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Two Days in Kissimmee, Florida: A Comprehensive Itinerary

By Nick K, Posted on 19 Feb, 2023 at 11:49 am

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Kissimmee Travel Itinerary

Kissimmee, Florida is a great destination for a two-day vacation. Located just south of Orlando, Kissimmee offers visitors plenty of opportunities to explore the city’s vibrant culture and attractions.From outdoor adventures like airboat tours and zip lining to indoor activities such as shopping at Old Town or visiting the Medieval Times Dinner & Tournament show, there’s something for everyone in Kissimmee.

To help plan your trip, we've put together this comprehensive itinerary that will make sure you get the most out of your time in this Central Florida town!

You'll have plenty to do over two days so pack light but don't forget your camera—you won't want to miss any of these amazing experiences!

Day 1


Start your day off right with a hearty breakfast at The Cracker Barrel Old Country Store. This restaurant features classic Southern cooking and offers an extensive menu featuring favorites such as pancakes, omelets, and biscuits. Try their famous country-fried steak and eggs to get your morning off to a great start!

After breakfast, head to Old Town, a shopping center featuring over 75 specialty stores and restaurants. Take a ride on the Old Town Trolley Tour to get an overview of the area or enjoy some exciting go-kart racing at one of the many tracks in this outdoor complex. You can also browse through shops selling souvenirs and memorabilia or grab a bite to eat at any of the restaurants.

Head to Boggy Creek Airboat Adventures for a thrilling airboat experience. This tour will take you on an exciting ride across the lake, where you'll see alligators and other wildlife native to Florida. Don’t forget to bring your camera—you won’t want to miss the chance to capture some incredible photos!



Have lunch at Black Angus Steakhouse & Saloon, a popular restaurant in the heart of Kissimmee. Enjoy mouthwatering steaks grilled to perfection along with classic sides and drinks like beer, wine or cocktails. You can also try out some local specialties such as alligator bites or deep-

After lunch, take a short drive to the Osceola County Welcome Center and History Museum. This museum features exhibits that showcase the history of Kissimmee, from its earliest days as an Indian trading post to its present status as one of Florida's premier cities. You can also find out more about local culture and attractions in the area.

Finish off the afternoon by heading to the Museum of Military History. Here, you can learn all about the United States’ past wars, from World War II to Vietnam. The museum also features a collection of military vehicles and displays that showcase artifacts and personal stories from those who served in times of conflict. You’ll leave with a greater appreciation for those who have served and the sacrifices they made to protect our freedom.


Hotel Recommendations



After a full day of sightseeing, head to Texas Roadhouse for dinner. This family-friendly restaurant serves up classic steak and rib dishes along with burgers, sandwiches, and salads. If you’re feeling adventurous, try their specialty—the Giant Beef Ribs!

Finally, cap off your day with a movie at Regal The Loop & RPX. This state-of-the-art theater offers the latest blockbusters as well as special screenings for kids and adults alike. So grab some popcorn, relax in one of the comfortable recliners, and enjoy the show!


Day 2


Begin your second day with a delicious breakfast at Sweet Escape Celebration. This café offers an array of sweet treats, from French pastries to homemade scones. Try the signature Dutch Baby Pancake or an omelette with all the fixings. You'll also love the fresh-brewed coffees and teas that are perfect for a leisurely start to your day.

After breakfast, make your way to Walt Disney World Resort and enjoy the incredible attractions. Take a ride on Space Mountain or explore Fantasyland and meet your favorite Disney characters. Make sure to catch the daily parades and fireworks shows for a truly magical experience!

For lunch, have a bite at Flame Tree Barbecue. This open-air restaurant located in Animal Kingdom serves up some of the best barbecue around. Enjoy ribs, pulled pork, and other savory dishes while taking in the sights and sounds of the park.


Holiday Rentals



After lunch, get ready for some serious shopping and entertainment at Disney Springs. From designer boutiques to unique gifts and souvenirs, there's something for everyone here. You can also catch a show or movie at the AMC theatre. Plus, there are plenty of restaurants and cafes to choose from, so you won’t go hungry

To finish off your afternoon, take a hot air balloon ride with Orlando Balloon Rides. Soar over the majestic landscape of central Florida and experience breathtaking views of the area. It’s an unforgettable way to end your visit to Kissimmee!



For dinner, try FishBones. This seafood restaurant offers an extensive selection of dishes made with fresh ingredients. Enjoy a lobster roll, grilled mahi-mahi tacos, or other classic favorites. Afterward, head up to the rooftop bar for handcrafted cocktails and live music!

End your day with a bang and catch the nightly fireworks show at Walt Disney World Resort. From Illuminations to Happily Ever After, each show is more spectacular than the last. It’s sure to be a magical ending to an incredible trip!

As you can see, Kissimmee offers plenty of things to do and see. From exploring the city’s history to taking in the sights of Walt Disney World, you won’t be bored! So book your trip today and get ready for a fun-filled adventure!


Wish you have a great journey!

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About Author

Nick K

Nick K, a travel blogger based in Europe, has been a solo traveler for over 15 years. He always has had his head over the skies and his backpack all over the world. He has traveled to over 30 countries and has penned down his experience with the motto of "on the next destination." He has written over 300+ blog posts written with a combo of videos and photography.