48 Hours in Kissimmee, Florida: The Perfect Weekend Itinerary

Kissimmee, also known as the Gateway to the Everglades, is situated in Central Florida, just south of Orlando, and is considered a part of the greater Orlando area due to its location. It was originally a cattle ranching town during the 1800s and played an important role in Florida’s cowboy culture. However, today it is one of the most famous tourist spots in the United States of America and is known for its famous attractions, historical locations, dining culture, vibrant nightlife, diverse culture, and more.

From the vintage atmosphere and classical car vibes of Old Town to the reptile encounter and wild experiences in Gatorland, Kissimmee is a place that combines adventure, history, and nature into one remarkable experience. Visit the military museum to travel back in time, relax at the Kissimmee Lakefront Park with stunning views of the lake, or take a trip to the Kennedy Space Center to gain information about the space history of the city. Not to forget, Kissimmee features a delicious food scene that draws inspiration from local flavors and cuisine from all around the world, providing you with a mouthwatering experience.

Planning to visit Kissimmee for 48 hours? Don’t worry, we have got you covered. Below is the list of the ultimate 48-hour guide, including famous Kissimmee attractions, breakfast, lunch, and dinner places, nature landmarks, museums, and theme parks. Keep reading to find out more!

Start your first day in Kissimmee with breakfast at Cracker Barrel Old Country Store, serving authentic, comforting Southern flavors in a cozy and home-like atmosphere. The menu consists of all-day breakfast favorites and includes options like fluffy buttermilk pancakes, country-fried steak with eggs, hearty omelets, and biscuits. Families can also share generous meal baskets, such as home-style chicken and French toast. You can also savor sides like loaded hash brown casserole, fried apples, crisply fried casserole tots, and fried apples to enhance the experience. Don’t forget to pair your meal with their drink options like peach tea, sweet or unsweet iced tea, and freshly brewed premium coffee for a satisfying start to your busy morning.

After having breakfast, visit the Old Town, which is a walkable district styled like a Florida Main Street and is situated along Highway 192. It is home to more than 70 quirky shops that sell souvenirs, retro candies, and local finds, as well as a wide range of restaurants that keep everyone filled. You can also ride on the Old Town Trolley to explore the area from a new perspective. After that, go to the amusement area situated next to the entrance, where traditional carnival rides spin all day. Ride the high-speed attractions like the SlingShot, great for thrill-seekers, and the 85-foot Ferris wheel, which offers beautiful views of the Kissimmee landscape. If you have kids, visit the South Plaza, which is home to kid-friendly attractions like Fun Rides and a carved carousel from 1912.

After exploring Old Town, continue your morning at the Boggy Creek Airboat Adventures, which offers a genuine Florida wildlife experience. Here you will be able to ride a high-speed airboat that travels across a natural wetland with a captain authorized by the U.S. Coast Guard who will show you a wide range of turtles, wading birds, and alligators in their natural home. The boat is open-air and provides clear views of the wildlife, so make sure to bring your camera. After the ride, take a walk along the lakeside walkways to observe the gator pond, visit the butterfly garden, which is home to native butterfly species, or engage in gem and fossil mining. It’s an enjoyable and simple way to get a close-up look at Florida’s wildlife.

Visit the Black Angus Steakhouse and Saloon situated in the center of Kissimmee for lunch. It is a laid-back restaurant that is renowned for its hand-cut USDA Choice and Certified Angus Beef steaks that are grilled fresh every day. In addition to steaks, the menu also offers pizza, chicken sandwiches, substantial pasta meals, salads, and steak burgers. If you are a seafood lover, you can try their freshly prepared fish, salmon, shrimp, or lobster tails. Or if you are feeling adventurous, don’t forget to try their alligator appetizers. The restaurant features a full bar, homemade soup, and a family-friendly atmosphere, making it a great place to have traditional Florida lunch.

Once you are done with lunch, take a trip to the Osceola County Welcome Center and History Museum to learn about how Kissimmee evolved from early Native American trading areas. Here you can explore life-size nature dioramas with interactive exhibitions and scavenger hunts that depict local habitats such as Lake Coastline, pine flatwoods, oak hammocks, and swamplands. You can also visit the Pioneer Village, which is home to historic structures like the Ross Lanier House, a blacksmith house, a schoolhouse from the 1880s, and a citrus packing house. The museum also has a screened-in room that features views of the Shingle Creek situated on the 7.8-acre Mary Kendall Steffee Nature Preserve. Here you can enjoy the serene views of the stream and the surroundings without worrying about insects.

End your afternoon with a visit to the Museum of Military History in Kissimmee, which is a veteran-owned museum honoring those who served. The exhibitions here cover important conflicts from the Civil War and World Wars to Vietnam and contemporary operations and feature real uniforms, weapons, medals, and personal stories. Visit the replica of the Florida Vietnam Wall, which is home to the names of 1,952 Floridians who never returned. Moreover, visitors can also view military vehicles and participate in interactive activities like a helicopter simulator. The educational displays make history simple to understand and show the true cost of freedom and service to visitors of all ages.

Visit the Texas Roadhouse, which is a family-friendly restaurant renowned for its hand-cut steaks, fall-off-the-bone ribs, and substantial sides, providing a great end to your day. Start your meal with appetizers like cactus blossoms, rattlesnake bites, potato skins, or fried pickles. After that, indulge in main course dishes like Dallas Filet, USDA Choice sirloin, New York Strip, Ft. Worth ribeye, as well as pairings like grilled shrimp or ribs with sirloin. The menu also features delicious desserts like strawberry cheesecake or Granny’s Apple Classic to satisfy your sweet tooth. The restaurant features a lively setting with live music and a jukebox, freshly baked bread, and refreshing drinks, making your dinner a memorable one!

Cap off your first night in Kissimmee by visiting Sun on the Beach, which is a bustling bar with a beach motif and is situated in the entertainment district of Old Town. It features Florida Keys vibes inland with its tropical décor, big stage, dance floor, and four bars. Visitors can take in the live music and exciting shows while sipping trademark drinks like Mai Tai, Mermaid Water, and Island Blue Margarita. The bar also features themed nights on the weekends. After enjoying, take the 64-oz Fish Bowl as a memento to take home, or relax outdoors while taking in the festive atmosphere. It’s a great place for an exciting and unforgettable night.

Start your second day in Kissimmee by having breakfast at the Maple Street Biscuit Company. It is well known for its flaky and buttery biscuits and serves a wide range of both sweet and savory options for breakfast, like traditional eggs and cheese sandwiches, fried chicken and bacon dishes, breakfast bowls, waffles, as well as several Southern-style sides to go with your meal. The café also offers craft coffee, which is roasted by Muletown Coffee Roaster. It is open daily and combines comfort food with a modern twist, making it one of the best Places to visit in Kissimmee for breakfast.

After breakfast, go on your amazing adventure by taking a morning trip from Kissimmee to the Kennedy Space Center Visitor Complex situated on Merritt Island. Here, visitors can participate in the Astronaut Training Experience, enjoy the Shuttle Launch Experience by boarding the famous Space Shuttle Atlantis, and meet actual astronauts. You can explore the Apollo/Saturn V Center’s historic spacecraft, take a walk in the Rocket Garden, or explore interactive exhibitions like Journey to Mars. The complex also features several daily astronaut presentations, IMAX movies, and hands-on activities, making it one of the best things to do in Kissimmee for a morning trip.

If you have time, visit the nearby attractions like the Air Force Space and Missile Museum. It was established in the 1960s and features rockets, satellites, missiles, and historical displays that highlight the history of rocket and space flight. You can also visit the Golf N Gator to enjoy a mini-golf session in the morning. It is home to 18-hole courses, Swamp Cave, and Gator Mountain, and allows visitors to enjoy lush vegetation, waterfalls, and ponds that are teeming with fish and turtles. Or if you are a craft beer enthusiast, visit the Florida Beer Company close to Kennedy Space Center and sample their newest brews while taking in live music.

Have your lunch at the El Tenampa Mexican Restaurant, which is a lively cantina with vibrant murals and a genuine Mexican atmosphere. It is an ideal place to have a delicious Mexican lunch where visitors can savor dishes like tacos, enchiladas, and chicken fajitas, as well as vegetarian-friendly selections including guacamole, vegetable fajitas, and quesadillas. Every dish is enhanced by fresh sides like beans, tortillas, cheese, and pico de gallo. It is a great option for recharging and enjoying a filling lunch before going on your afternoon exploration.

Spend your afternoon visiting the Gatorland, which is the first theme park in Kissimmee and covers an area of 110 acres. It is also called the alligator capital of the world and is home to thousands of alligators, rare white gators, and exotic birds. Take in exciting activities like the Stompin’ Gator off-road adventure through an actual Florida wetland, or go on the Screamin’ Gator Zip Line, which allows you to fly over live alligators at 35 to 40 mph. You can also hand-feed alligators during the adventure hours or enjoy fun shows like Gator Jumparoo and close-up reptile encounters. Gatorland is also home to the Splash Park, petting zoo, and aviary, making it one of the best places to visit in Kissimmee for people of all ages.

If you want to spend your afternoon in a more relaxed way, then visit the Kissimmee Lakefront Park, which is situated between Lake Tohopekaliga and Downtown Kissimmee. Here you can enjoy birdwatching with egrets, Sandhill cranes, and occasional bald eagles, stroll along the lakeside walks to see fish and turtles, or unwind under oak trees on Veterans Lawn. The park is also home to several attractions like the Monument of States, the lighthouse, and Veterans’ Islands. You can also rent a paddleboard or kayak from Big Toho Marina and enjoy a peaceful ride on the water, admiring the nearby scenery. The park is also home to several playgrounds, pavilions, and a fishing pier, making it ideal for families.

Spend your evening in Kissimmee by visiting Medieval Times, which is a dinner theater that brings the 11th century to life. Visitors here may witness knights participating in sword fights, jousting, and skills games on powerful horses while cheering for their champion. It is situated close to the center of Kissimmee and allows visitors to see breathtaking horsemanship, falconry, and medieval combat for 2 hours. Visitors of all ages may experience the energy and excitement of a live medieval tournament in this family-friendly event that combines history with skill and entertainment.

During the show, you can also enjoy a four-course medieval meal that features garlic bread, roasted chicken, sweet corn, tomato bisque, herb-basted potatoes, and a dessert that is served with coffee. There are also gluten-free, vegetarian, and vegan options available for visitors. The meal combines grilling dishes with engaging entertainment, and eating it with your hands is required, as it is a medieval custom.

Turn your Kissimmee getaway into a stress-free experience by staying at Rodeway Inn Maingate — close to the fun, easy on your budget, and perfect for a quick Florida escape. Book your stay now: