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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 35 results
1 - 10 of 35 results
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A Family Road Trip to Kissimmee
Join Dr. Laura Scott and her family on a road trip to Kissimmee, Florida, where family fun meets relaxation, local flavor, and the kind of sunshine that makes every moment brighter.
Catch a car show at Old Town Kissimmee
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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.
Rolling into Old Town style, where classic cars and classic Florida fun cruise side by side.
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Top Car Shows and Automotive Experiences in Kissimmee
Kissimmee is a dream destination for car lovers. From weekly meetups and classic-car cruises to world-famous auctions and auto attractions, the area is full of experiences that get engines — and enthusiasts — fired up.
When your vacation home feels like a private resort, relaxing becomes your easiest daily ritual.
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Save vs. Splurge Experiences
Whether you tend to save or splurge when on vacation, Kissimmee, Florida, has amazing experiences for every budget.
Cannonballs, sunshine, and your own private pool. This is vacation freedom, Kissimmee-style.
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Your Guide to Hosting the Ultimate Florida Pool Party
Take a dip with your closest friends in an awesome Kissimmee pool. Before splish-splashing the day away, here are a few tips for hosting an unforgettable pool party when you’re vacationing in the Sunshine State.
Make this roadtrip your family's favorite / Getty Images
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Kissimmee Road Trip Bingo
Our Kissimmee Bingo cards highlight local wildlife, signs, and transportation, and are sure to make your road trip to Central Florida just as fun as the destination itself is.
Mardi Gras magic comes to life in a swirl of color, music, and high-energy celebration.
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How to Celebrate Carnival in Osceola County
Explore some of Florida's best eateries during Carnival! Explore Downtown St. Cloud and Kissimmee's top restaurants for a festive and flavorful experience.
Take your kids on the Ferris wheel at Old Town Entertainment District
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Free Things to Do in Kissimmee
Looking for affordable fun in Central Florida? From outdoor adventures to cultural treasures, discover free things to do in Kissimmee beyond the theme parks.
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