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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21 - 30 of 37 results

21 - 30 of 37 results

Wooden boardwalk winding through a peaceful cypress swamp surrounded by tall trees at Gatorland near Kissimmee, Florida.

Explore the natural side of Gatorland along its scenic boardwalk, where towering cypress trees and still waters showcase the beauty of Florida’s wetlands.
Itinerary

Influencer Itinerary: 4 Days of Outdoor Adventure & Indoor Leisure

Discover how Florida Instagrammer Angela Jones and her husband, Matthew Lewis, embraced the best of Kissimmee—from serene vacation-home downtime to standout moments in nature, dining, and after-dark fun. Their trip showcases just how effortlessly a Kissimmee getaway can balance relaxation with adventure.
Two people lounging by the pool at the Gaylord Palms Resort and Convention Center enjoying drinks and food.

Enjoying drinks and food poolside at the Gaylord Palms Resort and Convention Center
Itinerary

A Three-Day Itinerary for a Quiet Getaway

There’s a quieter stretch on the Kissimmee calendar when the pace softens, the weather cooperates, and the destination feels refreshingly open. Fewer crowds, easier reservations, and more room to enjoy familiar favorites make this an ideal time for a long weekend or spontaneous escape. This three-day itinerary highlights how Kissimmee shines when timing does the work, and everything feels just a little easier.