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First Time to Kissimmee Itinerary

First time visiting Kissimmee? We have you covered! When you follow this five-day itinerary, you’ll visit iconic spots and hidden gems. You’ll see Kissimmee from across the water, high in the sky, and everywhere in between! And, most importantly, you’ll have an unforgettable experience that’ll take you into a new world of adventure.

Day 1

Disney Day

It wouldn’t be a trip to Kissimmee without a day at Walt Disney World Resort. So, unleash your inner child and watch as your favorite characters and fairy tales come to life right before your eyes.

Disney's Magic Kingdom Park

Start your vacation off in a big way with a morning spent at Disney’s Magic Kingdom Park! Explore six lands of enchantment, ride some of the most famous attractions on Earth, and snap your photo outside Cinderella Castle. It’s sure to be a morning of joy and happiness where dreams come true.

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Disney's Hollywood Studios

After a morning spent at the Magic Kingdom, it’s time to bring your favorite movies to life at Disney’s Hollywood Studios! Become the size of a toy with Buzz and Woody in Toy Story Land, blast off to a galaxy far, far away at Star Wars: Galaxy’s Edge, or take a trip to another dimension on the Twilight Zone: Tower of Terror.

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Day 2

Delicious Dining

In Kissimmee, there’s no shortage of unique places to fuel your fun. Make each meal today memorable with these delicious dining options.

Kissimmee Diner

When it comes to breakfast, you’re going to want to go with a true classic like the Kissimmee Diner. Southern hospitality is a major priority here, as are big portions! Wondering what to choose from their fantastic menu? We’re huge fans of the Big Raskall Breakfast!

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A plate of BBQ.

Big John's Rockin BBQ

Another local favorite, Big John’s Rockin BBQ will rock your taste buds and leave you ready to roll for the rest of your day. And it’s easy to see why! This Kissimmee staple is all about home-style cooking, barbecue, and fresh sauces made by Big John himself.

Medieval Times Dinner & Tournament

Travel back to the 11th century and watch six knights compete to become champion at the Medieval Times Dinner & Tournament. Enjoy a four-course feast in true medieval fashion with zero silverware while cheering on your knight to victory. The only thing better than a delicious dinner is an exciting show to go along with it!

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Day 3

Outdoor Adventures

It’s time to have some fun in the sun. So grab your sunscreen and get ready for wildlife, hot air balloons, and pirates (oh my!).

Bob's Balloon Rides

You’re up early on day three, but trust us, it’s worth it! Your day begins with an early-morning hot air balloon ride with Bob’s Balloon Rides. As you fly high in the sky, you’ll get a new perspective on the scenery and wildlife that you can only get from above. Be sure to bring your camera along for the ride.

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Next, embrace your wild side by getting face to face with an alligator at Gatorland! This local landmark is home to thousands of alligators and crocodiles, as well as a petting zoo, nature walk, zip line, reptile shows, and more. If you want to see some of Kissimmee’s coolest creatures, this is the place for you.

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Pirates Island Adventure Golf

Enjoy a round of mini-golf like no other at Pirates Island Adventure Golf. Follow in the footsteps of pirates like Blackbeard and Captain Kidd and start at a seaside village before departing along the shores of the Tidal Lagoon. Putt your way through caves in search of hidden treasures and catch all kinds of cool views of Pirate Island. X definitely marks the spot for fun here!

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Day 4

Shopping Spree Day

Every trip must be accompanied by a souvenir! Whether you want to shop in luxury locations or score a great deal, there’s no shortage of retail stores in Kissimmee.

The Florida Mall

The Florida Mall is Central Florida’s largest shopping center, with over 250 retail, entertainment, and dining options. Complete with department stores like Macy’s, JCPenney, and Dillard’s, as well as kid favorites like Build-a-Bear Workshop and Crayola Store, this is a perfect family shopping destination.

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The Mall at Millenia

An unparalleled shopping experience right here in Kissimmee, The Mall at Millenia is home to 150 retail stores and eateries. This mall is a must-visit if you’re looking for luxury brands like Chanel, Tiffany & Co., and Gucci — just to name a few. Experience some retail therapy and pick out a new outfit to commemorate your first time in Kissimmee!

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Orlando Premium Outlets

What’s better than 180 designer and brand name outlet stores? How about everyday savings of 25%-65%? That’s what you’ll find at Orlando Premium Outlets, along with brands like Calvin Klein, Kate Spade, Nike, and more. There’s no time like the present to treat yourself!

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Day 5

Universal Orlando Resort Day

Your last day of vacation is all about becoming the main character in your very own action-adventure story, complete with thrills, chills, and a little bit of wizardry at Universal Orlando Resort.

Universal Studios Florida

Discover jaw-dropping fun at Universal Studios Florida. Dodge legendary villains like Voldemort™ (with a bit of help from Harry Potter™ and his friends, of course) on The Escape from Gringotts™, flee an ancient mummy, or get wild with Woody Woodpecker on his kid-friendly rollercoaster. It’s time to go beyond the screen and jump into the action!

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Universal's Islands of Adventure

Welcome to a world where superheroes, beasts, and magical creatures all walk beside you. At Universal’s Islands of Adventure, explore witchcraft and wizardry on Hagrid’s Magical Creatures Motorbike Adventure™, hide from hungry dinosaurs on Jurassic World VelociCoaster, and team up with a real king on Skull Island: Reign of Kong. Your last day here sure is going to be one to remember!

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