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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1 - 10 of 12 results

1 - 10 of 12 results

Group of friends celebrating the holidays with sparklers and wine around a festive dinner table decorated with candles and Christmas lights. — Ring in the holidays with good food, bright lights, and even brighter smiles during your stay in Kissimmee.

Host Your Next Meeting in Kissimmee and Experience Holiday Magic

Combine productive meetings with the festive spirit of Central Florida’s top attractions and local holiday events.

Two knights sword-fighting on the backs of horses at Medieval Times Dinner & Tournament — Catch a showtime of Medieval Times Dinner & Tournament

Epic Feasts & Battles at Medieval Times Dinner & Tournament

Step into the castle, feast like royalty, and watch an epic battle of gallant knights and old-world chivalry at Medieval Times Dinner & Tournament.

Couple walks through Universal Orlando Resort, smiling and waving near the iconic globe entrance. — Enjoy a sunny day exploring Universal Orlando Resort, one of the most thrilling and unforgettable attractions near Kissimmee, Florida.

A to Z in Kissimmee

Written by the

Knights in Tunnel

Kissimmee Dinner Show Roundup

Not sure which show is right for your crew? Our dinner show roundup breaks down the experiences, flavors and entertainment waiting behind the curtain, helping you find the perfect night out in Kissimmee.

Three meeting attendees walking in the Gaylord Palms Convention Center — Gaylord Palms Resort & Convention Center

Discover Why Kissimmee Is the Ultimate Destination for Meetings and Conventions

Uncover the charm of Kissimmee with easy access, unique venues, and plenty of opportunities for fun in the sun!

Two people sit cross-legged in a bright, minimalist studio practicing alternate nostril breathing as part of a mindfulness or yoga session. — Focused breathwork can bring clarity, reduce stress, and support mental wellness, making it an ideal activity for attendees seeking balance during a busy event. Photo courtesy of Crow Practice.

Breathe Easy: Wellness Tips and Resources for Impactful Meetings

Discover how intentional breathwork — shared by Kristine Iverson, founder of Crow Practice in Kissimmee — can enhance focus, reduce stress, and bring balance to your next event.

A small group of colleagues sits together outdoors, smiling and reviewing printed materials during an informal meeting. — Ideas flow a little easier when the meeting feels more like a catch-up than a conference.

Luxury in Kissimmee: Elevated Experiences for Meeting Planners and Attendees

Discover Kissimmee’s luxury meeting venues, exclusive VIP experiences, and personalized services that elevate every event into an unforgettable escape.

Group of people enjoying an airboat ride through the headwaters of the Everglades near Kissimmee, Florida, gliding over the water with lush green marshes under a clear blue sky. — Feel the rush of adventure on an airboat tour through Kissimmee’s headwaters of the Everglades.

How Kissimmee Blends Business, Fun, and Fresh Ideas

In Kissimmee, meetings go beyond the agenda with unique activations, outdoor adventures, and purposeful experiences that leave a lasting impression on attendees and the community. As Central Florida’s ultimate bleisure destination, hosting here often means record attendance, with participants eager to come early and stay late.

Group of people sitting, laughing and eating.

Adventure & Impact: Best Team-Building Activities in Kissimmee

Discover unforgettable team-building experiences in Kissimmee — where thrilling adventures, meaningful CSR opportunities, and unforgettable memories strengthen your team and leave a lasting impact.

Chelsea Green dressed as a pirate on stage at Pirates Dinner Adventure in Kissimmee, proudly holding two WWE championship belts. — Chelsea Green trades the ring for the high seas at Pirates Dinner Adventure.

Chelsea Green Unwinds with Pirates, Pints & Purring Cats

Wrestling icon Chelsea Green brings her bold spirit to Kissimmee, where she finds high-flying stunts, self-care, and the perfect balance of fun and chill.