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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201 - 210 of 246 results

201 - 210 of 246 results

Knights in Tunnel

Kissimmee Dinner Show Roundup

Dinner is never a bore when there’s a high-seas pirate escapade, aerial artistry, or swordplay involved. See top spots in Kissimmee for a deliciously entertaining dinner show.

A family enjoying a picnic on a blanket near a brick lighthouse at a waterfront park, sharing food and conversation under a bright blue sky. — Sunshine, sandwiches, and stories shared by the water. This lighthouse picnic lights up the day in all the best ways.

Kissimmee Like a Local

From delicious dining and fun weekly attractions to appreciating the great outdoors, we’ve rounded up Kissimmee locals’ favorite things to do in this sunny part of Central Florida.

Family Driving In Car On Road Trip — Make this roadtrip your family's favorite / Getty Images

Kissimmee Road Trip Bingo

Our Kissimmee Bingo cards highlight local wildlife, signs, and transportation, and are sure to make your road trip to Central Florida just as fun as the destination itself is.

Family walking down sidewalk at the Promenade at Sunset Walk — Enjoy shopping, dining, and entertainment at Promenade at Sunset Walk

Kissimmee Shopping Guide

From outlet malls to specialty boutiques to local favorites and national brands, there's a shopping experience for everyone in Kissimmee. Find out everything you need to know in this handy guide.

Scenic view of a calm waterway surrounded by tall grasses and lily pads at a nature preserve in Kissimmee, Florida. — Peaceful wetlands filled with lily pads and native Florida vegetation offer a glimpse of Kissimmee’s natural beauty and thriving ecosystems.

Celebrate Earth Day in Kissimmee

Looking for ways to celebrate Earth Day in Florida? Head to Kissimmee for family-friendly eco adventures, outdoor fun, and nature experiences that make every moment a little greener.

A performer in a vibrant Mardi Gras costume with purple, green, and gold feathers smiles and dances during a nighttime parade. — Mardi Gras magic comes to life in a swirl of color, music, and high-energy celebration.

How to Celebrate Carnival in Osceola County

Explore some of Florida's best eateries during Carnival! Explore Downtown St. Cloud and Kissimmee's top restaurants for a festive and flavorful experience.

Friends enjoying St. Patrick's Day

Where to Celebrate St. Patrick's Day in Kissimmee

Celebrate St. Patrick's Day in a sun-filled, fun-filled destination that'll make your friends and family green with envy!

Two children relaxing together on a blue inner tube as they float along a lazy river, surrounded by lush greenery and calm, shallow water. — Slow laps, sunny laughs, and nowhere else to be. This is what vacation mode looks like when the current sets the pace.

You Deserve a Spring Break Vacation!

Plan your dream spring-break getaway to Kissimmee, Florida, with these helpful tips.

Exterior of Mall at Millenia with palm trees and blue sky — Indulge in luxury shopping at the Mall at Millenia

The Mall at Millenia: Luxe Shopping & Dining

Find your favorite designer stores, a mix of great dining, and top-tier services from self-care to personal styling at The Mall at Millenia in Orlando.

The Ferris Wheel at Old Town Entertainment District on a beautiful cloud free day — Take your kids on the Ferris wheel at Old Town Entertainment District

Free Things to Do in Kissimmee

Looking for affordable fun in Central Florida? From outdoor adventures to cultural treasures, discover free things to do in Kissimmee beyond the theme parks.