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 34 results

1 - 10 of 34 results

Minch Coffee Co./Orlando Cat Cafe

Minch Coffee Co.: Where Community, Coffee, and Cats Come Together

This local coffee shop combines expertly brewed coffee with a unique partnership at the Orlando Cat Café, and guests can relax, sip, and even adopt a furry friend.

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!

A white ceramic coffee mug with a black circle and the words, XO Coffee in white letters in the center, on a wooden tabletop. In the background, there is a faint outline of a neon sign. — Enjoy a coffee while watching tattoo artists at work at XO Coffee Shop.

XO Coffee Shop: Fresh Brews & Tattoos

XO Coffee Shop in Kissimmee blends great coffee with creative tattoo art, offering a welcoming space for everyone. Experience the perfect mix of caffeine, creativity, and community.

Two baristas at Piccolo Coffee Co.’s mobile espresso bar, smiling and preparing drinks during an outdoor event in Central Florida, with a full setup including syrups, coffee grinder, and custom cups. — From espresso shots to unforgettable moments, Piccolo Coffee Co. is all smiles—and all flavor—at events throughout Kissimmee and Central Florida.

Piccolo Coffee Co.: The Specialty Coffee Cart That Comes to You

Piccolo Coffee Co. brings handcrafted coffee and heartfelt hospitality to Kissimmee and beyond. With a mobile coffee bar and a passion for creating meaningful moments, they serve specialty drinks and cozy vibes that elevate any event or everyday escape across Central Florida.

Family Driving In Car On Road Trip — Make this roadtrip your family's favorite / Getty Images

Kissimmee Road Trip Bingo

Our Kissimmee Bingo cards highlight local wildlife, signs, and transportation, and are sure to make your road trip to Central Florida just as fun as the destination itself is.

The Ferris Wheel at Old Town Entertainment District on a beautiful cloud free day — Take your kids on the Ferris wheel at Old Town Entertainment District

Free Things to Do in Kissimmee

Looking for affordable fun in Central Florida? From outdoor adventures to cultural treasures, discover free things to do in Kissimmee beyond the theme parks.

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 longtime romantic partners or a new couple looking for a fun, memorable day, Kissimmee is the perfect place to spend the day with your Valentine.

A man squeezing lime into a jar to prepare Sangria

Savor the Flavors: Discover Global Cuisine in Kissimmee

Craving something bold, comforting, or delightfully unexpected? From Latin American street eats to Southern comfort food and international fine dining, Kissimmee, Florida, serves up a world of flavor in one delicious destination.

Group of 3 girlfriends walking down the sidewalk in downtown Kissimmee examining their shopping bags — Score the find of a lifetime shopping in Downtown Kissimmee

Stay Chill in Downtown Kissimmee: Your Guide to Indoor Activities

Discover the top indoor activities in Downtown Kissimmee, from unwinding at the library to dining at local hotspots. Get your guide to the perfect day of relaxation.

Tasty Gluten-Free and Vegan Options in Kissimmee Restaurants

Explore Kissimmee's best gluten-free and vegan dining! From cozy cafes to family-friendly spots, enjoy a variety of tasty, inclusive options for everyone.