Things to Do in Kissimmee, Florida, A Two-Day Itinerary

Planning a sunshine-filled vacation near Orlando? Head to Kissimmee! From world-famous theme parks to airboat rides and historic charm, Kissimmee is the perfect family-friendly hub. Enjoy easy access to Walt Disney World, outdoor adventures, and vibrant dining, all with that laid-back Florida vibe. Our guide is packed with things to do in Kissimmee, Florida. The 2-day itinerary includes something for everyone, from history to water park fun.

Kissimmee, FL Highlights:

• For Thrill-Seekers: Explore Walt Disney World Resort – I’ve spent entire days hopping between the parks, and trust me—you’ll never run out of things to do. It’s only minutes from Kissimmee, and if you’re into rides and magic, you’re in for a treat.
• For Outdoor Lovers: Ride with Boggy Creek Airboat Adventures – I loved gliding through the wetlands and spotting gators up close. If you enjoy nature and a little excitement, you’ll love this ride as much as I did.
• For History Fans: Visit Pioneer Village at Shingle Creek – When I wanted a quieter day, this living history museum was a peaceful and fascinating stop. You’ll get a feel for 1800s Florida life, and I think you’ll appreciate the craftsmanship on display.
• For Families: Stroll through Old Town Kissimmee – I brought friends here for a fun, low-key evening. You can ride vintage rides, check out the weekly car show, and grab a bite—it’s easygoing and full of charm.
• For Animal Fans: Feed giraffes at Wild Florida – If you’re anything like me, you’ll be thrilled by the up-close animal encounters. It’s a safari park, zoo, and swamp tour all in one. I could’ve stayed there all day.

Best Time to Visit Kissimmee, FL

If you want the most pleasant weather, I suggest going between October and April. That’s when I usually visit to avoid the summer crowds and heat. You’ll get warm, sunny days—perfect for exploring without constantly seeking shade. But if you’re up for splashy summer fun, water parks and pool days are great between May and September—just pack for heat and afternoon showers.

How to Get to Kissimmee, FL

• If you are traveling by car: I’ve driven in using I-4 and U.S. 192—it’s a smooth route, and Kissimmee’s just 30 minutes south of Orlando.
• By Air: I usually fly into Orlando International Airport (MCO)—it’s only about 25 minutes away. You could also consider Sanford Airport if you find a good deal, though it’s a bit farther.
• By Train: You can hop on Amtrak or SunRail—I’ve used both to get into downtown Kissimmee, and it’s a relaxed, scenic option if you prefer not to drive.

Where to Stay in Kissimmee, FL

• Recommended for Families: Margaritaville Resort Orlando – I stayed here with my family and loved the pool and tropical vibe. The free shuttles to the parks made everything easy—you’ll barely need your car.
• For Couples: Magic Village Yards – When I wanted a quiet, upscale place, this villa-style resort delivered. You’ll love the peaceful surroundings and spacious, beautifully decorated rooms.
• For Budget Travelers: Comfort Suites Maingate East – I’ve recommended this to friends traveling on a budget. It’s clean, comfortable, and the location near Old Town makes it easy to explore without spending a lot.

If want to experience Kissimmee on a tour, book one of these:

Create lasting memories with a Private Photo Session with a Local Photographer in Kissimmee.
Go on a Private 8-hour Lake Toho Fishing Charter Near Kissimmee.
Or check out Kissimmee and St. Cloud Beach Tour on All Electric Trike

Day 1 in Kissimmee, Florida: Begin at the Museum of Military History in the morning, followed by a walk around Lake Tohopekaliga. Have a quick lunch followed by an airboat ride through wetlands. In the evening, enjoy a stroll through the charming Old Town.