a gator hatchling in a tank at the Osceola County History Center

How To Experience Kissimmee If You Don’t Love Theme Parks

a taxidermied hog in the Osceola County History Center — Experience Kissimmee
Not the kind of wildlife some people expect to experience in Kissimmee, yet here he is. Or she. I didn’t check.
Photo by Cathy Salustri

In college, I lived oh-so-briefly in Kissimmee. It was quite the experience.

The Kissimmee Experiment (1994)

Despite attending UCF (go Knights!), I moved to the Kissimmee area because I had a part-time job at Disney and the commute from my apartment in Winter Park to Lake Buena Vista was not… ideal. Orlando, the saying goes, is an hour from Orlando — and neither Winter Park nor Lake Buena Vista were technically in Orlando.

In the early- and mid-90s, Kissimmee had a lot of “dinner-and-show” experiences, likely spurred by the popularity of Medieval Times. I never set foot in any of them while I lived there.  Kissimmee was close to my part-time job (which, at the time, was a lot more fun than some of the courses I had to take outside my major), and that was all that mattered.

On occasion, I would meander outside the touristy areas. I remember a lovely downtown that had almost no one wearing a Mickey Mouse t-shirt and a flea market in the St. Cloud area. A lot about this time in my life — my early twenties — is blurry now (for a lot of reasons but most of which I should work out in therapy, not here, so let’s move on, shall we?), but when, a few months into what I can only call the Kissimmee Experiment, I moved back to the coast, I wasn’t thrilled to leave Central Florida but I was definitely OK with losing the dinner-and-show vibe.

Experience Kissimmee (2024)

A few weeks ago, I decided to revisit Kissimmee. I wanted to see what I could find beneath the tourist veneer.

There’s plenty; so much so that I expect we’ll make another trip out there soon, because once you start looking at the area not as a tourist, but as someone who loves Florida, there’s plenty to experience in Kissimmee.

a gator hatchling in a tank at the Osceola County History Center
This little guy was quite real — and quite annoyed by my presence.
Photo by Cathy Salustri

Top Three Kissimmee Experiences

  1. Osceola County History Center
    I cannot say enough about how well done this history center is. They start with pre-EuroAmerican history and move through present-day. You’ll find kid-friendly and adult-sensitive exhibits, respectable representation of Black Floridians, and nature education. Overall, it’s a top-notch experience for history buffs.
  2. Woodsby’s Cafe
    Woodsby’s took us about 20 minutes away from our resort, and about twice as far, metaphorically, from the tourists. I hope you listen to the podcast to hear what a visit here taught me about believing Florida’s mainstream media press, but if you don’t, know that I had a wonderful experience and a wonderful meal in a diverse, welcoming environment.
  3. Downtown Kissimmee
    Once again, real life trumps the idea that Florida doesn’t have history. Antebellum architecture and a sense of place pervade.

Kissimmee Lodging

Legacy Vacations hosted us (and the dogs) at one of their one-bedroom suites. My honest take: It’s comfortable, well-appointed, diverse, and committed to sustainability. The units aren’t new, but they’re well-maintained, and if I had kids, I’d easily book a week here and never leave the property.  It’s farther than you’d think from Disney, but most of the people there didn’t seem interested in Disney. Perfect for families, comfortable enough for couples, and at the end of the day, I’m happy to show love to a B Corp committed to making a difference in the world.

How To Do Kissimmee: The Podcast

Here’s the podcast Rick and I recorded about the Osceola County History Center, paddling the headwaters to the Everglades at Shingle Creek, and so many other things you can do there that don’t require theme park admission.

Get More Florida!

Finally, if you love Florida, please support my Florida travel habit, my dogs, and this website. Here’s how: