Jenna Williamson
Travel Professional
Jenna is an aviation professional, road trip warrior, and trip planning aficionado born and raised in the Midwest. Previously a Disney Cast Member, she proudly considers the resort her true vacation home. Now residing on the East Coast, Jenna thrives putting her passions to use by creating travel plans that fulfill each unique explorer’s dreams. She prioritizes elements of fun and ease resulting in a truly magical experience for her clients.
Specializes in...
Walt Disney World
Disney Cruise Line
Universal Studios
All Inclusive
Virgin Voyages
Behind the Agent
Hi, Jenna! Tell us a little bit about yourself.
Hi! I’m Jenna and I am so excited to help you plan your next adventure. I currently live in Northern Virginia, but am a Wisconsin kid at heart. I have a passion for aviation and travel, so much so that I am a private pilot and have worked in the aviation industry for the last five years. I believe in the power of adventure – from the neighborhood coffee shop to a well planned trip to backyard shenanigans – there is always a surprise around the corner or a memory to be made. Adventure is where you are! In my spare time, I find joy exploring the east coast, taking spontaneous road trips, trying new restaurants, planning bucket list travel, and spending quality time with my family and friends.
If you could travel anywhere in the world, where would you go and why?
Everywhere! That has to be a valid answer – because picking one location is IMPOSSIBLE. If I were to start today though, I would begin by traveling the United States on an expansive road trip. It is my goal to visit every state and, as much as I love flying, I find beauty in visiting a city in the way people who live there primarily see it. I also enjoy the off-road adventures, hole-in-the-wall food stops, and impulse pull-offs to see some obscure sight or attraction. During my trip, I would be sure to try lots of local cuisine, visit historic sites and national parks, and send lots of postcards. After I complete my epic road adventure, I would hop on a plane with my sister and visit Italy for some delicious food and sightseeing. From there – the possibilities are endless!
Why did you become a travel planner?
I became a travel planner because I love travel and I really enjoy seeing others enjoy travel too. Handling the details and sorting out where to eat and what to see is genuinely fun for me and from local adventures to Disney, I was always getting asked questions about where I had been or was going. There was no better way to share my passion for these things than to step into the travel planner route.
What advice would you give someone going to Disney World for the first time?
Time is your friend! For almost all travel opportunities, having time before a trip will work in your favor. This is very true for Disney and I feel it is advice that expands across travel destinations. Having time allows you to plan, budget, save, build anticipation, and prep for changes. Spontaneous trips can be equally fun with practical expectations in place and, even then, timing can be everything!
What are three words to describe your travel style?
Say Yes. Try New Things. Embrace Adaptability. I know – those are more like mottos. Regardless, saying yes, to me, means assessing the options and saying yes to what serves your highest good. If that means saying yes to sleeping in – totally worth it. If that is saying yes to rope drop – race ya there. Say yes and do so without the shoulda, coulda, woulda’s holding you back. Every committed yes is a celebration. Try new things is pretty straight forward, yet many times when it comes to travel comfortability takes hold. I like to encourage a positive level of new into my travel style – new locations, new restaurants, new resorts, new shows – at least one thing new every trip, so I can continue to grow. Finally, embracing adaptability comes back to the idea that even the most perfectly plans have hiccups and that is okay. Every time the opportunity to adapt to a situation arises take advantage of that pivot – a happy surprise is around the corner. It is a new adventure.
What is your favorite Disney snack?
Adult Friendly Snack: Rum Pineapple Dole Whip Float (I mean is there really anything else worth getting). Child Friendly Snack: Pongu Pineapple Lumpia or Chocolate Dipped Pineapple (I am noting a pineapple theme here.) Overall, I am a foodie at heart, so please put me down for all snacks. I know I’ll need them to survive all the walking.