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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Beaumont House in Downtown Kissimmee

Unveil the Secrets of Downtown Kissimmee’s Ghost Tour

Discover the haunted side of Kissimmee with Main Street Ghost Tours! Hear chilling tales, explore eerie spots, and enjoy a spooky adventure with friends and family.

Beaumont House in Downtown Kissimmee

Descubre los Espíritus en el Centro de Kissimmee

Descubre los lugares más embrujados de Kissimmee en un tour familiar lleno de historia, espíritus, y aventuras sobrenaturales. ¡Ideal para todas las edades!

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

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!

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.

Sip, Celebrate & Chill at ICEBAR Orlando

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

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.

Image of the St. Cloud Hunter Arms Hotel — Source: St. Cloud Main Street

Architecture Tour of St. Cloud’s History

As we stroll through the beautiful red brick streets of Downtown St. Cloud, Florida, we're not just walking through a city; we're journeying through time.

Gaylord Palms Christmas Snow Tubing

5 Spots to Experience Snow During the Holidays in Kissimmee

Experience the holiday season in Kissimmee with enchanting snow-filled activities. From nightly snowfall to ice sculptures and festive ice skating, discover the best spots for winter magic right in Central Florida.

Three women take a selfie at Boardwalk Plaza in Kissimmee

Savor & Stroll: A Historic Walking Tour of Downtown Kissimmee

Explore Downtown Kissimmee’s rich history and food scene on a walking tour. From iconic landmarks to delicious local bites, there’s always more to discover in the heart of Florida!

Two red helicopters parked on a sunny day at International Heli-Tours in Kissimmee, Florida, ready for scenic flights over Central Florida. — Take to the skies with International Heli-Tours and enjoy a bird’s-eye view of Kissimmee’s top attractions.

Top 10 Things to See on the Orlando Helicopter Adventures Tour

Whether you vacation in Central Florida every year or are planning your first family trip to Kissimmee, a bird’s-eye view of the area with the Orlando Helicopter Adventures Tour is a unique experience to start your vacation off right.