20 Best & Fun Things to Do in Kissimmee (FL)

Nestled in the heart of Osceola County, Florida, Kissimmee beckons travelers with its unique blend of Old Florida charm and exhilarating modern attractions. More than just a gateway to world-famous theme parks, this vibrant city boasts a rich history, dating back to its origins as a bustling steamboat port and cattle town in the late 19th century.Â

Once known as “Allendale,” it was renamed Kissimmee City in 1884, a name derived from the Jororo Native American word for “long water,” referring to the Kissimmee River and its surrounding lakes.

Today, with a metropolitan area population approaching 600,000, Kissimmee maintains its distinctive character. You’ll find a captivating atmosphere where moss-draped trees line historic streets, and the echoes of cowboy culture still resonate.Â

From thrilling airboat adventures in the headwaters of the Everglades to strolls through charming downtown, Kissimmee offers an unforgettable experience. This comprehensive guide will help you discover the 20 best and most fun things to do in this special Central Florida destination.

Things to Do in Kissimmee, FL

1. Shingle Creek Regional Park

Immerse yourself in the natural beauty of Florida at Shingle Creek Regional Park, often hailed as the northernmost headwaters of the Everglades. This extensive park system encompasses multiple parcels, offering diverse landscapes and a profound connection to the region’s ecological heart.

The park is a haven for nature lovers, with opportunities for hiking, biking, and wildlife viewing. Paddle along Shingle Creek, a serene waterway winding through cypress forests, where you might spot a variety of birds, turtles, and even alligators. The Osceola County Welcome Center and History Museum, located within the park, provides fascinating insights into the creek’s historical significance.

Consider a guided paddling tour to learn more about the ecosystem. Early mornings offer the best chances for wildlife sightings. The park also has accessible amenities, making it enjoyable for everyone.

Address: 925 S Bass Rd, Kissimmee, FL 34746

2. Old Town

Step back in time at Old Town, an 18-acre outdoor walking district designed to evoke the classic charm of a historic Florida town. This lively entertainment complex is a treasure trove of nostalgic delights, offering a family-friendly atmosphere with something for everyone. From unique shops to classic car cruises, it’s a vibrant step into the past.

Here, you can browse an eclectic mix of souvenir shops, specialty stores, and independent boutiques. Enjoy a delicious meal at one of the many restaurants, or grab a sweet treat from a charming ice cream parlor. The highlight for many is the weekly car shows, featuring dazzling displays of vintage vehicles.

Visit on a Friday or Saturday night for the iconic car cruises, when classic cars rumble down the brick-paved streets. It’s a fantastic photo opportunity and a chance to truly experience the bygone era. Check their schedule for special events and concerts.

Address: 5770 W Irlo Bronson Memorial Hwy, Kissimmee, FL 34746

3. Kissimmee Lakefront Park

Discover an urban oasis at Kissimmee Lakefront Park, a beautifully manicured waterfront space on the northwest shore of Lake Tohopekaliga (often called Lake Toho). This expansive park offers stunning views and a wide array of recreational activities for all ages, making it a favorite spot for locals and visitors alike.

The park features picturesque walking paths, a fishing pier perfect for angling enthusiasts, and ample green space for picnics and relaxation. Children will delight in the expansive splash pad and playground areas, while the civic lawn often hosts community events and concerts.

For a unique experience, consider renting a kayak or paddleboard to explore Lake Toho’s tranquil waters. The best time to visit is during sunset, when the skies over the lake explode with vibrant colors. Don’t forget your camera!

Address: 69 Lakeview Dr, Kissimmee, FL 34741

4. Boggy Creek Airboat Adventures

Embark on an exhilarating journey into the heart of the Central Florida Everglades with Boggy Creek Airboat Adventures. This thrilling experience allows you to glide across the wetlands at high speeds, getting up close and personal with the region’s iconic wildlife.

Their powerful airboats navigate through lush swamps and marshes, providing unparalleled views of alligators in their natural habitat, as well as various bird species and other native creatures. Knowledgeable captains share captivating stories and insights into the ecology of this unique environment.

Opt for the longer tour for a more immersive experience. Reservations are highly recommended, especially during peak season, to secure your spot on this unforgettable adventure.

Address: 2001 E Southport Rd, Kissimmee, FL 34746

5. Museum of Military History

For a poignant and educational experience, visit the Museum of Military History. This small yet impactful museum pays tribute to the brave men and women who have served in the United States Armed Forces, showcasing artifacts and stories from various conflicts.

The museum’s collection includes uniforms, weapons, photographs, and personal memorabilia, offering a chronological journey through American military history. It provides a unique perspective on the sacrifices made and the evolution of warfare.

Allow ample time to read the detailed exhibits and engage with the knowledgeable volunteers, many of whom are veterans themselves. It’s a respectful and insightful stop for history buffs and anyone wishing to honor military service.

Address: 5210 W Irlo Bronson Memorial Hwy, Kissimmee, FL 34746

6. Give Kids The World Village

Experience the magic and heartwarming mission of Give Kids The World Village, a non-profit resort that provides cost-free vacations to children with critical illnesses and their families. While not a typical tourist attraction, it’s a place that embodies the spirit of hope and generosity.

The village features whimsical accommodations, attractions, and entertainment designed to create unforgettable memories for these special families. From a gingerbread house ice cream parlor to a castle of dreams, it’s a truly enchanting place.

While direct public tours are not typically offered due to its private nature for wish families, you can support their incredible work through donations or by volunteering. Learning about their mission adds a profound dimension to understanding Kissimmee’s community spirit.

Address: 210 S Bass Rd, Kissimmee, FL 34746

7. Kissimmee Historic District

Take a leisurely stroll through the Kissimmee Historic District, a sprawling area encompassing nearly 70 acres of commercial, residential, and governmental buildings dating from 1889 to 1940. This district is a testament to Kissimmee’s rich past as a thriving Central Florida hub.

Explore charming streets lined with historic architecture, discovering quaint shops, local eateries, and beautifully preserved residences. The district tells the story of Kissimmee’s evolution from a “Cowtown” with cattle drives down Broadway to the vibrant city it is today.

Look for the informational plaques that detail the history of individual buildings. The First United Methodist Church, built in 1913, is a notable example of Gothic Revival architecture. Consider visiting during one of the annual events or markets held in the downtown area for a lively experience.

8. Osceola County Welcome Center and History Museum

Delve deeper into Kissimmee’s fascinating past at the Osceola County Welcome Center and History Museum. This engaging museum provides a comprehensive overview of the region’s history, from its Native American roots to its development as a modern city.

Exhibits showcase artifacts, photographs, and interactive displays detailing the area’s pioneer days, the significance of the cattle industry, and the impact of tourism. You’ll learn about the Jororo people, the role of steamboats, and the influence of early developers like Hamilton Disston.

This museum is an excellent starting point for understanding the local culture and heritage. It’s particularly insightful for families with children, offering an educational and entertaining experience.

9. Spirit of the Swamp Airboat Tours

For another incredible airboat experience, consider Spirit of the Swamp Airboat Tours. They offer intimate and personalized tours of Central Florida’s swamps and marshes, focusing on providing a comfortable and immersive wildlife encounter.

Their small, private boats with padded seats and shaded covers ensure a relaxing journey away from larger crowds. High-tech headsets allow seamless communication with your guide, ensuring you don’t miss any fascinating facts or wildlife sightings.

Book a 90-minute private tour for the most in-depth exploration. Their focus on smaller groups means a more personalized and less rushed experience, perfect for photographers and avid nature observers.

10. Crosslands Shopping Center

Indulge in some retail therapy at Crosslands Shopping Center, Kissimmee’s newest and most popular destination for shopping and dining. This expansive center offers a wide variety of national retailers and popular restaurants.

You’ll find a diverse selection of stores, from major clothing brands to home goods and sporting equipment. After a successful shopping spree, refuel at one of the many casual and sit-down dining options available.

Crosslands is a great spot for both practical shopping and leisurely Browse. Ample parking makes it a convenient stop for all your retail needs.

11. Lake Toho

Experience the vastness and natural beauty of Lake Tohopekaliga, affectionately known as Lake Toho. This large, shallow lake is a central feature of Kissimmee’s landscape and a popular spot for fishing, boating, and simply enjoying the outdoors.

Lake Toho is renowned for its excellent bass fishing, attracting anglers from all over. Beyond fishing, it’s a fantastic place for recreational boating, jet skiing, and airboat tours that explore its intricate network of waterways and marshlands.

Consider hiring a local fishing guide for the best chance of a trophy catch. There are several public boat ramps and marinas around the lake, providing easy access for those with their own watercraft.

Address: Kissimmee, FL

12. Fun Spot America Kissimmee

For a dose of classic amusement park fun, head to Fun Spot America Kissimmee. This family-owned park offers a refreshing alternative to the larger theme parks, with a focus on affordability and a variety of rides for all ages.

You’ll find exciting roller coasters, thrilling go-karts on multi-level tracks, bumper cars, and a range of carnival-style rides. It’s a place where you can enjoy traditional park attractions without the overwhelming crowds.

Look for their “buy one get one free” deals or multi-day passes for better value. The park often has special events and live entertainment, so check their schedule before you go.

Address: 2850 Florida Plaza Blvd, Kissimmee, FL 34746

13. Kissimmee Prairie Preserve State Park

Escape to a truly wild and breathtaking landscape at Kissimmee Prairie Preserve State Park. Located a bit further afield, this expansive preserve protects the largest remaining tract of Florida dry prairie, offering an unparalleled opportunity to experience Florida’s natural beauty.

The preserve is a haven for rare and endangered species, including the Florida grasshopper sparrow and crested caracara. It’s also recognized as Florida’s first Dark Sky Park, offering incredible stargazing opportunities due to its lack of light pollution.

Consider a guided prairie buggy tour to explore the vast grasslands and spot wildlife. For stargazers, plan an overnight camping trip to witness the Milky Way in all its glory. Reservations for camping are essential.

Address: 33104 NW 192nd Ave, Okeechobee, FL 34972

14. Medieval Times Dinner & Tournament

Step back into the Middle Ages and witness a spectacular show at Medieval Times Dinner & Tournament. This popular dinner attraction transports you to an 11th-century castle, where you’ll feast on a four-course meal while cheering on your knight in shining armor.

The immersive experience features jousting, horsemanship, falconry, and sword fighting, all performed by talented knights and their magnificent horses. It’s an energetic and entertaining show for the whole family.

Make reservations in advance, especially for evening shows. Be prepared to eat with your hands, as is tradition in medieval times!

15. The Colonial Estate

Admire the architectural beauty of the Colonial Estate, also known as the Tucker/Ivey House. This Classic Revival style colonial estate, built around 1915, offers a glimpse into Kissimmee’s early 20th-century elegance.

Originally the residence of a Georgia lumber baron, it later served as the Colonial Inn and Club, a popular tourist hotel in the 1920s and 30s. While it is a private residence, its grandeur can be appreciated from the street, showcasing the historical charm of the area.

Respect the privacy of the residents as this is not a public museum. The best view is from Old Dixie Highway.

Address: 101 Old Dixie Hwy, Kissimmee, FL 34744

16. First United Methodist Church

Discover a piece of Kissimmee’s architectural and spiritual history at the First United Methodist Church. Constructed in 1913, this two-story brick Gothic Revival style building is a beautiful example of early 20th-century church architecture.

The church features stunning stained-glass windows that cast a warm glow on the interior, a grand chapel, and an impressive bell tower. It continues to be an active place of worship for the Methodist congregation.

Visitors are welcome to admire the exterior and, if services are not in progress, perhaps quietly step inside to appreciate the interior architecture. It’s a peaceful and historically significant landmark.

17. Wild Florida Airboats & Gator Park

For a comprehensive wildlife experience, visit Wild Florida Airboats & Gator Park. This attraction combines thrilling airboat rides with a fascinating gator park and even a drive-thru safari.

Beyond the airboat tours, the gator park allows you to see hundreds of alligators and other native and exotic animals in a natural setting. The drive-thru safari offers a unique opportunity to observe diverse wildlife from around the world from the comfort of your vehicle.

Allocate a full day to enjoy all the offerings. Consider purchasing a combo ticket for the best value if you plan to experience multiple attractions. They also offer a delicious BBQ restaurant on-site.

Address: 3301 Lake Cypress Rd, Kenansville, FL 34739

18. Dare 2 Escape – Escape Room Games

Challenge your mind and teamwork skills at Dare 2 Escape – Escape Room Games. This exciting attraction offers immersive and themed escape room experiences, perfect for groups of friends or family.

Work together to solve puzzles, decipher clues, and unlock secrets within a set time limit to “escape” the room. Each room has a unique storyline and set of challenges, providing a fun and engaging mental workout.

Book your preferred room and time slot in advance, especially for larger groups. This is a great activity for a rainy day or an evening out.

19. Vivian’s Spa

Unwind and rejuvenate at Vivian’s Spa, a serene day spa offering a range of treatments minutes from the Disney area. After a day of exploring, this is the perfect place to relax and pamper yourself.

They offer a variety of services, including highly customized massages, authentic European facials, manicures, and pedicures. Their professional and friendly staff are dedicated to providing a blissful experience.

Reservations are essential, as they operate by appointment only and cater to a discerning clientele. Inquire about their spa packages for a comprehensive wellness experience.

20. Clearwater Beach

While not in Kissimmee, a day trip to Clearwater Beach offers a quintessential Florida experience that’s easily accessible. Consistently ranked among the top beaches in the United States, it’s a perfect escape for sun, sand, and turquoise waters.

Enjoy the soft, white sands and calm, clear waters of the Gulf of Mexico. Relax under the sun, swim, or partake in various water sports like parasailing, jet skiing, or paddleboarding. Don’t miss the famous Pier 60 for its nightly sunset celebrations.

The drive is approximately 1.5 to 2 hours, depending on traffic. Plan to leave early to beat the crowds and secure a good parking spot, especially on weekends.

Address: Clearwater Beach, Clearwater, FL

Meet the top attractions in Florida, here is a guide on the top things to do in Lake Mary and things to do in Lake Buena Vista

Conclusion

Kissimmee, Florida, is far more than just a convenient hub for theme park adventures. It’s a destination brimming with its own unique history, natural wonders, and vibrant local culture. From the charming cobblestone streets of Old Town to the thrilling airboat rides through the Everglades headwaters, and from peaceful lakeside parks to engaging historical museums, Kissimmee offers a diverse array of experiences that cater to every traveler.

Whether you’re seeking outdoor adventure, a journey through time, family-friendly entertainment, or simply a tranquil escape, Kissimmee delivers. Its blend of rich heritage, natural beauty, and modern amenities creates an inviting atmosphere that encourages exploration and discovery. So pack your bags, embrace the charm of Osceola County, and create your own unforgettable memories in this truly special Floridian city.