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 29 results

1 - 10 of 29 results

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.

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

Local Spots in Downtown Kissimmee & St. Cloud

Explore downtown Kissimmee and St. Cloud for local boutiques, elevated bars, and entertaining nightlife in Central Florida.

A large family gathers around the Christmas tree in Kissimmee

Kissimmee Vacation Homes for the Holidays

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

Nighttime scene at Old Town Kissimmee with visitors walking past the illuminated Mortem Manor haunted attraction and a glowing purple fountain in the foreground. — Evenings in Old Town come alive around the illuminated fountain and the haunting façade of Mortem Manor.

Haunted Attractions & Spooky Experiences in Kissimmee

Looking for a fright-filled Florida adventure? Explore Kissimmee’s haunted houses, ghost tours, historic cemeteries, and eerie after-dark experiences — perfect for Halloween season or spine-tingling fun year-round.

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 a couple of old-fashioned romantics or looking for a memorable day of fun, Kissimmee is the perfect place to spend this special holiday.

Red Mustang on display during a car show at Old Town Kissimmee — Catch a car show at Old Town Kissimmee

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.

ICEBAR Orlando: Unique Nightlife Experience

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

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.

Two people hold hands outdoors, with a diamond engagement ring visible against a softly blurred green background. — A quiet moment of connection, where love takes center stage before the journey ahead.

Why Kissimmee is the Perfect Pre-Honeymoon Destination

Wedding planning can be stressful, which is why many couples are escaping for a pre-honeymoon getaway. Discover why Kissimmee, Florida, is the perfect destination for romance, relaxation, and adventure before the big day.