend of adventure, beauty, and the kind of deep exhale your nervous system has been begging for—this is it. One day you’re temple trekking at sunrise, the next you’re floating in a jungle infinity pool questioning why you don’t live here full time (ask me how I know).

Portugal

Food, wine, music, and culture all wrapped up in old-world charm. Whether you're wandering through Lisbon’s cobblestone alleys or sipping vinho verde in the Douro Valley, Portugal is a gentle, delicious kind of magic.

Greece

Greece doesn’t whisper. It sings. Loud, joyful, full-of-life energy that makes you want to dance in the street and toast to everything—yourself included. Sunsets in Santorini, fresh seafood in Naxos, and ruins in Athens if you need a little historical perspective.

Spain

This year’s pick for our anniversary. Spain has a way of pulling you in slowly—through siestas, sangria, and late-night laughter. Whether it’s the coast, the countryside, or the city, there’s something deeply satisfying about how Spain does celebration.

You Don’t Need a “Big” Reason

Let’s be real—sometimes the small wins are just as big. Maybe you survived a breakup, finally launched that business idea, or are coming out the other side of a funk that nobody even knew you were in (hello). That counts. That definitely counts.

You don’t need permission to press pause. You don’t have to wait for the perfect timing. Celebrate now. Create your own milestones if life’s being stingy with them. It's literally good for your health!!

A Few Things I’ve Learned Along the Way

Don’t wait for someone else to initiate it. Your joy isn’t a group project. Travel is self-care.

Lean into what you want, not what you think you should do.  This one is BIG. Maybe your dream trip isn’t five-star luxury. Maybe it’s an off-grid cabin where nobody talks to you for a week. Cool. Go.

Travel expands how you see yourself. Something about navigating a new place makes you realize how capable (and fun) you still are.

Final Thoughts? Celebrate Your Life—Loudly and Often.

Whether it’s a milestone birthday, an anniversary, or just a quiet urge in your spirit that says I need this, listen to it. Travel has a way of bringing us back to ourselves in the most beautiful, unexpected ways.

So book the trip. Toast the wins. Take the damn photo. And let the moment be enough.

Cheers🥂

~Dijna