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.

51 - 60 of 73 results

A bald eagle soars low over grassy wetlands, wings spread wide against a backdrop of dense green trees. — A bald eagle sweeps across the wetlands, turning a quiet Kissimmee morning into a front-row wildlife moment.

Top 5 Things You’ll Learn About Florida at Boggy Creek Airboat Adventures

Boggy Creek Airboat Adventures features over 32 acres of nearly pristine Florida nature that includes many unique activities such as a Butterfly Garden, Fossil & Gem Mine, a restaurant, and much more just a short drive from Kissimmee.

two fruity drinks being enjoyed poolside — Enjoy a fruity poolside drink at the Meliã Orlando Celebration

Top 5 Resorts with the Best Pool Bars

Sunny Kissimmee wouldn’t be complete without plenty of pool bar options; here are a few of the most amazing pool bars in the area.

Woman golfer lines up a putt on a sunny day at the Omni Orlando Resort at ChampionsGate in Kissimmee, Florida, with the resort’s luxury hotel visible in the background. — Focus meets finesse at the Omni Orlando Resort at ChampionsGate, where scenic greens and world-class hospitality set the stage for a perfect game.

Fore Incredible Kissimmee Golf Vacation Ideas

Planning a golf getaway in Kissimmee? Here are a few must-tee courses we think are a real hole-in-one.

Two people use binoculars and a camera to observe wildlife beside a lakeside trail in Kissimmee. — Quiet mornings on Kissimmee’s trails offer some of the best views for curious wildlife watchers.

4 Incredible Places to see Wildlife in Kissimmee

Embark on a wild adventure in Kissimmee! From serene waterways to thrilling airboat rides and stargazing in pristine parks, discover five must-visit spots to connect with Florida’s incredible wildlife.

Group of 3 girlfriends walking down the sidewalk in downtown Kissimmee examining their shopping bags — Score the find of a lifetime shopping in Downtown Kissimmee

Celebrate Small Business Saturday: 10 Must-Visit Local Gems in Kissimmee

The holidays are a time for giving, and what better way to spread the cheer than by supporting the local businesses that make Kissimmee truly special?

A person pulls a book out of a shelf. — Discover stories that enhance your Kissimmee adventure

Discover Must-Visit Bookstores in Kissimmee for a Literary Adventure

Enhance your Kissimmee adventure with a literary twist! Discover indie bookstores where stories unlock secret speakeasies, spark community connections, and unleash epic comic book quests.

Fishing on Lake Toho

Best Fishing Spots Across Osceola County

Explore the top fishing spots across Kissimmee and St. Cloud for trophy bass and serene lake views — perfect for anglers of all levels.

Two red helicopters parked on a sunny day at International Heli-Tours in Kissimmee, Florida, ready for scenic flights over Central Florida. — Take to the skies with International Heli-Tours and enjoy a bird’s-eye view of Kissimmee’s top attractions.

Top 10 Things to See on the Orlando Helicopter Adventures Tour

Whether you vacation in Central Florida every year or are planning your first family trip to Kissimmee, a bird’s-eye view of the area with the Orlando Helicopter Adventures Tour is a unique experience to start your vacation off right.

Car driving through a safari-style attraction as longhorn cattle approach the vehicle on a grassy path. — A drive-thru safari where the locals have serious horns and zero fear of photobombs.

Top 10 Things To Do at Wild Florida Adventure Park

Where can you have wind in your hair, thrills with live alligators, and relaxing moments with the whole family? Look no further than Wild Florida Adventure Park!

guy in red shirt on a zip line over Gatorland — Soar over Gatorland on the Screamin’ Gator Zip Line

Top 10 Tips For Visiting Gatorland

Gatorland was the first attraction to make its way to Central Florida, and they continue to add exciting features and events to matter how many times you’ve visited.