Travel that feels like the two of you.
Concierge planning for honeymoons, anniversaries, and Disney escapes.
Travel that feels like the two of you.
Concierge planning for honeymoons, anniversaries, and Disney escapes.
Concierge planning for honeymoons, anniversaries, and Disney escapes.
Concierge planning for honeymoons, anniversaries, and Disney escapes.
I'm Hillary Cummings : a Nashville native, wife, mom, and former teacher who has been planning intentional, deeply personal travel since 2023. In that time, I've helped travelers experience getaways that are custom-made with a concierge touch and none of the stress. My heart is in romance travel: honeymoons, destination weddings, anniversaries, the kind of Disney trips built for the two of you. (And yes — I still plan magical family vacations, too)

We talk through your vision, your preferences, and what you do and don't want... so your itinerary is yours alone.

From lodging to logistics, I handle it all from start to finish, with thoughtful, personal touches woven throughout.

Everything is handled. No Stress. No worries, and you know you have a partner that is there for you each step of the way.
Sheila B.

I design Walt Disney World honeymoons and adults-only Disney getaways that are romantic, unhurried, and entirely about the two of you

From the proposal-worthy resort to the moment you say "I do," I plan the celebrations that mark your love beautifully...without the overwhelm.

Sun-warmed sand, oceanside dinners, and a beachfront room with your name on it. The reset you've been craving is calling.

The islands are calling: waterfalls and volcanoes by day, golden-hour quiet by night. A trip that feels like paradise awaits.

Bucket-list cities and slow, romantic itineraries — Paris balconies, Italian coastlines, the trip you've always promised yourselves.

Nothing quite beats the experience of sailing on open water, and if a vacation away from it all on a traveling luxury hotel is more your speed, let me help!

Magical family vacations will always have a home here. Traveling with kids of any age? I'll build park days that feel smooth, joyful, and genuinely manageable — minus the overwhelm.

No matter where you want to go, we begin the journey with my learning about your inspiration, you dreams, and your vision for a perfect vacation experience.
Tell me all about your dream vacation, the places you've always hoped to visit, your particular travel preferences, and your wish list as well as who you're traveling with and I'll take it from there.
My love language: Acts of Service. My favorite past-time: researching and learning all about the destinations that make my client's dreams come true. With a commitment to top-notch service and truly bespoke planning services, you can rest assured that I'll take care of every detail to bring your vacation dreams to life.
Find Your Wonder with Hillary
Copyright © 2003- 2026 Hillary Cummings, Find Your Wonder with Hillary
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