Our 5-Day Disney World Adventure: Magic, Memories, and Family Fun

There’s nothing quite like Disney World. This September, our family enjoyed a 5-day trip filled with adventure, laughter, and plenty of magical moments. Traveling with our two-year-old grandson made the trip even more special, as we got to see the wonder of Disney through his eyes. We learned that taking a two-year-old has its challenges, but we would say that it was definitely worth it. Here’s a recap of our journey:

Day 1: Travel to Orlando

We flew United Airlines and were pleasantly surprised by the excellent service. Traveling with a toddler can be challenging, but the crew was kind and accommodating, making the trip smooth for everyone. After landing, we headed to our resort, eager to start our Disney adventure.

Day 2: Kennedy Space Center

Before diving into the parks, we spent a day at the Kennedy Space Center. It was inspiring to see rockets, learn about space exploration, and think about the vastness of our universe. A fun balance of science and awe before entering the world of Disney magic.

Day 3: Hollywood Studios – Toy Story Land

Hollywood Studios was a hit with our grandson, and we spent most of the day in Toy Story Land. The highlight was meeting Woody, Jessie, and Buzz Lightyear—his eyes lit up with pure joy! The rides and playful atmosphere were perfect for his age, and it gave us grown-ups a chance to enjoy the nostalgia, too. The best part is that our grandson had a free ticket (kids under three get in free!), so we did not feel the pressure to do it all.  We let our grandson spend as much time as he wants on his favorite activities. In this park, our grandson rode the Alien Swirling Saucers and Toy Story Mania.

Lunch was a Round Up Rodeo, which serves food family style, and is quick!

Day 4: Magic Kingdom – A Day of Pure Disney Magic

This was the heart of the trip: Magic Kingdom. We loved the fall decorations throughout the park—pumpkins, leaves, and festive touches everywhere. It felt cozy and enchanting all at once.

Our highlights:

• Meeting Mickey Mouse (a must for any trip!)

• Meeting Piglet, Winnie the Pooh, and Eeyore—a magical moment for all of us.

• Enjoying a Character Lunch at Crystal Palace, where our grandson got to interact with his favorite characters while we enjoyed a tasty meal.

• Rides: The favorite rides were the Mad Tea Party, the Railroad Train, and It's a Small World.

We also loved staying at the Grand Floridian Resort, where we could see the fireworks light up the sky right from the property. It was breathtaking and the perfect way to end the day.  Our grandson loved seeing the Monorail go by our room.  The Monorail had a substation right at the hotel and was only two stops from Magic Kingdom. The entire circle route takes 20 minutes.  We were also able to go from Magic Kingdom to the resort in a boat that let off at the harbor.  Another fun transportation route!

Meals Worth Mentioning

• Rainforest Cafe: Our grandson adored the indoor thunderstorms, animal animatronics, and fiery “eruptions.” The service was wonderful, and the experience was unforgettable. This is located in Disney Springs, which was a Monorail ride away!

• Crystal Palace: A standout for both food and the character experience—especially meeting Piglet and Pooh.  It is a buffet that makes getting food fast. That was important for our two-year-old, who goes from not hungry to hungry in seconds.  The characters came to our table, which was delightful. The photopass photographers were not at our lunch, so we had to take our own photos.

Day 5: Heading Home

After a magical trip, we flew back on United Airlines, again enjoying great service and a smooth experience.

Travel Tips That Made It Easier

• Stroller Rental: Renting a stroller for the entire week was a lifesaver. It made navigating the parks so much easier with a toddler.  We spent approximately $120 for the week.

• September Travel: Going in September, especially right after Labor Day, was a smart choice. The lower crowds meant shorter lines and more time for fun.  We never had to buy a Lightning Pass, which saved us money.

• Photopass: The photopass is definitely worth the cost.  For our two-year-old, having someone else get his attention was easier on all of us, and we got some fabulous Christmas-card-worthy photos! I purchased the $75 a day for two days. That was a cheaper option than buying Memory Maker.

• Overplan:  We planned more than we could possibly do, and then prioritized those events.  This helped us ensure that we stayed focused on what we truly valued and didn't get sidetracked into doing something we didn't care about.

Final Thoughts

Our 5-day Disney World adventure was filled with unforgettable moments—from meeting beloved characters to watching fireworks over the Grand Floridian Resort & Spa. Traveling with our grandson reminded us that Disney truly is for all ages. If you’re planning a trip, we highly recommend September for low crowds and cooler vibes, and don’t forget the stroller rental—it made all the difference.

Disney is more than a destination; it’s an experience that creates lifelong memories. And for us, this trip was pure magic.