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

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Sip and Savor: Local Drinks at Local Digs in Downtown Kissimmee

Explore Downtown Kissimmee’s best local bars, from craft cocktails to wine tastings. Discover unique drinks, lively atmospheres, and historic charm in every sip!

Family in Downtown Kissimmee — Downtown Kissimmee

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Thank you for completing your enrollment form for the Autism Travel Club training program.

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The 500th Cattle Run through Osceola County.

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Downtown Kissimmee: Where Kissimmee Cowboy Legends Come Alive

Step into the heart of Florida cowboy country by visiting Historic Downtown Kissimmee, a destination steeped in rich ranching history.

A couple stands arm in arm, looking up and pointing at a large, colorful floral mural painted on the side of a building in a sunny downtown setting. — Art stops you in your tracks. A shared moment, a bold mural, and a little magic found right on the street.

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Guide to a Perfect Day Date in Kissimmee

Looking for the perfect day date that can all be found in one place?

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Big Groups & Big Flavor: Group-Friendly Dining in Downtown Kissimmee

Discover the best group-friendly dining spots in Downtown Kissimmee. Perfect for celebrations, family get-togethers, and nights out with friends!

Kristen Lanier, owner of Madilynn’s Craft Coffee Shop in St. Cloud, Florida, standing behind the counter of her cozy, fall-themed café. — Kristen Lanier, owner of Madilynn’s Craft Coffee Shop in Downtown St. Cloud, shares her passion for locally roasted blends and community connection in every cup.

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Quality Brews & Local Charm Meet at Madilynns Craft Coffee Shop

Discover Madilynns Craft Coffee Shop, a cozy gem in Kissimmee where small-town charm meets exceptional coffee. From freshly roasted beans to locally made pastries, this family-owned spot delivers a one-of-a-kind experience that keeps locals and visitors coming back for more.

Shoppers stroll along a palm-lined outdoor shopping promenade, passing luxury storefronts while carrying branded shopping bags on a sunny day. — Sunlit strolls and stylish finds turn shopping into a vacation-worthy pastime.

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The Ultimate Shopping Day at Orlando Vineland Premium Outlets®

Orlando Vineland Premium Outlets® is Central Florida’s only upscale, open-air outlet shopping destination, featuring a dazzling mix of boutique-style luxury and must-have brands.