Trip Ideas for Your Kissimmee Vacation

Find inspiration for your trip to Central Florida with articles, lists and itineraries featuring things to do and places to explore.

Located minutes from Orlando, Kissimmee is your gateway to Central Florida’s must-do adventures: thrilling airboat rides, vibrant local festivals, family-friendly theme parks, and all the shopping and dining options you could dream of. The hard part is deciding where to start, but that’s where we come in.

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141 - 150 of 246 results

141 - 150 of 246 results

An acrobat from Cirque du Soleil’s Drawn to Life soars through the air above a group of performers onstage at Disney Springs. — A soaring moment from Cirque du Soleil’s Drawn to Life at Disney Springs.

You Know the Theme Parks — Now Discover Kissimmee’s Artsy, Flavorful, Historic Side

Kissimmee has a creative rhythm all its own, from local theater and vibrant murals to Latin flavors, pioneer history, and lively entertainment districts. Whether you're wandering through historic downtowns, strolling Celebration's lakeside streets, or taking a short drive to Orlando’s museums and Broadway-style shows, this corner of Central Florida is full of unexpected cultural finds, all just minutes from your vacation home base.

A woman walking her small brown dog on a sunny day at Dan Tarrell Memorial Point in St. Cloud, Florida, with trees lining the paved path. — A calm day by the lake with tails wagging and sunshine shining at Lakefront Park.

Your Dog-Friendly Adventure in St. Cloud

Discover the best dog-friendly activities in St. Cloud, Florida! From scenic parks and pet-friendly cafés to off-leash play areas, explore top spots to enjoy with your furry friend.

A couple enjoys a meal at Gaylord Palms

Your Guide to Gluten-Free Dining in Central Florida

From local and regional cuisine to international eats, discover some of the area's top restaurants for delicious, gluten-free dining.

A colorful hot air balloon floats low over a wide green field on a clear morning, with light fog in the distance and trees lining the horizon. — Some mornings lift your spirits — this one lifts you right into the sky.

Your Guide to Outdoor Experiences in Kissimmee

Whether you’re a daredevil or a down-to-earth type, you’ll find your ideal adventure under the Central Florida sun. Go biking, play mini golf, take a hot air balloon ride, come face to face with Florida's wild creatures, and more.

A woman's hand holding a cocktail

Your Happy-Hour Guide: Outdoor Dining in Central Florida

Sip margaritas to craft beer and enjoy savory light bites at these top outdoor spots for happy hour.

Love is what makes the world go round at ICON Park, near Kissimmee, Florida.

The Ultimate Guide to ICON Park

Soar to new heights at ICON Park! Our ultimate guide showcases thrilling attractions, great dining, and must-see experiences, including The Orlando Eye — offering unbeatable views of Orlando’s skyline.

Colorful fireworks burst across a dark night sky, with bright streaks of red, blue, green, and gold radiating outward. — A sky full of fireworks lights up the night, turning the celebration into a sparkling finale of color and energy.

The Best New Year’s Eve Fireworks Shows in Central Florida

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A family is excited about holiday treats. — Enjoy sweet holiday treats at LEGOLAND

Best Places at the Theme Parks and Kissimmee for Holiday Treats

Looking to create special memories this holiday season? We suggest sampling some of the holiday treats at the theme parks and throughout Kissimmee has to offer.

Christmas tree in the Gaylord Palms Resort

Christmas at Gaylord Palms 2025: Rudolph the Red-Nosed Reindeer™ and More Holiday Fun

From Nov. 14, 2025 to Jan. 7, 2026, Christmas at Gaylord Palms transforms the resort into a holiday wonderland featuring Rudolph the Red-Nosed Reindeer™, dazzling lights, and family fun.

Beautifully decorated Christmas tree with red poinsettias, silver and gold ornaments, and twinkling lights inside a festive Kissimmee vacation home dining area. — Celebrate the holidays in style in a Kissimmee vacation home with sparkle, festive décor, and where the warmth of the season fills every room.

Creative Ways to "Wrap" a Vacation for Under the Tree

So you’ve decided to surprise the family with an unforgettable vacation to Kissimmee, Florida. Congratulations on winning the holidays! Your gift is sure to be a hit.