Kissimmee, Florida is often referred to as a suburb of Orlando, but it’s much more than that. The city was founded in the 1800s through the arrival of steamboats on the Kissimmee River. A railroad later came to town, making it a transportation hub.
The local economy relied heavily on farming and cattle ranching until Walt Disney World opened in 1971, shifting it to tourism. Today it’s accessible via Amtrak and SunRail as well as flights to Orlando’s airports.
This post contains affiliate links that earn income through purchases but don’t charge you an added fee.
Soar through the trees with the greatest of ease at one of Kissimmee’s zipline courses. Orlando Tree Trek was our favorite, which includes multiple ropes courses of varying difficulty levels. Entry includes all the gear you need like harnesses and gloves.
Book your Orlando Tree Trek Adventure Park excursion here.
Ride in an airboat
The Everglades isn’t the only place for airboats! Kissimmee has operators running airboat tours like Boggy Creek Airboat Rides. You never know what wildlife you might see, but alligators are almost guaranteed. They also have gold mining, a Native American interpreter, alligators, and a cafe.
Dine on authentic international food
Florida has a number of different areas known for international cuisine including Miami‘s Little Havana and Tampa’s Ybor City. But Kissimmee also has flavors from around the world. Buchito has Cuban-style sandwiches while a shop down the street has delicious fruit sorbets.
Admire quirky landmarks
Roadside attractions are found throughout the nation and Kissimmee is no different. The Monument of States was thought up after the bombing of Pearl Harbor by a local doctor looking to promote tourism. Citizens of many states, and later countries, sent rocks to be added to the monument.
Chow down at celebrity chef restaurants
Orlando and Kissimmee may not be what you think of in terms of celebrity chef restaurants, but you’d be wrong. Disney Springs, formerly Downtown Disney at Walt Disney World, is north of Kissimmee and contains multiple restaurants run by notable chefs like Art Smith, Rick Bayless, and Jose Andres, who opened Jaleo, a Spanish restaurant pictured above.
Visit a winery
Florida may not be on your radar for wine. But Island Grove Winery is just down the street from the Margaritaville Resort and has a full restaurant and wine shop.
Purchase wine-themed gifts and sample wines by the glass using their card system. Enjoy a bottle outside with friends if time allows!
Go bass fishing
Lake Tohopekaliga, often called “Lake Toho,” is a large lake near downtown Kissimmee. Parts of it are where airboat tours leave from.
But others are popular with bass fishermen. Big Toho Marina is the best place to get outfitted for your day on the water and to put in your boat.
Book a Half Day Lake Toho Fishing Trip near Kissimmee here.
Believe it or not, much of the area outside of Orlando is farms and countryside. That makes it ideal for outdoor recreation, including horseback riding. Lazy H Ranch is just one of the farms that offer trail rides for all ages and experience levels.
Pick oranges at a citrus farm
There’s a reason that Florida is known for its orange juice! The Sunshine State has citrus farms throughout the region producing oranges and grapefruits. Showcase of Citrus is a 2,500-acre facility with U-Pick, wine tastings, rides through the fields, and farm animals.
Step back in time at Pioneer Village at Shingle Creek
Osceola County has a rich history which is demonstrated at Shingle Creek. The living history park has a permanent collection of buildings from the period that interpret what life was like in early Florida. They offer both guided and self-guided tours.
Stay in incredible accommodations
The theme parks of Orlando have some incredible hotels with their own benefits. But staying in Kissimmee provides additional value, especially for larger groups.
Margaritaville Orlando Resort has resort rooms and cottages as well as restaurants, pools, a water park, and other amenities. Banyan Hotel & Microsuites has casual rooms with kitchenettes and an onsite pool. Diamond Resorts has a number of rentals right outside the theme parks, including Parkway International Resort and Barefoot’n Resort.
The homes at Reunion Resort are top of the line, especially the themed vacation rentals. For example, the sprawling Legends Palace has a Harry Potter suite behind a sliding bookcase. It also has a pool and basement bowling alley! The resort also has neighborhoods within it like The Bear’s Den at Reunion Resort.
My stay in Kissimmee was arranged by Experience Kissimmee.