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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1 - 10 of 26 results

1 - 10 of 26 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.

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.

Two women and a man walk down the streets of Celebration Town Center holding shopping bags. — Enjoy world-class shopping, entertainment, and dining in Celebration.

Unique Shopping in Kissimmee

Kissimmee has countless shops just waiting to be discovered. So if you're looking for high-end, luxury items or specialty souvenirs, you can find them all here.

Entrance to Orlando Vineland Premium Outlets

Complete Guide to Orlando Vineland Premium Outlets

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Red Mustang on display during a car show at Old Town Kissimmee — Catch a car show at Old Town Kissimmee

Car Shows at Old Town Entertainment District

Experience the best Kissimmee car shows at Old Town Entertainment District, where classic cars, hot rods, muscle cars, and vintage vehicles shine every week with free admission — alongside family-friendly attractions, dining, and live music.

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.

A stylish entertainment venue with pool tables, a bowling alley, and large-screen TVs glowing under red and blue lights in Kissimmee, Florida. — Enjoy a night of friendly competition with bowling, billiards, and big-screen entertainment at this vibrant venue in Kissimmee.

Food, Fun & Games at Kings Dining & Entertainment

With good food, creative cocktails, and a range of games with a high-end spin, Kings Dining & Entertainment in Orlando makes for a fun afternoon or night out.