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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11 - 20 of 27 results

11 - 20 of 27 results

Wild Florida airboat with people riding on it gliding on top of water surrounded by lush greenery.

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.

Wooden boardwalk winding through a peaceful cypress swamp surrounded by tall trees at Gatorland near Kissimmee, Florida. — Explore the natural side of Gatorland along its scenic boardwalk, where towering cypress trees and still waters showcase the beauty of Florida’s wetlands.

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.

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.

Families enjoying outdoor entertainment at Promenade at Sunset Walk in Kissimmee, Florida, with a woman and young girl hula-hooping under palm trees on a sunny afternoon. — 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.

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.

Family in a white SUV observes a herd of wildebeest up close during a drive-thru safari experience at Wild Florida in Kenansville, Florida. — Buckle up for an awe-inspiring animal adventure at Wild Florida's Drive-thru Safari Park.

3-Day Accessible-Friendly Itinerary

From shopping to zip lining and more, everyone can enjoy these accessibility-focused activities in Kissimmee!

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!

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.

A couple enjoys drinks and conversation at a stylish café inside the ette hotel in Kissimmee, Florida, seated together on a modern tan sofa under soft ambient lighting. — Savor the moment in Kissimmee, where cozy cafés and stylish lounges set the scene for unforgettable conversations and connections.

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.

A young adventurer navigates a suspended rope obstacle course at Tree Trek Adventure Park, balancing across hanging wooden logs surrounded by tall trees. — A little balance, a lot of bravery, and views from the treetops. Tree Trek Adventure Park is where outdoor fun climbs to new heights.

Itinerary: 36 Hours of Family Fun in Kissimmee, Florida

With world-famous theme parks, thrilling outdoor adventures, and countless attractions right in our backyard, Kissimmee is the place for an unforgettable getaway. Here's how to make the most of a quick family trip.

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.

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!