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.

0

1 - 10 of 23 results

1 - 10 of 23 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.

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.

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.

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.

Friends and family toast to a meal in Kissimmee

Alternatives to Cooking Thanksgiving Dinner

Thinking of doing something a little different this year? Here are a few ways to make this year's Thanksgiving unforgettable, rather than predictable!

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 young boy joyfully jumps into a private vacation home pool while a woman relaxes on a yellow float, smiling toward him. The luxury home’s patio and outdoor seating area sit in the background. — Cannonballs, sunshine, and your own private pool. This is vacation freedom, Kissimmee-style.

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.

Christmas tree in the Gaylord Palms Resort

Christmas at Gaylord Palms 2025: Rudolph the Red-Nosed Reindeer™ and More Holiday Fun

From Nov. 14, 2025 to Jan. 7, 2026, Christmas at Gaylord Palms transforms the resort into a holiday wonderland featuring Rudolph the Red-Nosed Reindeer™, dazzling lights, and family fun.