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.

11 - 20 of 27 results

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.

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 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, Florida has countless shops just waiting to be discovered.

Bottles of raw natural honey from 3Beez Honey Farm in St. Cloud, Florida, displayed on a shelf with decorative bee charms tied around the tops. — Local flavor at its sweetest. 3Beez Honey Farm brings Florida sunshine to every jar with small-batch, raw natural honey crafted right in St. Cloud.

Shop Local Across Downtown Kissimmee and St. Cloud

Experience the enchantment of charming, local Downtown Kissimmee and St. Cloud shops. Immerse yourself in unique, community-rooted businesses, and discover the joy of supporting locally-owned shops in Florida.

Entrance to Orlando Vineland Premium Outlets

Complete Guide to Orlando Vineland Premium Outlets

Welcome to shopper’s paradise, where fashion fantasies come to life and luxury items are at your fingertips.

ICEBAR Orlando: Unique Nightlife Experience

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

The Stained Glass Lady St. Cloud

Women-Owned Businesses in Downtown St. Cloud

Explore Downtown St. Cloud's women-owned businesses. They provide a diverse range of services for locals and tourists including creating stained glass, unique clothing finds, and delightful, sweet treats.

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.

Downtown St. Cloud Monthly Market: Shopping Local

The Downtown St. Cloud Monthly Market is a lively community event held every fourth Wednesday of the month, where locals and visitors gather to enjoy live music, browse unique local vendors, and indulge in delicious eats — all in the heart of charming historic St. Cloud.

Woman relaxing on a massage table wrapped in a white towel, surrounded by soft lighting, flowers, and candles in a tranquil spa setting. — Unwind and recharge with a soothing spa experience in Kissimmee.

Bump Up the Fun with a Blissful Three-Day Babymoon in Kissimmee

Calling all moms-to-be! Plan the ultimate babymoon in Kissimmee with this three-day itinerary filled with relaxation, pampering, and gentle adventures. From spa treatments to scenic nature spots, discover why Kissimmee is the perfect destination for a blissful pre-baby escape.

Wrapped Christmas gift in front of Christmas tree in Old Town Kissimmee — Find unique gifts for everyone on your list at Old Town Kissimmee

5 Best Ideas for Unique Gift Shopping in Kissimmee

Get your happy holidays on with this gift guide for all your beloved friends and family. This guide takes the hard choices out of finding the perfect gift. We’ll have you singing a love song as you go along, shopping in a Kissimmee wonderland.