Disney World-June 2026
Happy Monday, friends!
Today, I wanted to share all about our June trip to Walt Disney World!
Last month, we tagged along with John on one of his work trips to Orlando. The conference he was attending was at the Signia by Hilton Orlando Bonnet Creek, which is connected to the Waldorf Astoria Orlando. The second we found out he was staying at the Waldorf, we knew we had to come along!
We had actually just gotten home from Hawaii, made a quick three-day turnaround, and headed right back out on the road for Orlando. It sounds a little crazy, but we wouldn’t have had it any other way.
We absolutely love staying at the Waldorf Astoria Orlando. This was our third stay there in just six months, and it has quickly become one of our favorite places to stay when visiting Walt Disney World. Between the beautiful grounds, relaxing atmosphere, and convenient location, it feels like the perfect little getaway while still being just minutes from the Disney parks.
Day 1:
John spent the morning/early afternoon at work, so we got a later start on our drive to Orlando. We left home around 4:00 p.m. and didn’t arrive until just before 7:00 p.m. Let me tell you… I-275 and I-4 during late afternoon rush hour are no joke!
Thankfully, our room was ready when we arrived, and thanks to the Hilton app, we were able to skip the front desk altogether and head straight to our room. I always love it when check-in is that easy after a long drive.
After dropping off our bags, we wasted no time. We headed straight to Disney’s Hollywood Studios for a 7:30 pm dinner reservation at The Hollywood Brown Derby—our favorite restaurant in all of Walt Disney World! It’s become a tradition for us, and it’s one meal we look forward to every single trip.
After dinner, we wandered around Hollywood Studios and soaked up as much Disney magic as we could before the park closed for the night. There is just something so fun about strolling through the park after a great meal with no real agenda. Before we knew it, it was time to head back to the hotel and call it a night.
Day 2:
John spent the day at his conference and working in the hotel room, so the girls and I enjoyed a slow morning at the hotel. We had breakfast, relaxed in our room for a little while, and then made our way down to the pool.
One of the reasons we love staying at the Waldorf Astoria Orlando is the pool area. It is beautiful, relaxing, and the perfect place to spend a day away from the parks.
The girls, of course, made friends within minutes of getting in the pool, and I ended up chatting with a few other moms. One of my favorite parts of traveling is meeting people from all over the country. I always love hearing where they’re visiting from, what brought them to Orlando, and what fun adventures they have planned during their trip.
One of the highlights of the day was getting to have lunch with John. He was able to step away from his conference for a little while and meet us at the pool bar.
I ordered the caprese salad, the girls enjoyed the chicken tenders and fries, and I treated myself to a local craft beer. It was such a nice little break in the middle of his workday and gave us a chance to catch up before we all went our separate ways again.
After lunch, John headed back to his conference while the girls and I went upstairs to shower and get ready for an evening at Magic Kingdom. We were so excited to go to the Magic Kingdom that night! There’s just something about getting dressed for a Disney night that always feels exciting, no matter how many times we’ve been.
That evening, I made dinner reservations at the Grand Floridian Café. We had eaten there back in February and loved it so much that I couldn’t resist going back. Sometimes it’s fun to try somewhere new, but other times it’s nice to revisit a favorite you know your family will enjoy.
We took an Uber over to Disney’s Grand Floridian Resort & Spa for dinner, which also made getting to Magic Kingdom afterward incredibly easy. After our meal, we hopped on the monorail and were at the park in just a few minutes.
Before our trip, I had booked Lightning Lanes for the evening, so as soon as we walked into Magic Kingdom, we were able to start checking rides off our list. We bounced from attraction to attraction and made the most of every minute we had in the park.
I honestly thought we’d leave around 9:00 p.m. since we’d had such a full day, but we ended up staying until almost 10:30! It was such a fun night and a perfect way to end the day!
Day 3:
The next morning, John was up before the girls and me and picked up breakfast for all of us. He brought back bagels, pastries, and delicious coffee, so breakfast was ready as soon as we woke up.
I’m always thankful when he gets up early and grabs breakfast (or at least coffee!) before the girls and I are awake. It makes our mornings so much easier, especially on vacation.
Thankfully, I called that morning to see if we could get a late checkout, and they said yes! The girls and I were so excited. We took full advantage of the extra time and headed down to the pool for one last swim before making the drive home.
While we were at the pool, John wrapped up a little more work in the room. Being a lawyer, there’s always another email to answer or something that needs his attention, so it worked out perfectly.
After one last swim, we headed back upstairs to shower, pack up our things, and start the drive home.
I’m really glad we decided to tag along on this work trip. I wasn’t sure how we’d feel after just getting back from Hawaii, but it ended up being such a fun little getaway. It gave us a few extra days together as a family and was the perfect way to ease ourselves back into mainland living. 😂
Overall, we had such a fun few days in Orlando! It was nice to slow down, enjoy one of our favorite hotels, spend some time at the pool, and squeeze in a couple of evenings at Disney.
I’m really glad we decided to tag along with John on this work trip. It ended up being the perfect little getaway before getting back into our normal routine after Hawaii. Sometimes the unplanned trips end up being the most fun.
Until next time, Orlando!
-Holley
