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Jessica Holloway

Welcome to Holloway on Main
Where Your Dream Vacation Begins!

Ready to turn your travel dreams into magical memories? The World Awaits—Let Holloway on Main Take You There. At Holloway on Main, planning your perfect getaway is not only fun—it’s FREE! As your personal Holloway on Main Planner, I bring years of travel experience, insider knowledge, and a true passion for making vacations unforgettable.

Why Choose Holloway on Main?

Whether you’re dreaming of castle magic at Disney, sailing the high seas on a cruise, or relaxing on a sandy beach, I’m here to help every step of the way. From park tickets and hotel reservations to dining plans, and PhotoPass tips, I’ll take care of the details so you can focus on the fun!

Thinking Cruise?

Let’s explore the perfect destination together—complete with exciting offshore excursions and fun-filled activities for all ages aboard the ship. Now I’d love to help create magic for your family.

Why Trust Me?

My first trip to Disney World was in 2006 with my now-husband’s family. I still remember how much time and effort my mother-in-law put into planning that trip—she spent months making sure I would see every character and ride every ride. I was amazed by the love and detail she poured into every moment. That experience made me fall in love with Disney, and I have her to thank for it.

From that moment on, I knew Disney would be part of Loren and my future. We honeymooned at Disney World, dreaming of the trips that would follow. Since then, we’ve found every excuse to go back officiating a friend’s wedding, our oldest son’s first trip, and more. When we adopted our second son, we celebrated by taking him to our “second home.” And when we were matched with our daughter, we used the magic of Disney World to announce our growing family.

Disney has been woven into so many of our life’s biggest milestones. And just like Ruth did for me on that first trip, I plan each visit with the same love, care, and attention to detail whether it’s for my own family or for others. I want everyone I work with to experience Disney the way I did: full of joy, ease, and wonder.

Whether it’s your first visit or your tenth, my goal is to make it feel effortless like stepping into your second home