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.

0

1 - 10 of 34 results

1 - 10 of 34 results

Corporate Meetings and other Special Event Services

Kissimmee's grandest home rentals are event-ready spaces that easily accommodate special occasions and corporate gatherings.

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 young children sit outside on bright turquoise chairs, enjoying ice cream at a table in front of a shop in Downtown St. Cloud, Florida. One child licks a waffle cone while the other eats with a spoon. — Sweet moments outside Pops Waffle & Ice Cream Shoppe in Downtown St. Cloud, where every cone comes with a smile.

Best Sweet Treats in Downtown St. Cloud

Craving something sweet? Discover the best dessert spots in Downtown St. Cloud, Florida, from colorful snowballs and waffle sundaes to chocolate-covered strawberries and more family-friendly treats.

Two young children sit outside on bright turquoise chairs, enjoying ice cream at a table in front of a shop in Downtown St. Cloud, Florida. One child licks a waffle cone while the other eats with a spoon. — Sweet moments outside Pops Waffle & Ice Cream Shoppe in Downtown St. Cloud, where every cone comes with a smile.

Top Dessert Spots in Downtown St. Cloud

From ice cream to chocolate-covered strawberries, find your next favorite sweet treat at a local bakery or dessert shop.

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.

Two drinks in plastic cups are on a white table with a greenery background. The ube drink on the left is light purple with darker purple swirls and is topped with a glazed ube doughtnut and white icing. The peanut butter drink on the right is light brown with chocolate swirls and is topped with a glazed doughnut covered with crumbled peanut butter cups and a straw. — Ube and peanut butter cup beverages at Everglazed Donuts and Cold Brew.

Everglazed Donuts and Cold Brew in Kissimmee for the Perfect Sweet and Bold Experience

Indulge in the perfect combination of fresh doughnuts and smooth cold brew at Everglazed Donuts and Cold Brew in Disney Springs. Enjoy unique flavors, local ingredients, and an unforgettable experience.

A father and daughter smile and point at assorted chocolates and sweets inside a glass display case at a candy shop. — A sweet decision unfolds as a father and daughter choose their treats together at a classic candy counter.

Where to Find the Best Ice Cream and Frozen Treats in Kissimmee

There’s no sweeter way to cool off from Florida’s sunshine than with a scoop of ice cream or a frosty dessert. Here are six must-try spots for frozen treats in and around Kissimmee.

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

Written by the