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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41 - 50 of 86 results

41 - 50 of 86 results

Pink and gold donuts with sprinkles at Savvy Sweets in St. Cloud

A Culinary Bike Tour Through St. Cloud, Florida

Explore St. Cloud, FL: a haven for foodies & cyclists with scenic routes & diverse cuisine. Gear up for a unique bike-friendly culinary journey!

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.

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 the Artisans and Chefs of Kissimmee

From bold flavors to handcrafted goods, Kissimmee’s creative scene is powered by local artists, chefs, and entrepreneurs who bring passion to everything they make. Discover the tastemakers and businesses adding authentic flair to the destination.

A man and a woman eating in a restaurant — Old Town Entertainment District

Discover the Best Restaurants and Flavors at Old Town Entertainment District

From all-American classics to global favorites, Old Town Entertainment District offers a wide array of restaurants serving up satisfying dining experiences both savory and sweet.

Pottery at shops in Downtown Kissimmee

Discover the Heart of Puerto Rican Artistry in Downtown Kissimmee

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Musician performing live acoustic guitar and vocals at Crabby Bill’s in St. Cloud, Florida, with colorful seafood-themed posters in the background. — Enjoy live tunes and local flavor at Crabby Bill’s in St. Cloud.

Downtown St. Cloud’s Live Music Guide

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A smiling family poses for a selfie in front of a vintage-style mural in Downtown St. Cloud, Florida, depicting a historic scene with a woman in a car and the old Hotel St. Cloud. — Capturing memories in front of the historic Seminole Land Investment Company mural, one of many colorful, free-to-see murals in Downtown St. Cloud.

Downtown St. Cloud’s Most Captivating Murals

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A man squeezing lime into a jar to prepare Sangria

Savor the Flavors: Discover Global Cuisine in Kissimmee

Craving something bold, comforting, or delightfully unexpected? From Latin American street eats to Southern comfort food and international fine dining, Kissimmee, Florida, serves up a world of flavor in one delicious destination.

Colorful frozen margaritas lined up on an outdoor patio bar, garnished with lime and surrounded by cactus and flowers on a sunny day. — A vibrant lineup of frozen margaritas adds a splash of color to a sunny afternoon in Kissimmee’s lively dining scene.

Savor Mexican Flavors in Kissimmee

From authentic cuisine and salty margaritas to the local activities, you'll find a taste of Mexico in Kissimmee, Florida!

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!