12 Things to Do in Kissimmee

The enormous Lake Tohopekaliga fringes the city of Kissimmee, with the Kissimmee Lakefront Park as an expansive, attractive spot from which to watch the area wake up in the morning.

There’s plenty to see and do by the lake, whether you head out on a jogging or biking trail, or simply find a peaceful spot to sit and indulge in some people watching. Later in the day, you can find deckchairs from which to soak up some rays, together with barbecues and picnic areas where you can have a feast with the family.

Heading out by Segway in Kissimmee might be one of the more fun and adrenaline-boosting ways to take in the sights of Osceola County – it’s certainly edgier than most of the city tours available. 

Taking a ride on Zero Emission Tours’ Segways gives you an intimate feel for the sights and sounds of Celebration, a planned community originally designed by Disney some 12 miles from Kissimmee proper. There are nature, great scenery, and local villages to see along the way here, and it all starts with an instruction session on how to safely ride your Segway.

Lake Toho is known for its vast stocks of fish, particularly seabass, but it’s just one of several bodies of water in the area that are prime spots for rewarding fishing adventures. 

By taking a trip out onto the Kissimmee Chain of Lakes with a local guide from tours like Fish Orlando, you’ll discover the best locations for securing an abundant catch. You’ll also get to pick up the tricks of the trade when it comes to successful bass fishing, and of course, take in the area’s beautiful marine scenery.

If simply flying in an authentically vintage aeroplane isn’t enough for the most hardcore of aviation geeks, then Stallion 51 at Kissimmee Gateway Airport is the place to head to. 

The adventure here doesn’t stop at simply gawking at or even taking a ride in one of the flight school’s aircraft – you can be up front helping the aircraft to glide through the sky. At Stallion 51, you can take full-on pilot training courses, ride as a passenger, or simply watch and admire the planes passing by.

The Monument of States in Kissimmee’s Lakefront Park dates back to WWII when, in the aftermath of Pearl Harbor, a local doctor procured local rocks and fossils from each of the then 48 US states. Assembled into a tower with each rock labelled according to its origin, the monument was designed to demonstrate national unity. 

That sense of unity is certainly conveyed by the fact that the monument – now in the National Register of Historic Places – was assembled entirely by volunteers. You can see their names etched into the pavement alongside it.

Soldiers of the past and present are honoured at Kissimmee’s Museum of Military History. The museum aims at ‘educating the world about the cost of freedom’. This isn’t a war-glorifying attraction, but rather somewhere seeking to increase awareness of the realities of war and of the experiences of the American armed forces. 

The museum’s rotating exhibits depict the various conflicts the US has been involved in over time. There are the likes of military uniforms, old photos and personal retellings of wartime experiences, tanks and vehicles, and weapons on show. 

Kissimmee isn’t short of opportunities for good old-fashioned retail therapy, and some of the city’s best is at the Old Town outdoor shopping centre. This long-running mall is a vintage-style depiction of a classic Florida town, harking back to ‘when times were a little simpler’. 

There are more than 70 boutiques on offer, touting everything from clothing and gifts – souvenirs that you can’t get anywhere else, they say – to pampering spa experiences. When the little ones need entertaining, there are also family-friendly restaurants and theme-park-style rides on hand.

Committed chocoholics, eat your hearts out: Chocolate Kingdom is both a museum and factory in Kissimmee that’s dedicated to everything cocoa-related. If you have a favourite, be it dark chocolate or with cashews or caramel, you can see how it’s made right here. 

Take a tour at Chocolate Kingdom and in 45 minutes you’ll have walked through every step of the chocolate production process, from bean to bar – with an added fantasy twist to bring the whole experience to life even more. You can even go the whole hog and make your own customised chocolate bar to take home.

Thrilling live entertainment dinner experiences await at dinner places in Kissimmee like the Medieval Times Dinner & Tournament. With all Kissimmee’s and Orlando’s theme parks, it’s clear the area has a talent for a touch of make-believe. 

At Medieval Times Dinner & Tournament you’ll be transported back to the Middle Ages, where actors in full chivalrous armour engage in a swordfight or mount horses for jousting bouts. You and family can cheer on your side in battle while you use only your hands to devour a rustic olde-worlde 4-course meal. Showtimes are 6pm and 8.30pm.

Escape to Eleven – an apt name for a restaurant and bar on the 11th floor of the Reunion Resort – is a place to end the night in style. Surely, every trip to Florida needs a touch of glitz, and a getaway to this top spot in Kissimmee is no exception. 

The steak is the main attraction here, but those in the know also come to sip sundowners on the rooftop veranda – whether that's a historic cocktail or one of the bar’s modern interpretations. Stay long enough to be in for a killer view of the nightly fireworks display put on at the Magic Kingdom just next door.

Main Gate Flea Market is filled with thousands of unique items for shoppers looking for bargain souvenirs and gifts. You really can shop until you drop at this top flea market in the Orlando area, and the sheer range of items on offer will keep you entertained even if you don’t intend to buy!

The main reason most visitors to Orlando come to shop here is because of the wide range of branded memorabilia from Disney and Universal, available at cheaper prices than you'll find within the theme parks.

The Suhls Rodeo at Kissimmee Sports Arena is known as "The Greatest Show on Dirt". Cowboys and cowgirls from all over Central Florida participate in several events a month to compete for glory (and quite a lot of money).

Each competition is real and unrehearsed. They host bull riding, barrel racing, bucking broncos and calf roping. You'll even see rodeo clowns! The events are a look into the life of a cowboy (or cowgirl) and are today's link to the heritage of the Wild West.