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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31 - 40 of 365 results

31 - 40 of 365 results

Meeting Incentives — Margaritaville Resort Orlando

Meet the Partner Behind the Plan: How DMCs Elevate Meetings in Kissimmee

In Kissimmee, where business events meet natural landscapes and world-famous entertainment, agendas tend to do more than stay on schedule — they come to life. Here’s how working with a DMC helps planners unlock efficiency, creativity, and real return on experience.

Group of friends celebrating the holidays with sparklers and wine around a festive dinner table decorated with candles and Christmas lights. — Ring in the holidays with good food, bright lights, and even brighter smiles during your stay in Kissimmee.

Host Your Next Meeting in Kissimmee and Experience Holiday Magic

Combine productive meetings with the festive spirit of Central Florida’s top attractions and local holiday events.

Ami Vitale

Ami Vitale: A Journey Through Kissimmee’s Wild and Peaceful Places

In this episode of The Kissimmee Experience, award-winning photographer Ami Vitale joins host Jen Bonner to explore the beauty, balance, and wonder of Kissimmee’s natural world, from wildlife encounters at Disney’s Animal Kingdom to serene moments at Bok Tower Gardens.

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.

Welcome sign for Downtown Kissimmee, Florida

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Citrus Kiss — Citrus Kiss Charity Event

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A taco platter on a table — La Mexicana Restaurant, Kissimmee

La Mexicana: A Kissimmee Institution

How Odilia Alvarado and her family brought the flavors of Mexico’s mountains to the big, bold heart of Florida.

Bowls of Cuban food — Cuban dishes by Chef Amanda, Courtesy of Amanda Melendez

How a Kissimmee Food Truck is Redefining Cuban Comfort Food

Chef Amanda Melendez and her partner, Claudia Mena, built their following with a show-stopping seven-hour pork dish.

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

The Ultimate Guide to Promenade at Sunset Walk

Savor, shop, and stroll at Promenade at Sunset Walk! From top-tier dining and boutique shopping to live entertainment and special events, our ultimate guide covers everything you need for an unforgettable experience.

Two young children sit outside on bright turquoise chairs, enjoying ice cream at a table in front of a shop in Downtown St. Cloud, Florida. One child licks a waffle cone while the other eats with a spoon. — Sweet moments outside Pops Waffle & Ice Cream Shoppe in Downtown St. Cloud, where every cone comes with a smile.

Best Sweet Treats in Downtown St. Cloud

Craving something sweet? Discover the best dessert spots in Downtown St. Cloud, Florida, from colorful snowballs and waffle sundaes to chocolate-covered strawberries and more family-friendly treats.