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 family enjoys an airboat ride through the wetlands at Wild Florida, smiling and pointing at wildlife in the distance. — A family sets out on an exciting airboat adventure at Wild Florida, gliding across the headwaters of the Everglades to spot native wildlife and soak in Kissimmee’s natural beauty.

Unwrap the Joy of Kissimmee This Holiday Season

Discover how to make this holiday season memorable with unique gift ideas and unforgettable experiences in Kissimmee. Celebrate Small Business Saturday, explore charming shops, indulge in local flavors, and create lasting memories with your loved ones!

Three meeting attendees walking in the Gaylord Palms Convention Center — Gaylord Palms Resort & Convention Center

Discover Why Kissimmee Is the Ultimate Destination for Meetings and Conventions

Uncover the charm of Kissimmee with easy access, unique venues, and plenty of opportunities for fun in the sun!

Woman relaxing in pool

Relax and Recharge: Your Guide to Wellness in Kissimmee

Unwind and rejuvenate in Kissimmee with top resorts, serene outdoor experiences, and mindful activities. Discover the perfect balance of relaxation and adventure in Central Florida.

downtown st cloud — Downtown St. Cloud

Family Fun for Less Than $30 in Downtown St. Cloud

Discover cheap and family-friendly things to do in Downtown St. Cloud, Florida — all for $30 or less. Enjoy the park, local food, and unique shops in this Central Florida gem.

Oranges, cucumbers, and other earthly items for a spa day — Relax with a spa day in Central Florida

Time to Relax: Spas & Retreats in Kissimmee

Complete your Kissimmee vacation with lavish retreats and delightful days of indulgence at one of these soothing spas.

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.

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 multi-generational family arrives at a luxury vacation home in Kissimmee, Florida, smiling as they unpack luggage from their car on a sunny day. — A family begins their getaway at a spacious Kissimmee vacation home, perfect for creating memories together in the Vacation Home Capital of the World®.

Find Your Kissimmee Home Base: Stay, Work & Play

Grab your laptop, pack up the kids, and head to Central Florida, where you can stay, work, and play all in one spot.

People stroll through a lively nighttime street market in downtown St. Cloud, with vendor tents, warm string lights, and shops glowing along the brick-paved street. — Downtown St. Cloud comes alive during its nighttime market, where visitors can shop, stroll, and enjoy the local vibe under twinkling lights.

Discover the Artisans and Chefs of Kissimmee

From bold flavors to handcrafted goods, Kissimmee’s creative scene is powered by local artists, chefs, and entrepreneurs who bring passion to everything they make. Discover the tastemakers and businesses adding authentic flair to the destination.