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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Brightine

Everything You Need to Know About Brightline Orlando

Brightline makes it easier than ever to explore Florida with modern, eco-friendly trains connecting top destinations in the state. With convenient service between Orlando and major cities like Miami, West Palm Beach, and Fort Lauderdale, Brightline is a stress-free alternative to driving or flying — perfect for visitors looking to experience more of the Sunshine State.

A performer in a vibrant Mardi Gras costume with purple, green, and gold feathers smiles and dances during a nighttime parade. — Mardi Gras magic comes to life in a swirl of color, music, and high-energy celebration.

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.

A bartender pours a beer at Celebration Brewing Co. — Enjoy a crisp beer at Celebration Brewing Co. in Celebration, Florida.

Sip and Savor: Local Drinks at Local Digs in Downtown Kissimmee

Explore Downtown Kissimmee’s best local bars, from craft cocktails to wine tastings. Discover unique drinks, lively atmospheres, and historic charm in every sip!

Red mocktail in a nest-like arrangement from the ette hotel.

Explore Kissimmee’s Best Zero-Proof Drinks and Alcohol-Free Experiences

Discover refreshing zero-proof drinks and alcohol-free experiences throughout Kissimmee’s vibrant culinary and entertainment scene. From handcrafted mocktails to family-friendly hangouts, you’ll find plenty of flavorful ways to sip, savor, and celebrate. No alcohol required.

Playground at Kissimmee Lakefront Park

Todo lo que puedes hacer en Lakefront Park en Kissimmee

¡Vive la experiencia del Lakefront Park en Kissimmee! Sumérgete en la belleza de Lake Toho mientras disfrutas de pesca, paseos escénicos, y momentos inolvidables en familia. Además, descubre los sabores locales en este pintoresco refugio al aire libre.

Sip, Celebrate & Chill at ICEBAR Orlando

At ICEBAR Orlando, discover a winter wonderland in Florida, complete with ice sculptures, ice furniture, and ice cocktail glasses.

Dr. Laura and her family on an airboat at golden hour

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.

A bright vintage car drives past the colorful Old Town entrance arches in Kissimmee, with the Ferris wheel and visitors in the background. — Rolling into Old Town style, where classic cars and classic Florida fun cruise side by side.

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.

Central Florida Beer Guide: Lager Than Life Local Brews

Discover the best local breweries and beer experiences in Central Florida. Explore Kissimmee’s top spots for craft brews, taprooms, and unique beer-inspired fun on your next getaway.

A large family gathers around the Christmas tree in Kissimmee

Vacation Home for the Holidays

Explore the many vacation home rentals available in Kissimmee to find the perfect spot for you and your entire family to celebrate this holiday season!