Top 4 Things to Do in Downtown Kissimmee for First-Time Visitors

Start your day with a bit of sunshine and a lot of scenery. Lakefront Park, sitting right on the shores of Big Toho (that’s Lake Tohopekaliga for the newcomers), is where natural beauty meets endless activities. 

Kick things off with a slow walk along the paved flat paths that loop around the lake. The area is wheelchair- and stroller-friendly, with several parking spots available throughout the park, making exploration a breeze.

Don’t miss the playground if you’ve got little ones in tow. With four epic slides sized just right for every kind of climber, it’s a guaranteed way for little ones to burn some energy while you relax on a nearby bench.

And when it’s time to refuel, the Veteran’s Lawn is perfect for a laid-back picnic. Find a shady bench or spread out a blanket and let the lake breeze work its magic. You’ll hear birds calling overhead, palm trees swaying softly, and watch the sunlight shimmering on Big Toho’s peaceful waters.

Downtown Kissimmee wears its history proudly. As you wander through its brick-lined streets, you’ll find touches of the past around every corner. From historic buildings and vintage signs to hidden plaques honoring local legends, this area blends heritage with charm. It’s this mix of stories and style that gives Downtown Kissimmee its one-of-a-kind personality.

One landmark you won’t want to miss is the Monument of States. Built in the 1940s as a symbol of unity during World War II, this colorful tower was created using stones sent from every U.S. state, along with a few international contributions. The result is a one-of-a-kind structure that’s both meaningful and eye-catching.

Snap a selfie, then take a moment to read the plaques and discover the stories behind the stones that make this monument so special

Downtown Kissimmee is bursting with flavor, and no matter what you’re craving, there’s something tasty waiting around every corner. In the mood for smoky, all-American BBQ? Big John’s Rockin’ BBQ is the place to be. More of a sushi fan? Head to 3 Sisters Speakeasy for creative rolls and cozy vibes.

But one spot we love is Willy’s Wieners. It’s fun, affordable and perfect for families with accessible parking right out front. Featuring twenty specialty hot dogs on the menu, you just might find your next favorite combo. 

We’re big fans of the classic Chicago dog with tangy pickles and that satisfying snap in every bite. Pair it with a fizzy gourmet grape soda, a Willy’s exclusive that tastes just like childhood in a bottle.

And don’t even think about skipping the funnel cake fries! Grab a bench outside, enjoy the breeze, and soak up the downtown vibe one sweet bite at a time. Fair warning: may cause accidental sharing.