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.

1 - 10 of 49 results

Entrance to Orlando Vineland Premium Outlets

Your Complete Guide to Orlando Vineland Premium Outlets

Welcome to shopper’s paradise, where fashion fantasies come to life and luxury items are at your fingertips.

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

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.

Madilynns Craft Coffee Shop

Celebrating Female-Led Businesses in Downtown St. Cloud

Among the many reasons to celebrate this district near Kissimmee, Florida, is the presence of several successful women-owned businesses that have made their mark on the town.

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.

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.

Bottles of raw natural honey from 3Beez Honey Farm in St. Cloud, Florida, displayed on a shelf with decorative bee charms tied around the tops. — Local flavor at its sweetest. 3Beez Honey Farm brings Florida sunshine to every jar with small-batch, raw natural honey crafted right in St. Cloud.

Shop Local Across Downtown Kissimmee and St. Cloud

Experience the enchantment of charming, local Downtown Kissimmee and St. Cloud shops. Immerse yourself in unique, community-rooted businesses, and discover the joy of supporting locally-owned shops in Florida.

1881 Restaurant and Bar

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.

Minch Coffee Co./Orlando Cat Cafe

Minch Coffee Co.: Where Community, Coffee, and Cats Come Together

This local coffee shop combines expertly brewed coffee with a unique partnership at the Orlando Cat Café, and guests can relax, sip, and even adopt a furry friend.

A family enjoys an airboat ride through the wetlands at Wild Florida, smiling and pointing at wildlife in the distance. — A family sets out on an exciting airboat adventure at Wild Florida, gliding across the headwaters of the Everglades to spot native wildlife and soak in Kissimmee’s natural beauty.

Unwrap the Joy of Kissimmee This Holiday Season

Discover how to make this holiday season memorable with unique gift ideas and unforgettable experiences in Kissimmee. Celebrate Small Business Saturday, explore charming shops, indulge in local flavors, and create lasting memories with your loved ones!

The Stained Glass Lady St. Cloud

Celebrating Women-Owned Businesses in Downtown St. Cloud

Explore Downtown St. Cloud's women-owned businesses. They provide a diverse range of services for locals and tourists including creating stained glass, unique clothing finds, and delightful, sweet treats.

Playground at Kissimmee Lakefront Park

Day of Wellness and Relaxation Across Downtown Kissimmee & St. Cloud

Discover a day of relaxation in Downtown Kissimmee and St. Cloud, Florida. From lakeside strolls to yoga, tasty bites, and self-care, unwind in style.