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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21 - 30 of 30 results

21 - 30 of 30 results

Wild Florida airboat with people riding on it gliding on top of water surrounded by lush greenery.

4-Day Family Vacation in Kissimmee: Airboats, Alligators & Outdoor Adventures

Discover how a four-day Kissimmee getaway delivers unforgettable family fun from airboat rides and wildlife encounters to kid-friendly attractions and spacious vacation homes. Inspired by creator Aseky Bonnaire’s trip, this itinerary shows you how to plan a stress-free, adventure-filled vacation your whole family will love.

Wooden boardwalk winding through a peaceful cypress swamp surrounded by tall trees at Gatorland near Kissimmee, Florida. — Explore the natural side of Gatorland along its scenic boardwalk, where towering cypress trees and still waters showcase the beauty of Florida’s wetlands.

Influencer Itinerary: 4 Days of Outdoor Adventure & Indoor Leisure

Discover how Florida Instagrammer Angela Jones and her husband, Matthew Lewis, embraced the best of Kissimmee—from serene vacation-home downtime to standout moments in nature, dining, and after-dark fun. Their trip showcases just how effortlessly a Kissimmee getaway can balance relaxation with adventure.

Woman relaxing on a massage table wrapped in a white towel, surrounded by soft lighting, flowers, and candles in a tranquil spa setting. — Unwind and recharge with a soothing spa experience in Kissimmee.

Bump Up the Fun with a Blissful Three-Day Babymoon in Kissimmee

Calling all moms-to-be! Plan the ultimate babymoon in Kissimmee with this three-day itinerary filled with relaxation, pampering, and gentle adventures. From spa treatments to scenic nature spots, discover why Kissimmee is the perfect destination for a blissful pre-baby escape.

Emily Kinney wears sunglasses and smiles while gently greeting a horse at First Nature Ranch in Kissimmee. — New friends and sunny skies. Emily Kinney gets acquainted with her equine co-star at First Nature Ranch.

Emily Kinney’s Kissimmee Soundtrack

Actress and musician Emily Kinney explores Kissimmee in search of quiet moments, creative sparks, and a little rhythm along the way.

A family enjoying an outdoor meal together at a restaurant patio, smiling and talking over drinks and plates of food on a sunny day. — Good food, good laughs, and that laid-back Florida patio glow. Moments like this taste even better than the barbecue.

3 Spots with the Best Live Entertainment in Downtown Kissimmee

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Foxtail Coffee Co. Hunter's Creek

Caffeinated in Kissimmee: Discover the Best Local Coffee Shops

From quick caffeine fixes to cozy hangouts, explore Kissimmee's local coffee spots that keep you energized between all the fun.

Three women take a selfie at Boardwalk Plaza in Kissimmee

Savor & Stroll: A Historic Walking Tour of Downtown Kissimmee

Explore Downtown Kissimmee’s rich history and food scene on a walking tour. From iconic landmarks to delicious local bites, there’s always more to discover in the heart of Florida!

A close-up of a restaurant table setting featuring a dish of fried calamari topped with peppers and herbs, accompanied by drinks including water, a cocktail, and a glass of sparkling wine. — When the flavors are bold and the company’s good, the meal becomes its own little celebration.

Top 9 On-Site Restaurants in Kissimmee Resorts

Whether you love to dine in a casual setting with the whole family or enjoy dressing up for a romantic dinner, the resorts in Kissimmee, Florida, have it all.

Three pizza's on a wooden table beside a jar full of salt and a glass full of juice. — Explore endless pizza opportunities in Central Florida / @kndvg

10 of the Best Pizza Places in Kissimmee

Find your perfect slice at these top spots for pizza across the Kissimmee area.

Two men and a woman walk the water front in Celebration. — Enjoy your next meeting or event in sunny Florida.

9 Hotels in Kissimmee for Hosting Your Next Meeting or Event

Where business meets innovation — and a bit of fun! Discover top meeting hotels in Kissimmee with flexible spaces, modern amenities, and unique venues for your next event.