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A Few Ideas for Your Military Reunion in Kissimmee

Experience Kissimmee has created several sample itineraries that include a variety of tour options your military reunion members will enjoy. Featuring some of our most popular attractions—as well as discoveries off-the-beaten-path—these itineraries are just a small taste of all the activities you can do during your military reunion in Kissimmee, Florida!

Call our Military Reunion Specialist at 407-569-4800 or email us today for your perfect custom one-, two-, or three-day itinerary.


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Tour #1 – Kissimmee’s Tour of Duty

(Allow a minimum 4.5 hours)

Kissimmee’s Tour of Duty itinerary starts at the Museum of Military History, where your reunion group can learn about America’s military through hands-on exhibits. Then it’s off to Warbird Adventures & Stallion 51 for a unique look at vintage aircrafts restoration projects and the impact Kissimmee had on training fighter pilots during WWII.

Round out the tour with a stroll through Celebration Town Center. Enjoy unique shops, a veritable buffet of dining options, or just sit back and enjoy the lakeside.

Tour #2 – A Sweet Journey Back in Time

(Allow a minimum 3 hours)

Start your afternoon with a trip to Old Town Kissimmee for a unique collection of specialty shops, restaurants, and activities. Every Saturday night is the iconic Classic Car Cruise where owners from around the state gather to display their customized autos. Enjoy the festive atmosphere filled with live music.

Your tour would not be complete without a trip to Chocolate Kingdom. A guided tour reveals the transformation process from cacao bean to creamy chocolate. Create your own chocolate bar, ready in just 10 minutes! Then visit the museum and chocolate retail store. (A chocolate memento with US Military branch insignia may be provided at the end of the tour.)

Tour #3 – Fantasy of Flight

(Allow a minimum 3 hours)

With more than 100 of aviation’s greatest accomplishments on display, Fantasy of Flight houses the world’s largest private collection of vintage aircraft. See airplanes from WWI, the Golden Age of Flying, WWII, and post-WWII. Plus, go on the ultimate flying adventure in a Boeing Stearman PT-17, where you take the controls on a 30-minute flight experience.

Visit the Immersion Environments, where life-size exhibits will have you trekking through snow-covered trenches in France during WWI, riding in the belly of a WWII B-17 Flying Fortress on a bombing mission, and soaring to new heights in their hot-air balloon and hang-gliding simulators. Take a trip down memory lane at the Officers Club.

The Legends & Legacies series offers rare opportunities to meet real heroes such as Tuskegee Airmen, historians revealing the secrets of espionage during the Cold War, or first-hand accounts of bravery during modern-day conflicts. You can also host a dinner for your group.

Tour #4 – Burps and Bites

(Allow a minimum 3 hours)

Kissimmee is home to the Tupperware World Headquarters Museum, better known as the Confidence Center. Showcased is the history and legacy of Tupperware through touch-screen kiosks displaying videos and product ranges as well as interactive quizzes, making the experience fun and informative. See how product designs have evolved throughout the years and shop in the gift store.

Just north of the Confidence Center is Gatorland where you can interact with gators and see rare white ones. The free-flight aviary, petting zoo, one-of-a-kind animal shows, and natural alligator breeding marsh ensure your day will be filled with fun, smiles, and special memories! (Don't forget to pick up some gator bites to take home.)

Tour #5 – Heritage Trail

(Allow a minimum 3 hours)

Get ready to go back in time to the pioneer days. The journey starts at the Osceola County Welcome Center and History Museum, home to four different multi-sensory exhibits including swampland, pine flat woods, oak hammock, and lakefront, as well as exhibits showcasing how the early shipping industry, cattle ranching, agriculture and Civil War shaped our county.

Your next stop is Spence Lanier Pioneer Center, where you can stroll through a collection of historic buildings. Experience what it was like to live in an authentic 1898 “Cracker House”, shop for your provisions in a 1900 general store, and work in a blacksmith shop and sugar cane mill. Take in the beauty and nature at Steffee Landing where a historical cabin from the 1880s sits on the slow-flowing waters of Shingle Creek.

If time allows, you can take a canoe or kayak trip down Shingle Creek or meander down the 1.5-mile trail under the pines and scrub oaks.

Tour #6 - Experience Kissimmee and More

(Allow a minimum 3 hours)

The Kissimmee historic downtown area is steeped in history built on steam boats, sugar, cattle, and oranges. Start out at the Welcome Station for maps, information, crafts by local artists, and specials on downtown shops and restaurants. Some sites not to miss are The War Veterans Monument, the Bataan-Corregidor Memorial statue dedicated to Americans and Filipinos who fought in the Philippines during WWII.

The beautiful historic Osceola County Courthouse is the state’s oldest courthouse in continuous operation since it opened in 1890. Nearby in downtown St. Cloud, a city settled by veterans of the Civil War, is History Museum built in 1914 by Union Veterans and contains many original items, as well as Civil War memorabilia.

Are you looking to turn the excitement up a notch? Airboat Rides are a great way to do just that and see the wilder side of Central Florida. Whether you choose to go fast or slow, with so much wild life calling Kissimmee home, you are bound to see gators, bald eagles, and more.