Savor the moment in Kissimmee, where cozy cafés and stylish lounges set the scene for unforgettable conversations and connections.
Itinerary
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 97 results
1 - 10 of 97 results
Itinerary
Spring Break Like a Local Itinerary
If you’ve ever been to Florida (or you’re lucky enough to live here), you know just how beautiful and fun it is in spring — not to mention year-round! Read on to discover memorable local favorites and hidden gems for families.
Kayaking on Shingle Creek
Itinerary
A Local’s 3-Day Guide to a Romantic Getaway in Kissimmee
Join Orlando local Aliya Burshan as she shares her favorite ways for couples to relax, reconnect, and rediscover the magic of Kissimmee in just three unforgettable days.
The Wheel at ICON Park lights up the night sky, creating a stunning centerpiece for dining, entertainment, and fun near Kissimmee.
Itinerary
Baby-Friendly Kissimmee Vacation
Discover how easy — and genuinely fun — it can be to vacation with a baby in Kissimmee. This five-day family-friendly itinerary, inspired by Sam and Ryan Looney of Our Travel Passport, highlights top attractions, relaxing stays, and gentle adventures perfect for little travelers and their parents.
Fun and sunshine go hand in hand at Promenade at Sunset Walk in Kissimmee, where live entertainment, dining, and family-friendly vibes create the perfect Florida day out.
Itinerary
Discover the Joy of Accessible Travel with This 2-Day Kissimmee Itinerary
In Kissimmee, unforgettable experiences await visitors of all abilities from outdoor escapes to inclusive attractions that celebrate every traveler.
Savor the moment in Kissimmee, where cozy cafés and stylish lounges set the scene for unforgettable conversations and connections.
Itinerary
Romantic Kissimmee Weekend Getaway Guide
Planning a long weekend getaway in Kissimmee for just the two of you? Leave the daily grind (and the kids) behind and check out our vacation ideas for couples that make planning a romantic retreat effortless.
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.
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.
Enjoying drinks and food poolside at the Gaylord Palms Resort and Convention Center
Itinerary
A Three-Day Itinerary for a Quiet Getaway
There’s a quieter stretch on the Kissimmee calendar when the pace softens, the weather cooperates, and the destination feels refreshingly open. Fewer crowds, easier reservations, and more room to enjoy familiar favorites make this an ideal time for a long weekend or spontaneous escape. This three-day itinerary highlights how Kissimmee shines when timing does the work, and everything feels just a little easier.
Itinerary