Family-Friendly Kissimmee Road Trip Itinerary

Looking to get away while staying close to home? We put together a five-day itinerary based on a real road trip that our friend, Motherhood & Lifestyle Influencer @IzzyRose, took with her young family to Kissimmee earlier this year from St. Augustine, Florida.

A woman biking in nature

Explore nature on two wheels when you rent a bike in Celebration

Between an airboat tour, close-up animal encounters, a day at the water park, and oh-so-much more, it was a perfectly Whelmed vacation for the whole family. And as you can see from her photos, she had a fabulous time! 

Let’s start talking itinerary...

Day 1:

Hit the Road

Pack some healthy snacks and pick a playlist. It’s driving time! Need some awesome tunes to groove to on the road? Check out the Experience Kissimmee Spotify channel with playlists that get you in the Florida sunshine mood and fun all the way here.

Make Yourself at Home

After a long drive, there’s nothing better than kicking back and relaxing in your new home away from home. @IzzyRose and her family stayed at Magic Village Yards, known for its beautiful luxury rental properties that are perfect for relaxing after a long drive.

Did you know that Kissimmee has the largest collection of vacation homes in the world? That’s right, it’s the Vacation Home Capital of the World! Take your pick from condos, pool homes, high-value villas, and single-family abodes to 12-bedroom mansions, perfect for reunions or friends sharing a golf, shopping, or spa weekend. Plus, there are even pet-friendly vacation rentals so every member of the family can join in the fun.

Day 2

Get Wild at Wild Florida

Rise and shine — it’s time to visit the world’s only park that offers a drive-thru safari, a gator park, and an airboat tour all in one place! We’re talking about Wild Florida. Travel deep into the protected swamps, marshes, and rivers that make up the headwaters of the Everglades aboard an airboat. During the tour, you’ll get an in-depth look at the gators, birds, eagles, trees, and plants as you glide through endless miles of beautiful wilderness. See for yourself how good it feels to be in the middle of nowhere and get a glimpse at what Central Florida looked like 1,000 years ago! 

Next, it’s time for your self-guided, drive-thru safari tour! You’ll meet more than 100 exotic animals and native Florida wildlife like white-tailed deer, bison, cracker cows, zebras, watusi, and oryx, just to name a few.

Finally, get hands-on during an unbelievable animal encounter at the Gator Park with your choice of sloths, lemurs, porcupines, or gators. And don’t forget to try their delicious barbeque restaurant — the Chomp House Grill — complete with smoked chicken and flavor-packed pulled pork for when lunchtime hits!

Dinnertime at Disney Springs

After your wildlife adventures at Wild Florida and a leisurely afternoon rest or splash at your vacation home, it’s time to grab a bite. Check out Disney Springs for all kinds of delicious family-friendly dining options, unique shopping, and a taste of Disney magic outside of the parks.

Travel back 200 million years when you dine at T-Rex. Your dinner companions will include squawking pterosaurs, wooly mammoths, a massive undulating octopus, and life-sized animatronic dinosaurs — including a 15-foot-tall T. Rex! With a menu of all-American favorites featuring creative twists, it’s sure to please your whole family —  especially if you’ve got a dino lover in tow!

Or, take a journey into the rainforest. The Rainforest Café, that is! The sights, sounds, and aromas of a rainforest welcome you into this classic family favorite. The special effects, animatronic wildlife, and tasty treats turn dining into a whole new experience. 

Wrap up the evening by doing some shopping at some of Disney Springs’ many shops. Grab some Disney souvenirs all over Disney Springs (from clothes and candy to Christmas decor and much more!). You can also shop for your favorite name-brand stores for clothing and accessories. There’s something for everyone here. @IzzyRose even found some delicious vegan baked goods at Erin McKenna’s Bakery NYC!

Day 3

Make a Splash at Island H2O Live!

Make a splash on the slides of Island H2O Live! Check out the multi-guest racer, hang out in the refreshing lazy river, and watch the live entertainment with DJs who make the whole day feel like a party! The experience is totally interactive and unlike any water park you’ve ever visited. Get ready to customize your experience by selecting music and lighting for a number of attractions using a state-of-the-art wristband system. You’ll also enjoy selfie stations, video booths, and on-ride photos and videos to share on social media. Not only that, but you’ll earn points each time you ride to redeem for food and merchandise in the park.

Enjoy a Feast Fit for Royalty at the Medieval Times Dinner & Tournament

Travel back to the 11th century and embark on an unforgettable journey. At Medieval Times Dinner & Tournament, you’ll enjoy a four-course feast in true medieval, pre-silverware fashion, while six knights joust to victory right before your eyes! Bring your appetite and your enthusiasm; you’re sure to have an incredible experience, just like Izzy Rose and her family, whose contender (the Green Knight) won the whole tournament.

Day 4

Get Up Close at Gatorland

At 110 acres, Gatorland provides affordable-priced family fun. The park is home to thousands of alligators and crocodiles, an aviary, a breeding marsh with an incredible observation tower, a petting zoo, and one-of-a-kind reptilian shows.  

Daredevils will love the Screamin’ Gator Zip Line and the Stompin' Gator Off-Road Adventure, which takes you through Florida wetlands and into a massive pond of alligators. And don’t miss out on Gatorland’s White Gator Swamp. You’ll also spot a handful of albino and leucistic alligators. These beautiful animals are very rare in the wild. That’s because their snow-white skin (caused by a lack of melanin in the case of albinism and loss of pigmentation in the case of leucism) makes blending in with their surroundings a challenge. But here in Kissimmee, we think standing out is a good thing!

Shop ‘til You Drop at Orlando Premium Outlets

Score some incredible deals for the whole family at over 160 stores of luxury designers and name brands at Orlando Premium Outlets. It’s a true shopper’s dream, offering some of the biggest names like Saks OFF Fifth, Neiman Marcus Last Call, and so much more. Expect to save big here — we’re talking 25% to 65% off! Now’s your chance to snag that designer item you’ve been coveting at a fraction of the cost. 

@IzzyRose scored some great deals on pajamas for her kids at Carters while treating herself at one of her favorite stores, All Saints, where she bought a leather jacket for more than 60% off. Start the car, it’s time to go shopping!

Day 5

Celebration Bike Rental

It’s almost time to head home, but not before one last adventure for the whole family. Get your heart pumping and legs moving before you’re back in your car and on the road. It’s time for a fun family bike ride! Pedal down the quaint streets of Celebration – a town famous for its nostalgic hometown flavor and elegance. Discover picturesque neighborhoods with world-class architecture and a vibrant downtown area. And take in the natural wildlife while on scenic winding trails and waterfront pathways.

Time to Head Home

That’s one unforgettable family vacation in the books. But don’t feel sad about leaving, and we’ll always be here to welcome you back with sunny Central Florida skies and endless good times. 

Inspired to start planning? Subscribe to our newsletter for up-to-date info, deals, and vacation ideas. And during your Kissimmee visit, don’t forget to share your vacation memories by using the hashtag #MyKissimmee on social media.