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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White building with historic sign outside in St. Cloud.

The History Behind Downtown St. Cloud: The Soldier City

The history of Downtown St. Cloud effortlessly blends a rich history, traditions, and a close-knit community.

Musician performing live acoustic guitar and vocals at Crabby Bill’s in St. Cloud, Florida, with colorful seafood-themed posters in the background. — Enjoy live tunes and local flavor at Crabby Bill’s in St. Cloud.

Downtown St. Cloud’s Live Music Guide

Downtown St. Cloud is a small town with a big personality. Also known as Soldier City, the city of St. Cloud is filled with history, food, and entertainment.

Pink and gold donuts with sprinkles at Savvy Sweets in St. Cloud

A Culinary Bike Tour Through St. Cloud, Florida

Explore St. Cloud, FL: a haven for foodies & cyclists with scenic routes & diverse cuisine. Gear up for a unique bike-friendly culinary journey!

downtown st cloud — Downtown St. Cloud

Local Vendors at the Monthly Market in Downtown St. Cloud

Under the starlit sky, historic brick streets are blocked off to create a vibrant atmosphere filled with local makers as you roam the small town for unique finds and seasonal goodies.

Welcome sign for Downtown Kissimmee, Florida

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Wedding at First United Methodist Church in Downtown Kissimmee.

Downtown Kissimmee Wedding Venues For Your Perfect Day

Couples seeking a beautiful wedding venue can look no further than Downtown Kissimmee.

couple pointing at mural located in Downtown Kissimmee — "The Wild Ones" presented by Osceola Arts

Guide to a Perfect Day Date in Kissimmee

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

Kissimmee Lakefront Park Pavillion

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!

Family in Downtown Kissimmee — Downtown Kissimmee

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A man sets a golf ball on the tee

Kissimmee Bay Country Club

Step onto Kissimmee Bay Country Club’s golf course and you’ll feel like a local.