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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People stroll through a lively nighttime street market in downtown St. Cloud, with vendor tents, warm string lights, and shops glowing along the brick-paved street. — Downtown St. Cloud comes alive during its nighttime market, where visitors can shop, stroll, and enjoy the local vibe under twinkling lights.

Discover Local Shopping at the Downtown St. Cloud Monthly Market

The Downtown St. Cloud Monthly Market is a lively community event held every fourth Wednesday of the month, where locals and visitors gather to enjoy live music, browse unique local vendors, and indulge in delicious eats — all in the heart of charming historic St. Cloud.

Wild Florida Drive Through Safari

Visit Wild Florida Adventure Park for Florida’s Best Wildlife Adventures

See the natural side of the Sunshine State at Wild Florida Adventure Park, an outdoor adventure park in Kissimmee. Ride an airboat, stroll around to see animals, or take a drive through the Safari Park.

Welcome to Kissimmee Sign in Downtown Kissimmee — Welcome to Kissimmee

Historical Sites in Central Florida All History Buffs Should Visit

From iconic landmarks to intriguing museums and solemn memorials, the area offers a treasure trove of historical sites that every history buff should explore.

Hand holding freshly picked strawberries beside rows of strawberry plants in a u-pick field. — Fresh from the field and still warm from the Florida sun, these hand-picked strawberries capture the simple joy of slowing down and savoring the season.

U-Pick Farms Near Kissimmee: Where to Pick Strawberries, Citrus, and Flowers in Central Florida

Step into harvest season at these Central Florida u-pick farms near Kissimmee, where visitors can gather strawberries, blueberries, citrus, and flowers straight from the field.

Get up close with colorful wildlife in Kissimmee, where every encounter — from playful flamingos to majestic sea life — sparks wonder and smiles.

SeaWorld Orlando's All-Day Dining Plan

Review the information and decide for yourself whether SeaWorld's All-Day Dining Deal is worth the price.

Fun Spot Kissimmee — Fun Spot America - Kissimmee

The Ultimate Guide to Fun Spot America – Kissimmee

Looking for classic amusement park fun without the full-day commitment? Fun Spot America – Kissimmee delivers high-speed coasters, multi-level go-karts, and nostalgic midway games, all with the flexibility to ride your way.

Two children dressed in Halloween costumes pose playfully with a LEGO® mummy character during Brick-or-Treat at LEGOLAND® Florida Resort. — Spooky fun for the whole family! Kids can show off their costumes alongside a LEGO® mummy at Brick-or-Treat at LEGOLAND® Florida Resort.

Fall Events, Halloween Fun & Things to Do in Kissimmee

Celebrate the season with unforgettable fall events in Kissimmee, from family-friendly festivals and foodie favorites to haunted houses and Halloween thrills at top theme parks.

Family walking down sidewalk at the Promenade at Sunset Walk — Enjoy shopping, dining, and entertainment at Promenade at Sunset Walk

Beyond the Theme Parks: Outdoor Adventures and Fun Things To Do in Kissimmee

Immerse yourself in a world of outdoor adventures, entertainment districts, and fun-filled shopping and dining in Kissimmee.

Group of people sitting, laughing and eating.

Adventure & Impact: Best Team-Building Activities in Kissimmee

Discover unforgettable team-building experiences in Kissimmee — where thrilling adventures, meaningful CSR opportunities, and unforgettable memories strengthen your team and leave a lasting impact.

A couple enjoys drinks and conversation at a stylish café inside the ette hotel in Kissimmee, Florida, seated together on a modern tan sofa under soft ambient lighting. — Savor the moment in Kissimmee, where cozy cafés and stylish lounges set the scene for unforgettable conversations and connections.

Romance & Adventure: A 4-Day Kissimmee Getaway Itinerary

Discover how to plan a romantic and adventure-filled 4-day getaway in Kissimmee, featuring top date spots, outdoor activities, dining, and must-try attractions across Central Florida.