Arielle Lewin

A Hotel Room in Miami Changed Everything

I was sitting in a hotel room in Miami, about to board a cruise I had planned for four families. Three of the kids had birthdays that week, and none of them knew their friends were joining the trip until breakfast that morning. Watching those kids lose their minds with excitement, I started scrolling Facebook and saw a recruiting ad from Favorite Grampy Travels. I sent a message before we even boarded the ship. A few weeks later, I had my interview. That was 2023, and I haven’t slowed down since.

Since then, I’ve planned over 300 vacations for families and groups. Walt Disney World, Disneyland, Disney Cruise Line, ocean cruises, Hawaii. If your family is trying to figure out how to make it all work without the stress, that’s exactly what I do.

What 300 Trips Have Taught Me

I’ve been to Walt Disney World and Disneyland more than 20 times. I’ve sailed on 22 cruises across 8 different cruise lines. I’ve completed the College of Disney Knowledge, earned my Disney Cruise Line Specialist and Adventures by Disney Specialist certifications, and I’m a certified Universal Orlando Resort Specialist and MSC Cruises Specialist, among others. The certifications matter, but the real education comes from being in the parks and on the ships over and over again.

Here’s what all of that has taught me: the difference between a good Disney trip and a great one usually comes down to a handful of decisions most families don’t even know they’re making. Such as, which park day to start with, when to book dining, and whether Lightning Lane actually makes sense for your group, or if your money is better spent somewhere else. These are the things that save you time, save you from costly mistakes, and turn a trip that could have been overwhelming into one where you actually get to relax and enjoy it.

I had a group of 25 family and friends sailing a European itinerary on Disney Cruise Line last year. Everyone had different needs for port days. About a month before sailing, the entire itinerary shifted when a port was removed, and another was added, bumping everything by a day. I had all of the excursions and hotels rebooked within a few days. Nobody in the group had to lift a finger. That’s the kind of thing that’s nearly impossible to sort out on your own, especially while juggling your regular life. My clients tell me they can give me an idea of what they want, and I make it a reality. That’s the part of this job I love the most.

A Teacher’s Approach to Your Family’s Trip

I’ve been a gifted and talented elementary teacher since 2002, and I’m still in the classroom. That background shows up in how I plan trips more than you’d expect.

I know what kids actually care about at different ages. I know how long a six-year-old can handle a park day before everyone hits a wall. I know that a well-timed character breakfast at Plaza Inn in Disneyland can turn a cranky morning into a highlight of the whole trip. And two decades of managing classrooms, lesson plans, field trips, and parent communication have made me very good at organizing complicated schedules with a lot of moving parts.

I’m also a Girl Scout leader, a band mom, and an adoption advocate. There is rarely a day without something on my calendar, and that is not an exaggeration. All of those commitments keep me sharp at multitasking and moving fast. When you send me your wish list, I don’t sit on it. I get to work.

Tips, Tricks, and Yes, I Know Where the Bathrooms Are

I like to say I’m a “why” person. I want to know more than where your family wants to go. I want to understand the feeling you’re after. Are you trying to slow down and connect? Do your kids need nonstop action? Is this a big milestone trip where everything needs to feel special? Once I understand the why, I can fill in the details that make it feel right.

And I’m big on the small stuff. Bring snacks and flavored water drops for park days. Buy Memory Maker so you’re actually in the photos with your family. Strollers are necessary way longer than they are in real life, trust me. If your family is cruising, skip the buffet on embarkation day and find a sit-down restaurant instead. And if you’re visiting a destination without a theme park, book a local photographer for a short family session. It makes a better souvenir than anything you’ll find in a gift shop.

Oh, and I know where every bathroom is in every Disney park. It sounds trivial until you’re speed-walking through Adventureland with a potty-training toddler. Then it’s the most important tip anyone has ever given you.

Off the Clock

I live in Lewisville, Texas with my husband and our two kids. We’re a family that doesn’t sit still. Both of my kids were on their first airplane before they were four months old, and every school break means we’re going somewhere. My husband and I took our first vacation together very early in our relationship because I knew that being able to travel well together mattered.

One of my favorite memories is our first Disney Cruise Line sailing with my daughter. We went to pick her up from the nursery, and Rapunzel was rocking her in a rocking chair. We’ve been hooked on Disney cruises ever since.

A few other things about me: I went to a taping of The Mickey Mouse Club as a kid (yes, the Britney, Justin, Christina era). In college, our band played inside Disneyland and we entered from backstage by “it’s a small world.” And my husband proposed in the car on the way to Walt Disney World because he was too nervous he’d lose the ring if he waited to do it in front of the castle. So Disney has been woven into my life for a long time.

I was recognized as one of Disney’s 50 Teachers in 2021, which included time on Main Street before the park opened and being part of the parade. I was named Campus Teacher of the Year in 2025. And I’ve presented at the National Association for Gifted Children conference and the Texas Association for Gifted and Talented statewide conference multiple years running. I bring that same preparation and energy to every trip I plan.