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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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31 - 40 of 41 results

Itinerary

7 Days of Shark Week in Kissimmee: How to Celebrate on Your Vacation

Celebrate your very own Shark Week at one or all of the shark attractions available here in Central Florida, from roller coasters to swimming beside sharks!
Itinerary

Celebrate Mother’s Day Weekend: 48 Hours of Family Fun in Kissimmee

Treat the special mom, mother figure, or loved one in your life to an unforgettable Mother’s Day weekend in Kissimmee. From relaxing spa moments to thrilling adventures, discover two days of exciting activities, delicious dining, and memorable experiences for the whole family.
Guests wearing crowns enjoy dinner and live entertainment at Medieval Times Dinner & Tournament in Kissimmee, Florida, where medieval knights and royal festivities create an unforgettable dining experience.

Enjoy a feast fit for royalty at Medieval Times Dinner & Tournament in Kissimmee, where jousting, cheering, and delicious dining make for a night of epic family fun.

Itinerary

A Perfect Day

Kissimmee is a dawn 'til dusk destination where visitors can go full throttle all day for a week and still feel like there will be even more to see and discover during the next visit.
Mother and daughter walking through Walt Disney World

Walt Disney World never fails to exceed expectations

Itinerary

A Three-Day Guide to Magic Kingdom Attractions

Why rush the magic? With this three-day guide, you’ll have plenty of time to ride the classics, meet your favorite characters, and still stop for a Mickey-shaped snack (or two) — all in the heart of sunny Florida.
Couple walking and smiling near the iconic Universal globe at Universal Orlando Resort on a sunny day in Central Florida.

Step into adventure at Universal Orlando Resort, where unforgettable thrills and world-famous attractions await just minutes from Kissimmee.

Itinerary

Kissimmee: A Tale of Two-Day Trips

Gather around friends, vacationers, and trip planners for an unforgettable tale of two-day trips — one that’s full of theme park joy and another all about outdoor fun!
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.

Itinerary

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.
Wrapped Christmas gift in front of Christmas tree in  Old Town Kissimmee

Find unique gifts for everyone on your list at Old Town Kissimmee

List

5 Best Ideas for Unique Gift Shopping in Kissimmee

Get your happy holidays on with this gift guide for all your beloved friends and family. This guide takes the hard choices out of finding the perfect gift. We’ll have you singing a love song as you go along, shopping in a Kissimmee wonderland.
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

List

Celebrate Small Business Saturday: 10 Must-Visit Local Gems in Kissimmee

The holidays are a time for giving, and what better way to spread the cheer than by supporting the local businesses that make Kissimmee truly special?

A person pulls a book out of a shelf.

Discover stories that enhance your Kissimmee adventure

List

Discover Must-Visit Bookstores in Kissimmee for a Literary Adventure

Enhance your Kissimmee adventure with a literary twist! Discover indie bookstores where stories unlock secret speakeasies, spark community connections, and unleash epic comic book quests.
Smiling girl in a sun shower with an umbrella.

Don't let a little rain ruin your Kissimmee vacation

List

6 Fun Vacation Things to do on a Rainy Day in Florida

Even in a downpour, there's family fun to be had in Kissimmee — just don't forget your umbrella!

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Experience Kissimmee recognizes the fundamental equality of all individuals and does not support the discriminatory or prejudicial treatment of any person, whether a resident or visitor to our destination. As the official tourism authority for Osceola County, FL, our goal is to always provide a welcoming environment and a positive experience for everyone. We embrace visitors from all backgrounds and cultures and do not discriminate against anyone based on race, color, creed, religion, sex, national origin, disability, sexual orientation, or gender identity.

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