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 25 results

1 - 10 of 25 results

'Twas the Night Before Christmas in Kissimmee

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.

A mother and her young son enjoy a meal together while riding the Brightline train, with sunlight streaming through the window and a scenic view outside. — Enjoy a comfortable ride aboard Brightline, savoring snacks and scenery on the way to Kissimmee.

Getting Around Kissimmee by Train: Brightline, SunRail, and More

Discover how to ride the rails in Kissimmee, from fast and convenient train services like Brightline and SunRail to iconic theme park rides like the Walt Disney World® Monorail. Whether you're traveling around Central Florida or hopping aboard a rail-themed adventure, this guide has your ticket.

A man helps his son pretend to fly in Kissimmee, Florida

How to Survive a Long Flight with Little Kids

Air travel with little ones can be challenging if you're not fully prepared. So, we thought we'd share some tips to help make the journey as much fun as your stay in Kissimmee.

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.

Dog treats. — Woof Gang Pastries specializes in gourmet dog treats for your pup

How To Plan A Paw-Some Vacation in Kissimmee, Florida

We want to make sure that every member of your family has the best time ever while vacationing in Kissimmee. Here are a few things we have to offer our four-legged visitors.

A family arrives at their vacation home — Fun awaits in a Kissimmee Vacation Home

Top Things to Pack for Your Kissimmee Road Trip Vacation

The ultimate packing list for your next road trip to Kissimmee, Florida, includes games, comfort, and more!

A man and child run into the pool — Splash and play all day in Kissimmee

When’s the Best Time to Visit Kissimmee?

Whether it’s a spring break, a summer vacation, a fall road trip, or a winter escape from cold weather, every season in Kissimmee offers opportunities for enjoyment.