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 28 results

1 - 10 of 28 results

A bartender pours a beer at Celebration Brewing Co. — Enjoy a crisp beer at Celebration Brewing Co. in Celebration, Florida.

Local Spots in Downtown Kissimmee & St. Cloud

Explore downtown Kissimmee and St. Cloud for local boutiques, elevated bars, and entertaining nightlife in Central Florida.

ICEBAR Orlando: Unique Nightlife Experience

At ICEBAR Orlando, discover a winter wonderland in Florida, complete with ice sculptures, ice furniture, and ice cocktail glasses.

Red mocktail in a nest-like arrangement from the ette hotel.

Explore Kissimmee’s Best Zero-Proof Drinks and Alcohol-Free Experiences

Discover refreshing zero-proof drinks and alcohol-free experiences throughout Kissimmee’s vibrant culinary and entertainment scene. From handcrafted mocktails to family-friendly hangouts, you’ll find plenty of flavorful ways to sip, savor, and celebrate. No alcohol required.

Central Florida Beer Guide: Lager Than Life Local Brews

Discover the best local breweries and beer experiences in Central Florida. Explore Kissimmee’s top spots for craft brews, taprooms, and unique beer-inspired fun on your next getaway.

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.

Romance & Adventure: A 4-Day Kissimmee Getaway Itinerary

Discover how to plan a romantic and adventure-filled 4-day getaway in Kissimmee, featuring top date spots, outdoor activities, dining, and must-try attractions across Central Florida.

Aseky Family Images

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.

Two people exploring Shingle Creek on yellow kayaks — Kayaking on Shingle Creek

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.

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.

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.