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!

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.

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.

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.

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.

The Ultimate 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. Here are a few suggestions to make sure your Valentine’s Day is one to remember forever.

A mother and her young son enjoy a meal together while riding the Brightline train, with sunlight streaming through the window and a scenic view outside. — Enjoy a comfortable ride aboard Brightline, savoring snacks and scenery on the way to Kissimmee.

Getting Around Kissimmee by Train: Brightline, SunRail, and More

Discover how to ride the rails in Kissimmee, from fast and convenient train services like Brightline and SunRail to iconic theme park rides like the Walt Disney World® Monorail. Whether you're traveling around Central Florida or hopping aboard a rail-themed adventure, this guide has your ticket.

Epcot — Travel back in time on Spaceship Earth at Epcot

How to Travel to All the Major Theme Parks from Kissimmee

Kissimmee is moments away from the major theme parks. Here's how to check them all off your bucket list.

Anisa Benitez joins the cast of The Kissimmee Experience.

Anisa Benitez: Reconnect With Yourself In Kissimmee

Creative wellness advocate and content creator Anisa Benitez, known for her No Starving Artist podcast and mindful storytelling, explores Kissimmee’s relaxing side in The Kissimmee Experience — from goat yoga and spa days to sustainable wine tastings and quiet moments of reflection.

Woman relaxing on a massage table wrapped in a white towel, surrounded by soft lighting, flowers, and candles in a tranquil spa setting. — Unwind and recharge with a soothing spa experience in Kissimmee.

Bump Up the Fun with a Blissful Three-Day Babymoon in Kissimmee

Calling all moms-to-be! Plan the ultimate babymoon in Kissimmee with this three-day itinerary filled with relaxation, pampering, and gentle adventures. From spa treatments to scenic nature spots, discover why Kissimmee is the perfect destination for a blissful pre-baby escape.