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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11 - 20 of 22 results

11 - 20 of 22 results

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.

Melia — The Wilson at Meliã Orlando Celebration

Savor Kissimmee: Dining Destinations for Meetings and Events

Discover top-tier restaurants in Kissimmee that offer everything from resort luxury and chef-driven cuisine to local hidden gems — all perfect for groups, events, or attendees exploring on their own. With a range of private dining options, semi-private spaces, full buyouts, and outdoor seating, these spots are as flexible as they are flavorful.

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.

Woman relaxing on a massage table wrapped in a white towel, surrounded by soft lighting, flowers, and candles in a tranquil spa setting. — Unwind and recharge with a soothing spa experience in Kissimmee.

Bump Up the Fun with a Blissful Three-Day Babymoon in Kissimmee

Calling all moms-to-be! Plan the ultimate babymoon in Kissimmee with this three-day itinerary filled with relaxation, pampering, and gentle adventures. From spa treatments to scenic nature spots, discover why Kissimmee is the perfect destination for a blissful pre-baby escape.

Outdoor lawn at Gaylord Palms Resort & Convention Center at sunset. — Enjoy the artfully crafted outdoor spaces when you stay at Gaylord Palms Resort

4 Reasons to Meet in Kissimmee - The Big, Bold Heart of Florida

Emily Kinney wears sunglasses and smiles while gently greeting a horse at First Nature Ranch in Kissimmee. — New friends and sunny skies. Emily Kinney gets acquainted with her equine co-star at First Nature Ranch.

Emily Kinney’s Kissimmee Soundtrack

Actress and musician Emily Kinney explores Kissimmee in search of quiet moments, creative sparks, and a little rhythm along the way.

Yvette Young sits outside Bok Tower, preparing some music for her performance inside the historic tower. — Surrounded by nature and inspiration, Yvette Young prepares her notes before stepping inside Bok Tower to make music.

Yvette Young Finds Quiet Wonder in Kissimmee

Musician and artist Yvette Young took a soulful approach to exploring Kissimmee, finding inspiration in the quiet, the magical, and the moments in between.

A family enjoying an outdoor meal together at a restaurant patio, smiling and talking over drinks and plates of food on a sunny day. — Good food, good laughs, and that laid-back Florida patio glow. Moments like this taste even better than the barbecue.

3 Spots with the Best Live Entertainment in Downtown Kissimmee

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Smiling girl in a sun shower with an umbrella. — Don't let a little rain ruin your Kissimmee vacation

6 Fun Vacation Things to do on a Rainy Day in Florida

Even in a downpour, there's family fun to be had in Kissimmee — just don't forget your umbrella!

Father and son at the park.

9 Things to Do with Dad in Kissimmee

Celebrate Father's Day the Kissimmee way!