Well Hello Magic: A Disney Planning & Experience Podcast
Jessica Mickelson is the voice behind Well Hello Magic, a Disney-loving mom of four, former therapist, podcast host, content creator, and trusted expert in Disney vacation planning for families, moms, and first-time travelers. She is also part of a proud military family, bringing an added layer of understanding to planning trips around real-life schedules, budgets, and seasons of change.
A lifelong Disney fan raised on Main Street magic and Mickey-shaped memories, Jessica helps families confidently plan trips to Walt Disney World, Disneyland, and Disney Cruise Line without overwhelm, burnout, or blowing the budget. Her approach to Disney trip planning focuses on realistic expectations, thoughtful strategies, and creating meaningful experiences that work for real families.
As a mom who has done Disney with toddlers, teens, grandparents, large groups, and multigenerational families, Jessica shares real-world Disney planning advice rooted in emotional insight and hands-on experience. From stroller-friendly itineraries to thrill-ride strategies, from solo trips to girls’ weekends and group vacations of 14 or more, she gives listeners the tools to plan Disney vacations that feel magical and manageable.
On the Well Hello Magic podcast, Jessica shares Disney vacation tips, park planning strategies, Lightning Lane guidance, event guides like Mickey’s Not-So-Scary Halloween Party and Mickey’s Very Merry Christmas Party, and honest reflections on the emotional side of Disney travel. Episodes feature expert guests and fellow Disney-loving moms who understand the balance between preparation, flexibility, and enjoying the moment.
Beyond the podcast, Jessica creates daily Disney and family travel content on Instagram and YouTube, blending humor, helpful hacks, and heartfelt storytelling into practical videos for Disney travelers at every stage of life.
Well Hello Magic: A Disney Planning & Experience Podcast
094: How We Conquered the Four Park Challenge at Walt Disney World — With Kids, Grandparents, and Zero Regrets!
Ever wondered if you could visit all four Walt Disney World theme parks in one day with kids, teens, and grandparents in tow? In this episode of Well Hello Magic: The Podcast, I’m walking you through every magical (and exhausting) step of our family’s Four Park Challenge to celebrate my niece’s birthday.
From rope drop at Animal Kingdom at 7:00 AM to leaving Magic Kingdom at 1:00 AM, we tackled 17 attractions, dined at 5 different locations, and covered over 12.5 miles. Whether you’re wondering if this challenge is even possible with little ones or looking for a step-by-step breakdown on how to plan your own Disney park-hopping day, this episode is packed with everything you need to know.
✨ In this episode, I break down:
- How to plan a Four Park Challenge with kids of different ages
- The best route and park order to make your day efficient
- How to use Lightning Lane to save time on the most popular rides
- What to pack to survive 18 hours in the parks
- When to rest, when to push through, and when snacks save the day
- How to involve grandparents and still keep the day manageable
- Why renting a stroller was essential even for our older kids
You’ll get our full itinerary what time we entered each park, which rides we hit, how we handled mealtimes, and how we made it feel magical for every generation. From Kilimanjaro Safaris and Guardians of the Galaxy to Mickey & Minnie’s Runaway Railway and ending with TRON and Barnstormer at midnight, this was a day we’ll never forget.
Meanwhile, our littlest traveler enjoyed a slower-paced day back at the resort with the grandparents and yes, that was part of our strategy too. This challenge doesn’t have to mean dragging toddlers through the entire experience. In fact, I’ll talk about how you can plan your own Four Park Challenge while splitting the day to fit your family’s unique needs.
You’ll hear:
- How to do a Four Park Challenge at Walt Disney World with kids
- The most efficient way to park hop using Disney transportation
- When to schedule your Lightning Lanes and what to skip
- Why EPCOT’s International Gateway and the Skyliner are key to saving time
- Tips for squeezing in thrill rides
- Where to eat fast, what snacks to grab, and why cinnamon rolls after 10 PM taste better
- How to still enjoy fireworks, parades, and character photos without burning out
Final stats from our Four Park Challenge:
- 17 attractions
- 5 dining stops
- 29,431 steps
- 12.63 miles
- Countless memories made
This is a real, honest look at how a family can take on the Four Park Challenge and make it work even when you're tired, it rains, or your daughter needs a stroller at hour 14. No highlight reel here, just the real magic.
Tune in now on your favorite podcast app and follow @wellhellomagic on Instagram for more family Disney tips, park strategy breakdowns, and how to ke
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