
Hi, I’m Hillary—the founder of Find Your Wonder with Hillary, a travel advisor, storyteller, and lover of beautiful destinations, deep conversations, and that moment when your plane lifts off the ground and your real life hits pause.

I believe the best trips were never really about the places. They're about who you become while you're there, and who you're fortunate enough to have beside you. That conviction is the thread running through every itinerary I design, and it took root long before I ever called myself a travel advisor.
My journey began in wedding and event planning, where I had a front-row seat to one of life's most joyful kinds of chaos. I watched couple after couple pour themselves into the wedding—the flowers, the seating charts, the thousand small decisions—only to reach the honeymoon already depleted, planning the most romantic trip of their lives in the scraps of an overflowing season. It always struck me as backward. Your first adventure as a married couple should feel like an exhale, not one more line on the list. So crafting seamless, deeply personal honeymoon itineraries became one of my signature specialties, and it remains some of the work I love most.
But my expertise reaches well beyond honeymoons. Whether you're dreaming of a sun-soaked beach where the days blur together in the best way, the easy luxury of an all-inclusive resort, a cultural deep-dive through Europe, the particular enchantment of Disney, or an epic adventure on the high seas, I create tailor-made experiences built entirely around you. Romantic retreats, multigenerational family vacations, milestone celebrations worth marking properly, the islands of Hawaii and the Caribbean, a first cruise or a fortieth—each one planned with the same care, and none of them off the shelf.
I came to this work by way of the classroom and the page. I spent years as a teacher and have always been a devoted student of literature, and that training never quite left me. I still think in terms of story—of pacing, of meaning, of the small details that make a moment land. I bring that same lens to travel, because I'm convinced a trip is more than an itinerary. I think a great deal about the why beneath it: the emotional resonance of a place, the way the right experience at the right moment becomes something you carry home and keep, long after the tan has faded. That's the difference between a vacation that was lovely and a trip that changed something. The second kind is what I'm after, every time.
What that means for you is refreshingly simple: I take the guesswork out. I curate personalized itineraries shaped around who you actually are, handpick accommodations I'd be proud to send you to, and secure the kinds of exclusive experiences that turn a good trip into the one you'll still be talking about years from now. The research, the logistics, the late-night comparison of three nearly identical resorts—that part is mine to carry. Yours is the easy part: pack your bags and go.
Whether it's your honeymoon, a long-awaited bucket-list adventure, or a well-deserved escape you've put off for far too long, I would be honored to plan it with you. Let's turn your travel dreams into something real—and let's find your wonder, one incredible trip at a time.

The people who find me are almost never bad planners. They're the opposite. They've read everything, saved thirty tabs, polled two group chats, and ended up at eleven at night in a Reddit thread about whether they booked the wrong resort — somehow further from a decision than when they started.
That isn't a research problem, and more research won't fix it. It's what happens when something matters enough that you're afraid to get it wrong.
I've already done the looking, and I've done it in ways you can't from a laptop: in person, and through people on the ground who will tell me the truth about a property well before that truth shows up in a review. So I'm not handing you options to sort through. I'm bringing you the two or three that are genuinely right for you, and I can tell you exactly why.
Then I do the part no amount of research produces, which is give the trip a shape. Where the big day goes, and what has to sit on either side of it. When to schedule nothing at all. Which dinner is worth building an afternoon around, and which one you should skip so you can stay in the water another hour. That's the difference between a trip that's full and a trip that's good, and it's what people are describing when they tell me years later that they still talk about it.
I'm also not new at this. I've been the top-selling advisor at my agency more than once, I'm a member of CLIA and ASTA, and I work directly with partners including Sandals and a roster of boutique resort brands — which translates into resort credits, upgrades, and the sort of intervention that only happens when someone at the property knows your advisor by name.
And when something goes wrong at eleven at night in a time zone six hours ahead — a canceled flight, a closed restaurant, a sick kid — you text one person, and she's already fixing it.
Wherever you want to go—across the ocean, down the coast, or into the heart of your next big adventure—I’ll help you get there with less stress, more joy, and the kind of personalized support that makes travel feel easy (even if you’re traveling with toddlers or wedding guests or the entire family tree).
Your dream trip starts here—and I can’t wait to plan it with you.
Find Your Wonder with Hillary
Copyright © 2023- 2026 Hillary Cummings, Find Your Wonder with Hillary
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