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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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1 - 10 of 75 results

The exterior of Breeze, a restaurant with an open-air patio partially hidden by tropical plants and palm trees, with guests seated inside.

Pull up a chair and let the laid-back Florida breeze remind you why slowing down feels so good.

Article

Outdoor Dining in Downtown St. Cloud

Get ready to chow down and soak up the local vibes — we're diving into the heart of Downtown St. Cloud's outdoor dining scene!

Plated meal of egg tacos and potato wedges on a black plate at Loading...Gastrobrunch.

Tacos for breakfast at Loading...Gastrobrunch

Article

Start Your Day at These Downtown St. Cloud Brunch Spots

Discover cafés, bistros, and diners serving up a brunch menu that can't be beat in St. Cloud.
A powdered sugar–dusted croissant drizzled with strawberry sauce is served on a white plate inside a cozy café, with espresso equipment in the background.

Flaky, buttery, and finished with a sweet strawberry drizzle, this croissant is café comfort at its finest.

Article

Unveiling Downtown St. Cloud’s Dessert Delights

Downtown St. Cloud is at the center of big flavors that come in small, sweet packages! Nestled amidst the charming historic streets and friendly faces are tasty treats for dessert enthusiasts.
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.

Article

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.

Couple holding balloons and kissing in front of the Ferris wheel at ICON Park in Orlando, Florida..

Love is what makes the world go round at ICON Park, near Kissimmee, Florida.

Article

The Ultimate Guide to ICON Park

Soar to new heights at ICON Park! Our ultimate guide showcases thrilling attractions, great dining, and must-see experiences, including The Orlando Eye — offering unbeatable views of Orlando’s skyline.
Couple walking and smiling near the iconic Universal globe at Universal Orlando Resort on a sunny day in Central Florida.

Step into adventure at Universal Orlando Resort, where unforgettable thrills and world-famous attractions await just minutes from Kissimmee.

Article

The Ultimate Guide to Universal CityWalk Orlando

Experience the energy of Universal CityWalk with our ultimate guide! Explore must-visit restaurants, thrilling nightlife, and exciting attractions that make this entertainment district the perfect spot for a fun-filled night out in Kissimmee.
Family walking down sidewalk at the Promenade at Sunset Walk

Enjoy shopping, dining, and entertainment at Promenade at Sunset Walk

Article

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.
A bright vintage car drives past the colorful Old Town entrance arches in Kissimmee, with the Ferris wheel and visitors in the background.

Rolling into Old Town style, where classic cars and classic Florida fun cruise side by side.

Article

The Ultimate Guide to Old Town Entertainment District

Step back in time at Old Town Entertainment District! Our ultimate guide highlights classic car cruises, family-friendly attractions, unique shops, and delicious dining — making it the perfect destination for vintage vibes and endless fun.
1881 Restaurant and Bar

1881 Restaurant and Bar

Article

How Makinson Hardware Became the 1881 Restaurant & Bar

Explore the transformation of Makinson Hardware into the chic 1881 Restaurant & Bar, blending history with modern dining in Downtown Kissimmee.
Pink and gold donuts with sprinkles at Savvy Sweets in St. Cloud
Article

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!

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Experience Kissimmee recognizes the fundamental equality of all individuals and does not support the discriminatory or prejudicial treatment of any person, whether a resident or visitor to our destination. As the official tourism authority for Osceola County, FL, our goal is to always provide a welcoming environment and a positive experience for everyone. We embrace visitors from all backgrounds and cultures and do not discriminate against anyone based on race, color, creed, religion, sex, national origin, disability, sexual orientation, or gender identity.

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