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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11 - 20 of 25 results

11 - 20 of 25 results

Three women take a selfie at Boardwalk Plaza in Kissimmee

See, Eat, and Explore Downtown Kissimmee for Less Than $30

Explore Downtown Kissimmee without spending a fortune. A full day of adventure, food, and family fun is waiting — all for less than $30!

Cake pops covered in sprinkles. — Crave-worthy candied apples make a delightful fall treat / Event Octoberfest

Six Instagram-Worthy Kissimmee Treats

When it comes to Instagrammable sweets, these are just a few of the fabulous desserts you'll find on the menu in and around Kissimmee.

Tasty Gluten-Free and Vegan Options in Kissimmee Restaurants

Explore Kissimmee's best gluten-free and vegan dining! From cozy cafes to family-friendly spots, enjoy a variety of tasty, inclusive options for everyone.

St. Cloud Lake Toho

Celebrate Earth Day in Kissimmee

Looking for ways to celebrate Earth Day in Florida? Head to Kissimmee for family-friendly eco adventures, outdoor fun, and nature experiences that make every moment a little greener.

Friends enjoying St. Patrick's Day

Where to Celebrate St. Patrick's Day in Kissimmee

Celebrate St. Patrick's Day in a sun-filled, fun-filled destination that'll make your friends and family green with envy!

A white ceramic coffee mug with a black circle and the words, XO Coffee in white letters in the center, on a wooden tabletop. In the background, there is a faint outline of a neon sign. — Enjoy a coffee while watching tattoo artists at work at XO Coffee Shop.

XO Coffee Shop: Fresh Brews & Tattoos

XO Coffee Shop in Kissimmee blends great coffee with creative tattoo art, offering a welcoming space for everyone. Experience the perfect mix of caffeine, creativity, and community.

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.

Kristen Lanier, owner of Madilynn’s Craft Coffee Shop in St. Cloud, Florida, standing behind the counter of her cozy, fall-themed café. — Kristen Lanier, owner of Madilynn’s Craft Coffee Shop in Downtown St. Cloud, shares her passion for locally roasted blends and community connection in every cup.

Quality Brews & Local Charm Meet at Madilynns Craft Coffee Shop

Discover Madilynns Craft Coffee Shop, a cozy gem in Kissimmee where small-town charm meets exceptional coffee. From freshly roasted beans to locally made pastries, this family-owned spot delivers a one-of-a-kind experience that keeps locals and visitors coming back for more.

A couple walks hand in hand along the dock outside The BOATHOUSE at Disney Springs, smiling under a bright, partly cloudy sky with the restaurant’s tower and outdoor umbrellas in the background. — Strolling into golden-hour bliss at The BOATHOUSE in Disney Springs, where waterfront dining and warm-weather daydreams pair perfectly.

Valentine's Day Guide to Kissimmee

Whether you’re longtime romantic partners or a new couple looking for a fun, memorable day, Kissimmee is the perfect place to spend the day with your Valentine.

A large family gathers around the Christmas tree in Kissimmee

Kissimmee Vacation Homes for the Holidays

Explore the vacation home rentals available in Central Florida to find the perfect spot to celebrate this holiday season.