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 19 results

1 - 10 of 19 results

Central Florida Beer Guide: Lager Than Life Local Brews

Discover the best local breweries and beer experiences in Central Florida. Explore Kissimmee’s top spots for craft brews, taprooms, and unique beer-inspired fun on your next getaway.

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 bartender pours a beer at Celebration Brewing Co. — Enjoy a crisp beer at Celebration Brewing Co. in Celebration, Florida.

Local Spots in Downtown Kissimmee & St. Cloud

Explore downtown Kissimmee and St. Cloud for local boutiques, elevated bars, and entertaining nightlife in Central Florida.

Red mocktail in a nest-like arrangement from the ette hotel.

Explore Kissimmee’s Best Zero-Proof Drinks and Alcohol-Free Experiences

Discover refreshing zero-proof drinks and alcohol-free experiences throughout Kissimmee’s vibrant culinary and entertainment scene. From handcrafted mocktails to family-friendly hangouts, you’ll find plenty of flavorful ways to sip, savor, and celebrate. No alcohol required.

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.

ICEBAR Orlando: Unique Nightlife Experience

At ICEBAR Orlando, discover a winter wonderland in Florida, complete with ice sculptures, ice furniture, and ice cocktail glasses.

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.

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.

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.

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.