Jolene Wingerd

Jolene Wingerd is a Concierge Travel Advisor with Favorite Grampy Travels, specializing in Disney destinations including Walt Disney World and Disneyland, Universal Orlando, Universal Hollywood, and Disney Cruise Line, based in Baltimore, Maryland.

From “The Disney Friend” to Professional Planner

Before this became my career, I was the friend everyone called for Disney advice. Mapping out park days for fun, recommending restaurants, and helping troubleshoot itineraries just because I loved it. I wanted them to find the joy of the parks as much as I feel it.

The love and joy of helping others led me where I am now. I was continuously asked why I hadn’t become a travel agent yet. So I listened, and I joined Favorite Grampy Travels, a Universal U-Preferred Platinum agency and Authorized Disney Vacation Planner.

Making First Timers Feel Like Pros

Many of my Disney or Universal clients are first-time visitors or families who haven’t been in years and feel overwhelmed by how much has changed. Four Walt Disney World parks, three Universal Orlando parks, dozens of resorts, countless dining options, and Lightning Lane system that seems to change every few months. It’s a lot.

I specialize in family travel, multi-generational trips, and celebration travel — from birthdays to retirement surprises. One of my favorite client’s trip was helping to plan out an epic surprise where the retired guests’ family showed up to surprise them in the park.

Knowledge is Power

I’ve visited Walt Disney World more than 30 times and stayed at almost every resort, so my recommendations come from real experience, not just brochures. I’ve personally stayed at over 20 Walt Disney World resorts and only have a few left to complete the full list, so when I recommend a Disney property, it’s because I’ve walked those halls, eaten at those restaurants, and tested those bus routes myself.

After completing Disney’s training, College of Disney Knowledge, I came away with a sharper understanding of how each resort category fits different family sizes and budgets. It has expanded my knowledge of Disney destinations around the world, enabling me to better plan and personalize vacations.

With Universal, my specialist training for both Universal Orlando Resort and Universal Studios Hollywood gave me a detailed look at the various offerings at each destination. With Epic Universe now open, introducing five new worlds to Orlando, including The Wizarding World of Harry Potter: Ministry of Magic and SUPER NINTENDO WORLD, the planning landscape has gotten bigger and more complex. I’ve immersed myself in hands on experiences and dedicated a lot of time training with Universal. I can even say that I got to explore Epic Universe prior to its public opening, giving my clients an informed edge. Walking through this park with limited crowds gave me time to explore every world in detail, and that firsthand knowledge is something I bring to every client planning a Universal trip right now.

I’m also a Disney Cruise Line specialist. If you’re thinking about combining a park trip with a sailing, a Disney Cruise is hard to beat. A common misconception is that it is only for kids, however I’ve had so much fun as an adult. The entertainment, the dining rotations, and the level of detail on each ship is some of the best in the industry. The Disney Wish is our family’s absolute favorite, a luxurious fairy tale from bow to stern, but I’m keeping my eye on the new Disney Adventure, which launched from Singapore in March 2026 as the line’s largest ship yet.

Strategy That Makes a Difference

How you move through a park matters just as much as what you ride. I design park days that flow logically, minimize backtracking, keep your feet happy, and your family energized instead of exhausted.

Having experience personally with navigating food allergies, I know and understand how to plan safe, stress-free dining experiences at both Disney and Universal.

Planning for the Magic — and the Unexpected

Most people plan for sunshine. I’ve seen a trip through a hurricane.

I was at Walt Disney World when a storm shut down parks, evacuations, canceled dining reservations, and left families scrambling for answers. I stayed calm, adjusted plans on the fly, and learned something no certification could teach: how to pivot when a vacation doesn’t go as planned.

That experience shapes how I plan today. I don’t hand you an itinerary and disappear — I build flexible strategies and stay available before, during, and after your trip so you’re never navigating changes alone. Having someone in your corner who has been through a worst-case scenario on vacation and kept the magic going is key.

Why I Do This

My family is a happy little crew of three based in Baltimore, MD. I’ve been married to my husband for nearly 20 years, with a high school-aged son. We have big plans to eventually move closer to the parks in Florida, which tells you everything about how deep this runs. Florida is my home away from home. I visit multiple times a year to stay current on what’s new and what’s changing. Within my agency, I serve as our Disney Mentor, helping other advisors strengthen their expertise and knowledge on all things Disney.

Most importantly? I want you to enjoy the special moments. Vacations should feel magical. My goal is to make sure they stay that way.