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.
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1 - 10 of 22 results
1 - 10 of 22 results
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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
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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.
Soar above it all at Gatorland with the Screamin’ Gator Zip Line, a thrilling way to take in Kissimmee’s wild side from high above the park’s iconic alligator breeding marsh.
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Family-Friendly Kissimmee Itinerary
Looking for the perfect family escape without traveling far? Motherhood & Lifestyle Influencer @IzzyRose and her young family discovered just that in Kissimmee, a fun-filled destination right in the center of it all, just two hours from their home in St. Augustine.
A family-friendly airboat ride in Kissimmee
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Tiny Travelers, Big Adventures: A Four-Day Family Escape to Kissimmee
Looking for a family vacation that keeps every kid smiling and every parent sane? Take inspiration from a recent four-day trip to Kissimmee, where dermatologist and Florida mom Dr. Laura Scott and her crew explored the destination’s most playful parks, attractions, trails, and stays. From outdoor adventures to splash-worthy fun, here’s how families of all sizes can experience Kissimmee at its best.
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4-Day Family Vacation in Kissimmee: Airboats, Alligators & Outdoor Adventures
Discover how a four-day Kissimmee getaway delivers unforgettable family fun from airboat rides and wildlife encounters to kid-friendly attractions and spacious vacation homes. Inspired by creator Aseky Bonnaire’s trip, this itinerary shows you how to plan a stress-free, adventure-filled vacation your whole family will love.
Explore the natural side of Gatorland along its scenic boardwalk, where towering cypress trees and still waters showcase the beauty of Florida’s wetlands.
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Influencer Itinerary: 4 Days of Outdoor Adventure & Indoor Leisure
Discover how Florida Instagrammer Angela Jones and her husband, Matthew Lewis, embraced the best of Kissimmee—from serene vacation-home downtime to standout moments in nature, dining, and after-dark fun. Their trip showcases just how effortlessly a Kissimmee getaway can balance relaxation with adventure.
The Wheel at ICON Park lights up the night sky, creating a stunning centerpiece for dining, entertainment, and fun near Kissimmee.
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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.
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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.
Buckle up for an awe-inspiring animal adventure at Wild Florida's Drive-thru Safari Park.
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