Hennebry Family 2026 Orlando Florida Disney Trip
Where do we even begin with our trip-of-a-lifetime?
Leanne and I have done lots of little getaways with our kiddos all throughout their lives—a quick hotel stay here, a small Airbnb there—but haven’t gone on a proper family vacation since before Walt was born (and maybe even Betty!). We’d figured it was about time despite feeling like the timing is never perfect (does one ever feel like you have enough money saved up before a vacation?? Sometimes you just gotta find a way, I suppose).
We departed our home in St. Thomas with a farewell from the Minnich side of the family (after a delicious lunch) and began what would become just shy of 28 hour of travel until we could check in to the condominium / timeshare that would be our home for the next 2 weeks. Situated just off the Magic Kingdom exit in Kissimmee, this unit was the perfect homebase for all of our Floridian adventures.
Our days were filled with tons of shopping (including multiple trips to Target, Walmart, Disney Springs, Universal City Walk, Primark, and beyond), a trip to the Peppa Pig Theme Park (highly recommended for families with kids ages 0 - 5; super affordable too!), tons and tons of Disney Resort exploring (with tons of transportation on the Skyliner, boats, busses, and monorail), a Princess dinner at the Grand Floridian resort and a walk through the Dezerland Automobile Museum (special date-nights out with mom and dad respectively), minigolfing at the Congo Mini Golf, and too many swims in the condo’s pool to count. Lazy days, fun days, and every day a hot day!
To say we had a great time would be the understatement of the century. These memories we will hold onto for the rest of our lives (also thanks to the magic of photography and cell phone cameras!!).
A special shout out to Leanne’s parents Don & Diane for allowing us to stay at their timeshare for 2 weeks. These photos are a testament to our appreciation for your gift!
All-in-all, we concluded the trip with almost 2,500 final edited photos (culled down from a starting 5,000+). Here are just 400 of our favourites (very hard to narrow down to!).
Aidan Hennebry is a marketing, sales, and leadership consultant based in Ontario, Canada. With over a decade of hands-on experience—ranging from $130M enterprises to early-stage startups—he helps companies align strategy with execution to drive real growth.