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 76 results

11 - 20 of 76 results

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 bartender pours a beer at Celebration Brewing Co. — Enjoy a crisp beer at Celebration Brewing Co. in Celebration, Florida.

Local Spots in Downtown Kissimmee & St. Cloud

Explore downtown Kissimmee and St. Cloud for local boutiques, elevated bars, and entertaining nightlife in Central Florida.

ICEBAR Orlando: Unique Nightlife Experience

At ICEBAR Orlando, discover a winter wonderland in Florida, complete with ice sculptures, ice furniture, and ice cocktail glasses.

Pouring red wine into a flute from a bottle next a to a flute of white wine

Top Date Night Restaurants in Kissimmee

Add global flair to your date night and let your taste buds lead you on a delicious journey at these romantic restaurants in and around Kissimmee.

Top Restaurants in Celebration

From freshly baked biscuits to gourmet charcuterie plates to refreshing ice cream, Celebration's restaurants are sure to please.

Girl in yellow dress takes photo in front of Monument of States in Downtown Kissimmee. — The Monument of States in Kissimmee, Florida, a colorful, tiered structure made of stones, plaques, and items representing all American states.

A Local’s Guide to Historic Downtown Kissimmee

See Downtown Kissimmee's top historical buildings and sites during your visit.

The exterior of Breeze, a restaurant with an open-air patio partially hidden by tropical plants and palm trees, with guests seated inside. — Pull up a chair and let the laid-back Florida breeze remind you why slowing down feels so good.

Outdoor Dining in Downtown St. Cloud

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Chicken and avocado arepa on a plate — Chicken and avocado arepa, Susana's Cafe. By Corey Woosley / Atlas Obscura

Recipe: Reina Pepiada, the Venezuelan 'Curvy Queen'

Named after a beauty pageant winner, this deceptively simple dish is a favorite in Venezuelan cuisine.

Bowl of sancocho — Sancocho, Perico Ripiao. By Corey Woosley / Atlas Obscura

Recipe: Sancocho, a Dominican Stew That Feeds a Crowd

To make sancocho, you’ll want a big pot, lots of helping hands — and plenty of mouths to feed.

Woman relaxing in pool

Relax and Recharge: Your Guide to Wellness in Kissimmee

Unwind and rejuvenate in Kissimmee with top resorts, serene outdoor experiences, and mindful activities. Discover the perfect balance of relaxation and adventure in Central Florida.