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.

61 - 70 of 202 results

Two women pose playfully inside the Museum of Illusions, surrounded by mirrored walls and a geometric black-and-white ceiling that creates endless reflections. — Strike a pose and let reality bend a little at the Museum of Illusions, where reflections multiply the fun and every angle tells a different story.

Mind-Bending Fun at the Museum of Illusions

Cool optical illusions, brain-baffling scenes, and perplexing puzzles are just some of the immersive experiences at ICON Park’s Museum of Illusions in Orlando, just a short drive from Kissimmee, Florida.

Nighttime scene at Old Town Kissimmee featuring classic cars cruising down the brick streets, colorful shops, and visitors enjoying the lively atmosphere. — Experience the charm of Old Town Entertainment District, where classic car shows, family fun, and vintage vibes light up the night.

Timeless Fun at Old Town Entertainment District

In Kissimmee's Old Town Entertainment District, every day (and night) is a throwback — complete with car shows, a classic Ferris wheel, and live music.

Friends crossing a palm-lined street in Celebration, Florida, surrounded by colorful pastel buildings, parked cars, and clear blue skies. — Strolling through Celebration feels like stepping into a postcard. Pastel streets, palm-shaded sidewalks, and nowhere to rush except the next good moment.

Things to See & Do at Celebration Town Center

Horse-drawn carriage rides, family-friendly cooking classes, and authentic French macarons are just the beginning of the things to do in Celebration, Florida.

Top Restaurants in Celebration

From freshly baked biscuits to gourmet charcuterie plates to refreshing ice cream, Celebration's restaurants are sure to please.

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.

Top Things to Do at Promenade at Sunset Walk

Shop, dine, indulge. This entertainment hub in Kissimmee, just down the street from Margaritaville Resort Orlando, is ideal for a day of shopping and dining or a fun night out. See what's on tap.

Beach Vibes in Kissimmee: Sandy Escapes Without the Coastline

Discover sandy spots in Kissimmee where you can relax, play, and soak up the sun.

Oranges, cucumbers, and other earthly items for a spa day — Relax with a spa day in Central Florida

Time to Relax: Spas & Retreats in Kissimmee

Complete your Kissimmee vacation with lavish retreats and delightful days of indulgence at one of these soothing spas.

Colorful frozen margaritas lined up on an outdoor patio bar, garnished with lime and surrounded by cactus and flowers on a sunny day. — A vibrant lineup of frozen margaritas adds a splash of color to a sunny afternoon in Kissimmee’s lively dining scene.

Savor Mexican Flavors in Kissimmee

From authentic cuisine and salty margaritas to the local activities, you'll find a taste of Mexico in Kissimmee, Florida!

Angela Jones holding a glass and wearing a hat

A Kissimmee Staycation: A Local’s Guide to Outdoor Fun and Flavor

Join Central Florida local Angela Jones as she explores Kissimmee’s perfect mix of sunshine, adventure, and flavor, from kayaking and ziplining to tapas and tropical wine.

Couple walks through Universal Orlando Resort, smiling and waving near the iconic globe entrance. — Enjoy a sunny day exploring Universal Orlando Resort, one of the most thrilling and unforgettable attractions near Kissimmee, Florida.

A to Z in Kissimmee