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.

0

1 - 10 of 33 results

1 - 10 of 33 results

Kyla Kenedy sits to eat a plate of tacos while two cameramen film the shot. — Behind the scenes of the personal chef experience at Kyla's vacation home.

Kyla Kenedy: Top Luxury Experiences Around Kissimmee

Discover some of the most luxurious ways to unwind, indulge, and elevate your getaway in Kissimmee. Episode two of The Kissimmee Experience highlights several standout experiences that showcase the destination’s upscale side.

Two young children sit outside on bright turquoise chairs, enjoying ice cream at a table in front of a shop in Downtown St. Cloud, Florida. One child licks a waffle cone while the other eats with a spoon. — Sweet moments outside Pops Waffle & Ice Cream Shoppe in Downtown St. Cloud, where every cone comes with a smile.

Best Sweet Treats in Downtown St. Cloud

Craving something sweet? Discover the best dessert spots in Downtown St. Cloud, Florida, from colorful snowballs and waffle sundaes to chocolate-covered strawberries and more family-friendly treats.

Two young children sit outside on bright turquoise chairs, enjoying ice cream at a table in front of a shop in Downtown St. Cloud, Florida. One child licks a waffle cone while the other eats with a spoon. — Sweet moments outside Pops Waffle & Ice Cream Shoppe in Downtown St. Cloud, where every cone comes with a smile.

Top Dessert Spots in Downtown St. Cloud

From ice cream to chocolate-covered strawberries, find your next favorite sweet treat at a local bakery or dessert shop.

The Stained Glass Lady St. Cloud

Women-Owned Businesses in Downtown St. Cloud

Discover female-owned businesses in this Central Florida town, including clothing boutiques, trendy shops, and local eateries.

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.

Shopping Local at Downtown St. Cloud Monthly Market

The Downtown St. Cloud Monthly Market is a can't-miss event in Central Florida where locals and visitors gather to enjoy live music, browse local vendors, and try delicious eats.

A sunny tree-lined street with colorful homes and businesses in Kissimmee, Florida.

Celebration, Florida: A Town Like No Other

With tree-lined streets, captivating architecture, and a welcoming mix of shops and restaurants, Celebration invites visitors of all ages to explore.

Couple walks through Universal Orlando Resort, smiling and waving near the iconic globe entrance. — Enjoy a sunny day exploring Universal Orlando Resort, one of the most thrilling and unforgettable attractions near Kissimmee, Florida.

A to Z in Kissimmee

Written by the

Two people hold hands outdoors, with a diamond engagement ring visible against a softly blurred green background. — A quiet moment of connection, where love takes center stage before the journey ahead.

Why Kissimmee is the Perfect Pre-Honeymoon Destination

Wedding planning can be stressful, which is why many couples are escaping for a pre-honeymoon getaway. Discover why Kissimmee, Florida, is the perfect destination for romance, relaxation, and adventure before the big day.

Two knights sword-fighting on the backs of horses at Medieval Times Dinner & Tournament — Catch a showtime of Medieval Times Dinner & Tournament

Epic Feasts & Battles at Medieval Times Dinner & Tournament

Step into the castle, feast like royalty, and watch an epic battle of gallant knights and old-world chivalry at Medieval Times Dinner & Tournament.

Two drinks in plastic cups are on a white table with a greenery background. The ube drink on the left is light purple with darker purple swirls and is topped with a glazed ube doughtnut and white icing. The peanut butter drink on the right is light brown with chocolate swirls and is topped with a glazed doughnut covered with crumbled peanut butter cups and a straw. — Ube and peanut butter cup beverages at Everglazed Donuts and Cold Brew.

Everglazed Donuts and Cold Brew in Kissimmee for the Perfect Sweet and Bold Experience

Indulge in the perfect combination of fresh doughnuts and smooth cold brew at Everglazed Donuts and Cold Brew in Disney Springs. Enjoy unique flavors, local ingredients, and an unforgettable experience.