Blake Walsh

15 Best Things to Do in Kissimmee, FL

  • Published 2022/10/20

When you think about Florida, the first place that pops into your head is probably Orlando due to the plenty of amusement parks.

But its neighboring city, Kissimmee, should not be overlooked.

As the county seat of Osceola County and its largest city, Kissimmee has a population of 79,226 as of the 2020 census.

It is a city that provides tourists with a classic Florida experience.

It has a plethora of indoor and outdoor recreational spots, such as historic sites, nature preserves and parks, and more!

Most notably, you can find the Monument of States, a symbol of the nation’s unity and camaraderie.

Experience the best of Florida by checking out the 15 best things to do in Kissimmee, Florida!

Experience One of America’s Great Outdoors at Shingle Creek Regional Park

Kayaking at Shingle Creek Regional Park

Jeff Holcombe /

Shingle Creek Regional Park is a beautiful open space in Kissimmee, regarded by former President Obama as one of “America’s Great Outdoors.”

Shingle Creek Regional Park is a unique recreational area comprising multiple parks, each with its own beauty and adventure.

There’s the Ruba area on U.S. Highway 192 & Yates Road, a 16-acre space with scenic views of Shingle Creek.

The Bass Road location provides the community with recreational opportunities and a safe home for the endangered Gopher Tortoise.

Steffe Landing on West Vine Street is great for water-related activities such as fishing, kayaking, and canoeing.

Great heron perched on a tree at Shingle Creek Regional Park

Jeff Holcombe /

If you’re into historical structures, you should head to the park’s Steffe Homestead, which features a historical home built in the early 1900s.

The Pioneer Village on Babb Road will also satisfy your cravings for historic sites as it shows how life was lived in the 1900s.

For your picnicking needs, head to Marsh Landing on Marsh Road.

Overall, Shingle Creek Regional Park has a lot to offer, so make sure to stop by its multiple locations.

A cabin at Shingle Creek Regional Park

Fredlyfish4, CC BY-SA 4.0, via Wikimedia Commons

Discover Osceola County’s History at the Osceola County Welcome Center & History Museum

The Osceola County Welcome Center & History Museum is a great place to learn more about the fantastic history of Osceola County.

Located on West Vine Street, The Osceola County Welcome Center & History Museum showcases the county’s diverse habitats and rich history with interactive displays.

The Welcome Center features realistic dioramas of the different habitats in the county, such as swamplands, pine flatwoods, oak hammocks, and lakefront.

The History Museum exhibits remnants of the citrus and cattle industries, transportation, and early tourism in Osceola County.

The site also has a porch that lets you experience the picturesque view of Shingle Creek.

The Osceola County Welcome Center & History Museum is a must-visit in Kissimmee, so make sure to stop by!

Learn about the American-Filipino Relationship at the Bataan-Corregidor Memorial

The Bataan-Corregidor Memorial is a monument in honor of the soldiers who suffered during the war against the Japanese in the Philippines.

The Bataan-Corregidor Memorial was the brainchild of former Filipino diplomat Menandro M. de Mesa and City Commissioner Richard Herring.

They were concerned about the lack of recognition for those who went through the Bataan Death March, a grueling 65-mile march without food, water, and rest.

In order to recognize their courage, they decided to build a memorial with the help of sculptor Sandra M. Storm.

The memorial features a sculpture of a Filipino woman offering water to a Filipino and American soldier.

It serves as a reminder of the two countries’ unity through difficult times.

Visit the Bataan-Corregidor Memorial nestled in Kissimmee Lakefront Park on East Monument Avenue.

Enjoy Great Medieval Food and Theatrics at Medieval Times Dinner & Tournament Events

Medieval Times Dinner & Tournament Events offers a unique experience unlike any other in the city of Kissimmee.

Medieval Times Dinner & Tournament Events is one of the most entertaining dinner theaters in the entire country.

The theater boasts an amazing 11th-century-style castle complete with suits of armor, stand guards, and items showcasing Medieval Spain.

You’ll also get the opportunity to join the pre-show knighting ceremony and meet the majestic animals participating in the show.

They also have a gift shop with a wide selection of fun items, including an array of medieval swords and other weapons.

For the main attraction, they host an incredible jousting event with knights, horses, falcons, and more!

During the show, you’ll get to feast on the castle’s delicious four-course meal thanks to the generosity of Queen Maria Isabella.

Experience this one-of-a-kind dinner theater at Medieval Times Dinner & Tournament Events on West Vine Street.

Visit the Country’s Symbol of Unity at the Monument of States

Daytime view of the Monument of States

Visitor7, CC BY-SA 3.0, via Wikimedia Commons

The Monument of States is one of the world’s most unique monuments as it showcases the national unity of America.

Located on East Monument Avenue near Kissimmee Lakefront Park, the Monument of States is made up of stones sourced from the nation’s 50 states.

Each stone represents the beauty and traits of the state they came from.

Dr. Charles Bressler-Pettis was the founder of this monument.

Base of the Monument of States

Visitor7, CC BY-SA 3.0, via Wikimedia Commons

He originally planned to construct it to boost the county’s tourism.

But the Pearl Harbor attack made him realize the country needed a symbol for everyone to unite, so he started accelerating the monument’s construction.

Today, the site of the monument is a well-known recreational spot, but the Monument of States still serves as the country’s symbol of unity.

Top part of the Monument of States

Visitor7, CC BY-SA 3.0, via Wikimedia Commons

Have Dinner with the Mafia at Capone’s Dinner & Show

Capone’s Dinner & Show is another unique dining establishment in Kissimmee.

Unlike the previous entry, Capone’s Dinner & Show is a dinner theater that hosts a 1930’s gangland Chicago-themed show.

Instead of knights and swords, you’ll meet with ferocious gang members and guns.

Want to know what it feels like to be part of them?

You can buy a fedora and other paraphernalia in their gift shop.

As you enjoy the entertainment, you’ll get to feast on an amazing Italian-American buffet.

Capone’s Dinner & Show is on West Irlo Bronson Memorial Highway, so make sure to visit them!

Go on a Real Florida Adventure at Orlando Airboat Tours

The state of Florida is full of amazing outdoor experiences.

In Kissimmee, the best place to experience a real Florida adventure is Orlando Airboat Tours.

Orlando Airboat Tours specializes in conducting tours of the Everglades with their state-of-the-art airboats.

These airboats are smaller in size compared to barge-type boats, so you can get into every nook and cranny of the Everglades.

As you traverse through swamps and marshes, you might even encounter the state’s terrifying yet majestic alligators.

Orlando Airboat Tours is ready to give you an amazing tour, so stop by the location on Nepture Road.

Shop with Style at The Loop

The Loop is an outdoor shopping center with a wide selection of shops and restaurants.

Situated at the corner of John Young Parkway and Osceola Parkway, The Loop is divided into two sections: Loop East and Loop West.

Both sections feature a plethora of stores, from well-known international brands to independent shops.

There are also many restaurants, cafes, and eateries to choose from if you want to grab some grub.

The best thing about this place is that it’s clean, well-maintained, and really spacious.

If you’re looking to go for a relaxing shopping experience, stop by The Loop.

Have Family-Friendly Fun at Old Town

Entryway of Old Town Kissimmee


Looking to have fun with the whole gang?

Old Town is the perfect place to experience the best family-friendly attractions in the city of Kissimmee.

Located on West Irlo Bronson Memorial Highway, Old Town features 70 unique shops, restaurants, and attractions in an 18-acre space.

It focuses on providing visitors with a classic Florida experience with their simple yet timeless rides like the carousel and Ferris wheel.

The famous carousel at Old Town Kissimmee

Mena Correia /

It also has other fun attractions like a shooting alley, a magic hall, and an obstacle course.

The park also has a great selection of restaurants and bars selling classic American comfort foods and beverages.

If you’re looking for souvenirs, the park has gift shops and stores selling unique items like handcrafted art, funny toys, and more!

Buildings along Old Town Kissimmee

Timothy OLeary /

Go Ice Skating at The Ice Factory of Central Florida

If you’re looking to try out ice skating, you need to visit The Ice Factory of Central Florida.

Located on Partin Settlement Road, The Ice Factory of Central Florida is Kissimmee’s premier destination for some fun skating sessions on ice.

It features two amazing ice rinks: the NHL Regulation Ice Sheet and the Studio Ice Sheet.

Like most people, you should try out ice skating at the Studio Ice Sheet.

It has an area of 85 feet by 45 feet, the perfect size for those looking for some simple recreational skating.

Experience the joy of skating on ice at The Ice Factory of Central Florida.

Race with Go-Karts at Kissimmee Go-Karts

The family-friendly fun continues at Kissimmee Go-Karts.

Kissimmee Go-Karts has been providing the city with the best Go-Kart experience for over 20 years.

It features a track that is almost 1 mile long, the largest in Central Florida.

You’ll get to race with your friends on this amazing track with their state-of-the-art single and double-seater Go-Karts.

Aside from that, they also have two other attractions: the Gator Pool and Arcade.

The Gator Pool lets you meet with a real Florida alligator, where you’ll get the opportunity to feed the mighty beast.

The arcade is also amazing as it features over 50 classic arcade games like Pac-Man and Galaga.

Have a need for speed?

Head to Kissimmee Go-Karts located on West Irlo Bronson Memorial Highway.

Play Golf in Rainforests and Caves at Congo River Golf

Congo River Golf is an award-winning miniature golf course with African-themed attractions.

Located on West Irlo Bronson Memorial Highway, Congo River Golf offers a unique challenge to miniature golf enthusiasts.

As you play a game of miniature golf, you’ll get to traverse tropical rainforests, mysterious caves, and majestic waterfalls.

But golf isn’t the only thing that’ll entertain you in Congo River Golf.

The establishment offers other fun activities like gator feeding, scavenger hunts, and an arcade.

Experience an unforgettable African adventure at Congo River Golf!

Other Things to Do Nearby

Enter the Magical World of Disney at Walt Disney World Resort

Road entrance of Walt Disney World Resort


Walt Disney World Resort in Orlando is arguably the most famous attraction in Florida.

It’s not surprising as Walt Disney World Resort lets you enter the magical world of Disney.

It is made up of 4 amazing parks with different themes and attractions.

Animal kingdom at Walt Disney World Resort

JHVEPhoto /

Meet some of your favorite Disney characters like Mickey Mouse, Donald Duck, and more!

The park also has a wide selection of shops and restaurants that offer amazing Disney-themed snacks and meals.

You can get to Walt Disney World Resort via West Osceola Parkway in Orlando, Florida.

Walt Disney and Mickey Mouse statue at Walt Disney World Resort

Anna, CC BY-SA 4.0, via Wikimedia Commons

Discover the Sweet World of the Chocolate Museum & Cafe

Chocolate Museum & Cafe is another one of Florida’s quirky and distinctive establishments.

Located on International Drive, Chocolate Museum & Cafe offers a variety of chocolate-themed desserts, pastries, and beverages!

You should definitely try out their house specialties, including the chocolate fondue, quiche sampler, and cheese platter.

They also have savory dishes like paninis, salads, and caffeinated beverages to balance out the sweetness of the chocolate.

What’s unique about this place is the chocolate museum showcasing the cacao fruit, a tropical fruit which chocolate came from.

Prepare to Be Wet at SeaWorld Orlando

Welcome sign of SeaWorld Orlando


SeaWorld Orlando is another well-known attraction in Florida.

Unlike the previous entry, SeaWorld Orlando offers visitors an exciting and fun aquatic adventure.

Killer whale at SeaWorld Orlando

dmitro2009 /

The park has the usual rides and attractions like roller coasters, drop towers, and carousels.

However, you have to try out their exhilarating aquatic rides like the Manta, Infinity Falls, and Journey to Atlantis.

It also hosts educational tours where you’ll get to meet the cutest creatures in the 7 seven seas, such as penguins, dolphins, walruses, and belugas.

Rollercoaster at SeaWorld Orlando


Their live shows features these cute animals, as well as other themed shows like the Sesame Street Halloween Parade.

Come and experience the most awesome adventure in SeaWorld Orlando on Sea World Drive.

Dolphins at SeaWorld Orlando

Benny Marty /

Final Thoughts

Kissimmee is a vibrant and wonderful city filled with all sorts of unique and quirky establishments you can’t find anywhere else.

The people have a deep appreciation in their rich history and celebrate their wonderful culture.

It’s also a premier destination for outdoor enthusiasts who crave adventure.

The nearby cities, especially Orlando, also offer an amazing experience with their abundance of theme parks.

Because of these things, you should definitely check out the 15 best things to do in Kissimmee, Florida.

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