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 32 results

1 - 10 of 32 results

Red Mustang on display during a car show at Old Town Kissimmee — Catch a car show at Old Town Kissimmee

Car Shows at Old Town Entertainment District

Experience the best Kissimmee car shows at Old Town Entertainment District, where classic cars, hot rods, muscle cars, and vintage vehicles shine every week with free admission — alongside family-friendly attractions, dining, and live music.

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.

A stylish entertainment venue with pool tables, a bowling alley, and large-screen TVs glowing under red and blue lights in Kissimmee, Florida. — Enjoy a night of friendly competition with bowling, billiards, and big-screen entertainment at this vibrant venue in Kissimmee.

Food, Fun & Games at Kings Dining & Entertainment

With good food, creative cocktails, and a range of games with a high-end spin, Kings Dining & Entertainment in Orlando makes for a fun afternoon or night out.

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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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.

A couple enjoys drinks and conversation at a stylish café inside the ette hotel in Kissimmee, Florida, seated together on a modern tan sofa under soft ambient lighting. — Savor the moment in Kissimmee, where cozy cafés and stylish lounges set the scene for unforgettable conversations and connections.

Romance & Adventure: A 4-Day Kissimmee Getaway Itinerary

Discover how to plan a romantic and adventure-filled 4-day getaway in Kissimmee, featuring top date spots, outdoor activities, dining, and must-try attractions across Central Florida.

Aseky Family Images

Spring Break Like a Local Itinerary

If you’ve ever been to Florida (or you’re lucky enough to live here), you know just how beautiful and fun it is in spring — not to mention year-round! Read on to discover memorable local favorites and hidden gems for families.

Two people exploring Shingle Creek on yellow kayaks — Kayaking on Shingle Creek

A Local’s 3-Day Guide to a Romantic Getaway in Kissimmee

Join Orlando local Aliya Burshan as she shares her favorite ways for couples to relax, reconnect, and rediscover the magic of Kissimmee in just three unforgettable days.

A woman enjoys zip-lining over an alligator-filled lagoon surrounded by lush greenery at Gatorland near Kissimmee, Florida. — Soar above it all at Gatorland with the Screamin’ Gator Zip Line, a thrilling way to take in Kissimmee’s wild side from high above the park’s iconic alligator breeding marsh.

Family-Friendly Kissimmee Itinerary

Looking for the perfect family escape without traveling far? Motherhood & Lifestyle Influencer @IzzyRose and her young family discovered just that in Kissimmee, a fun-filled destination right in the center of it all, just two hours from their home in St. Augustine.

A family with young kids goes on an airboat ride in Kissimmee — A family-friendly airboat ride in Kissimmee

Tiny Travelers, Big Adventures: A Four-Day Family Escape to Kissimmee

Looking for a family vacation that keeps every kid smiling and every parent sane? Take inspiration from a recent four-day trip to Kissimmee, where dermatologist and Florida mom Dr. Laura Scott and her crew explored the destination’s most playful parks, attractions, trails, and stays. From outdoor adventures to splash-worthy fun, here’s how families of all sizes can experience Kissimmee at its best.