Where the magic of Main Street meets the charm of cobblestone escapes.

From Disney enchantment to European elegance, your vacation should feel like a dream—before you even pack a bag.

Meet your travel BFF (who also happens to be a planning pro)

Hi, I'm Holly!

I’m a travel advisor with Once Upon a Time Vactions, a proud mom of three adventurous kiddos, and a wife to my favorite travel buddy. My love for exploring the world started long before motherhood, and over the years I’ve collected stories, memories, and meaningful connections in every corner of the globe.

Before I began travel planning, I spent 15 years teaching middle school theater—helping students step into confidence and creativity on stage. When I became a mom, my priorities shifted, and I found a new kind of fulfillment in helping families create unforgettable trips that feel easy, thoughtful, and full of joy.

These days, when I’m not mapping out itineraries, you’ll find me with my family—out exploring, curled up for movie night (popcorn included), or hosting holiday gatherings with all the sparkle and spirit. Christmas is my favorite time of year, hands down.

I’m especially drawn to places that feel layered and magical—Paris for its charm, and Walt Disney World for the memories it’s given my family again and again.

Whether it’s a family adventure, a romantic getaway, or something entirely custom, I’m here to help you plan a trip that feels as effortless as it does memorable.

my services

From Castles to Coastlines, Consider It Handled

All-inclusive planning for magical vacations

Disney & Theme Park Vacations

From classic character dining to Lightning Lane strategy, I plan magical, stress-free theme park trips tailored to your family’s pace and preferences.

Winter Ski Wonderlands

Thoughtfully planned ski vacations designed for ease, comfort, and connection—so your whole crew can enjoy the magic of the mountains, without the stress.

Beach Getaways

Think turquoise waters, breezy resorts, and perfectly timed excursions—all planned with your relaxation in mind.

Cruises & Group Trips

Whether it’s a multi-gen cruise or a girls' getaway, I coordinate every detail—so all you have to do is pack and show up.

European escapes

From Paris to Positano, I craft curated itineraries that balance iconic sights with hidden gems, luxury stays, and seamless travel days.

Booked, Packed, and Raved About

Here’s what happens when planning feels easy and fun.

Holly put so much time, care, and energy into every detail of our trip, and it truly showed. She made the entire experience feel seamless, special, and so memorable. We felt completely taken care of and can’t thank her enough!
The Walkers
Our family trip to Disney World was absolutely magical, thanks to Holly! Every detail was meticulously planned, making our experience stress-free. We couldn’t have asked for a more organized and delightful vacation!
The Smiths
Our getaway to Jamaica was nothing short of spectacular! Thanks to the expert planning and attention to detail from Holly, everything from where we stayed to the excursions were flawlessly arranged. We truly enjoyed a relaxing and unforgettable experience!
The Stephens
Our cruise vacation was a dream come true! The itinerary was perfectly organized, and every aspect of our trip was streamlined, allowing us to fully enjoy our time together. We can’t wait to book our next adventure!
The Bagleys