Kissimmee, Florida
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Timeless Kissimmee

Kids of all ages are welcome in Central Florida

Steve’s parents had just retired to their old stomping ground, Central Florida, and the boys were practically buzzing with excitement to visit. And who could blame them—we’d all heard countless stories about Steve’s family vacations in Kissimmee. We were eager to experience the spot where the action happened. The fact my in-laws enjoyed Kissimmee enough in their younger years to come back in their senior years spoke volumes about the city’s ability to entertain toddlers to elders.

Visiting the locals

Before venturing into Gatorland, we posed at the entrance for our vacation’s first family photo. Like the alligator head near the entrance, the inside of Gatorland was designed to impress and immerse. Walkways snaked into the lush humid heart of gator habitat. The first animals that greeted us, however, were birds. They didn’t seem to mind living in the alligator capital of the world. Steve’s mom, Diane, the textbook definition of a birder, pointed out a heron catching a ride on a swimming gator’s back. “Bird-Uber!” laughed seven-year-old Bo. “Charlie-Uber” proclaimed his brother, pointing in another direction. Naturally, the five-year-old was the first to spot the Gatorland Express railroad.

Since it looked like an efficient way to see the expansive park and get our bearings, we boarded the red and white open-air train. Minutes after departing the station, our conductor had taken us all the way back to 1949, when Gatorland was founded. The adults loved hearing about the history of the park and viewing the animal enclosures from the comfort of a shaded, mobile enclosure. The boys loved the conductor’s jokes. He had them on the lookout for Bigfoot within minutes.

Gators performing at Gatorland in Kissimmee, Florida
The original entrance to Gatorland in Kissimmee, Florida
A rookery bird at Gatorland in Kissimmee, Florida
View of the lake at Gatorland in Kissimmee, Florida
The Screamin Gator Zip Line at Gatorland in Kissimmee, Florida

Gatorland also has a zipline course, splash park, and aviary, but we started with its namesakes. Some of the alligators had innocuous names: Buster, Morton, Blondie, and Pearl, the rare albino alligator who’s made international headlines. Others had more sinister names: Blackwater, Sultan, Will E. Bites, and Bonecrusher II. “He’s a descendent of Bonecrusher,” said Steve Sr. “Back in my day, Bonecrusher was advertised as the world’s largest alligator.” I wasn’t surprised he remembered that. My father-in-law has the memory of an elephant. But, I was kind of surprised that more than 50 years later, and despite all of our new digital distractions, we were still here, awed by the size of alligators in the same way my husband and his parents have been for decades.

After applauding for the reptilian athletes of the Gator Jumparoo Show, we ended the afternoon with a bite to eat. Charlie and Bo dangled fishing poles, baited with turkey sausages, in front of their new friends whose giant jaws swallowed the sausages whole.

Soaring back in time

“World. Upside. Down.” Steve stammered breathlessly the next day, climbing out of the plane’s front seat. The rest of us had watched from the ground as the vintage T-6 Texan turned nose over tail and performed other stomach-churning aerobatic stunts, usually reserved for air shows. “I can’t believe you gave me the controls!” Steve said to his flight instructor who just smiled. “And I can’t believe you used to fly that.” Steve said, now looking at his dad, an Air Force veteran. “We all trained in the T-6,” Steve Sr. said proudly. At Warbird Adventures, a flight school and air museum, the whole family experienced something new: watching Steve zoom high above in a vintage plane.

The Tico Belle at Warbird Adventures in Kissimmee, Florida
Warbird Adventures takes you to the past in vintage warplanes.

Trading the runway for its huge hangar, we admired the “working” museum filled with a retired warplanes collection. It was nice to see that in the age of jumbo jets and drones, there was still a place to experience their predecessors. It was also great to have Steve’s dad with us to talk about his experience in the Air Force (and answer all his grandsons’ questions). Hearing Steve chime in with details of his flight was a special father-son bonding. “Exactly 20 years ago we came up with the idea for this museum,” said Thom, one of Warbird Adventures’ founders. Given their collection, and assuming they could find similarly passionate people to hand the controls to, I wouldn’t be surprised if it was around for another 50 years.

Treating our taste buds

“Do you think astronauts can see it from space?” Diane asked the boys the next morning when we pulled into the parking lot of the “world’s largest orange.” The 92-foot long, 18-ton Orange World was clearly designed to be a roadside attraction. According to Steve Sr., it was the first gift shop on Highway 192 when it opened in 1973. More than 40 years later, it was still turning heads for its size and the allure of the sweetness within. “The Florida oranges taste like summer vacation to me,” Steve said. “Who wants some?!” he excitedly asked Charlie and Bo, who responded with cheers.

Inside, the shrine to Florida’s state fruit continued in a maze of crates overflowing with colorful citrus. “That’s called Buddha’s hand,” said an employee, noticing Charlie staring at a yellow fruit with gnarly fingers. Sampling our way through the store, we tasted tangelos, pomelos, marmalades, honeys, and when we couldn’t take any more sweetness, hot sauces.

“Generous portions of creamy soft-serve were handed to us out of the same windows welcoming the masses since 1983.”

Three miles later, we were craving sweetness again. Fortunately, Kissimmee is home to America’s first Twistee Treat: a two-story ice cream cone that could feed half of Florida. Generous portions of creamy soft-serve were handed to us out of the same windows welcoming the masses since 1983. We all laughed when Diane started to ask for “the usual” before remembering the servers had changed. Fortunately, they guessed she was a swirl-in-a-cup fan. This wasn´t their first rodeo. It wasn’t Steve Sr.’s either. He pointed out how Twistee Treat breaks tradition by putting its sundae peanuts below, not atop, the whipped cream. “It makes less of a mess,” he said, winking at his sprinkle-faced grandsons.

Cruising through the ages  

Later, it was time for some fun with four wheels. With hundreds of cars polished to perfection, Old Town Kissimmee looked like the dealership for dealerships. Museum meets parade, the Saturday Nite Classic Car Show and Cruise is America’s longest running weekly car show. One of the most committed cruisers even drove during Hurricane Charley to keep tradition alive. As we strolled along the walking street, Steve Jr. and Sr. bent their heads under the hoods of everything from a 1969 Ford Mustang to a 1936 Chrysler Airstream and an immaculately restored 1925 Model T. Ford, pointing out shiny features to Charlie and Bo. Diane tried to teach the boys “the twist” in front of Trophy Row where a live band was cranking out 60s classics. They thought it was wacky, but they danced and laughed anyway. Music is a universal language, and here in Old Town Kissimmee, I watched as it bridged the decades between grandmother and grandsons. And father and son…

By the time the last car honked farewell and the final notes of Fortunate Son played, it was 11 p.m.—long past the fading boys’ and their yawning grandparents’ bedtimes. But, I realized, they weren’t too young or too old for this vacation. Kissimmee is an ageless place.

You’re not human if you don’t get tired from so much timeless fun.

A classic red car at the Old Town Kissimmee Car Show in Florida
Mel's Drive In at the Old Town Kissimmee Car Show
A young woman in Old Town Kissimmee, Florida
A classic yellow corvette at the Old Town Kissimmee Car Show in Florida
A young woman in front of a classic car at the Old Town Kissimmee Car Show in Florida
We Make 'Cruising through history' Vacations