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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91 - 100 of 166 results

91 - 100 of 166 results

Entrance to Orlando Vineland Premium Outlets

Complete Guide to Orlando Vineland Premium Outlets

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Nighttime scene at Old Town Kissimmee featuring classic cars cruising down the brick streets, colorful shops, and visitors enjoying the lively atmosphere. — Experience the charm of Old Town Entertainment District, where classic car shows, family fun, and vintage vibes light up the night.

Old Town Entertainment District: Timeless Fun

In Kissimmee's Old Town Entertainment District, every day (and night) is a throwback — complete with car shows, a classic Ferris wheel, and live music.

A father and son fishing in Central Florida.

Fishing for the Big Catch in Kissimmee

Kissimmee's local fishing spots offer a break from the hustle and bustle of Central Florida.

A couple walks hand in hand along the dock outside The BOATHOUSE at Disney Springs, smiling under a bright, partly cloudy sky with the restaurant’s tower and outdoor umbrellas in the background. — Strolling into golden-hour bliss at The BOATHOUSE in Disney Springs, where waterfront dining and warm-weather daydreams pair perfectly.

Valentine's Day Guide to Kissimmee

Whether you’re longtime romantic partners or a new couple looking for a fun, memorable day, Kissimmee is the perfect place to spend the day with your Valentine.

Families enjoying outdoor entertainment at Promenade at Sunset Walk in Kissimmee, Florida, with a woman and young girl hula-hooping under palm trees on a sunny afternoon. — Fun and sunshine go hand in hand at Promenade at Sunset Walk in Kissimmee, where live entertainment, dining, and family-friendly vibes create the perfect Florida day out.

Top Things to Do at Promenade at Sunset Walk

Welcome to the Promenade at Sunset Walk in Kissimmee, Florida. This hub for family fun and entertainment is just minutes away from world-famous theme parks and offers an array of exciting experiences for everyone in the family.

Wild Florida Drive Through Safari

Wild Florida Adventure Park: Wildlife Adventures

Ride an airboat, stroll around to see animals, or take a drive through the Safari Park at this outdoor treasure in Central Florida

Albino alligator at Wild Florida.

How Albino Alligators Thrive in Colder Weather

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Two children dressed in Halloween costumes pose playfully with a LEGO® mummy character during Brick-or-Treat at LEGOLAND® Florida Resort. — Spooky fun for the whole family! Kids can show off their costumes alongside a LEGO® mummy at Brick-or-Treat at LEGOLAND® Florida Resort.

Fall Events, Halloween Fun & Things to Do in Kissimmee

Celebrate the season with unforgettable fall events in Kissimmee, from family-friendly festivals and foodie favorites to haunted houses and Halloween thrills at top theme parks.

A plate of carnitas tostadas garnished with lime, cilantro, and queso fresco at Planet Hollywood in Disney Springs, with the Aerophile balloon visible in the background. — Carnitas Tostadas from Planet Hollywood pair perfectly with sunny skies and vibrant views at Disney Springs.

Vamos! Your 2026 Guide to Hispanic Heritage Month in Kissimmee and Central Florida

Hispanic Heritage Month runs Sept. 15 through Oct. 15, and Osceola County, one of Florida's three Hispanic-majority counties, throws quite the party. From a decades-old lakefront festival to gallery openings and a Central Florida concert calendar packed with Latin Grammy winners, here's where to catch the music, art, and flavor this year.

A smiling adult and child lean over a low wall to gently touch a dolphin during an up-close animal encounter, surrounded by lush greenery. — A moment of pure wonder. When curiosity meets connection, memories make a splash that lasts long after the water settles.

Wonder-Filled Thrills at SeaWorld Orlando

See a world of incredible sea life in Florida from penguins to dolphins, ride riveting roller coasters, dine with the sharks, enjoy live entertainment, and more.