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This modern pedestrian crossing above a major local highway is part of Kissimmee's Parks and Recreation trails projects and is also part of Florida's coast to coast public trails system.

Kissimmee sits just south of Orlando, and with roughly 80,000 year-round residents, the town is no backwater hamlet. Its history dates to the late 1800s, when it was a small trading post founded by settlers on the banks of Lake Tohopekaliga. Like many Florida towns, it prospered during the land boom of the early 1900s. By the 1920s, Kissimmee had switched its focus to cattle ranching, citrus orchards and sugarcane. By the 1950s the little town had reinvented itself again, this time as a snowbird haven. Today, Kissimmee is often overshadowed by nearby Orlando and the theme parks in its vicinity. But the town is worth its own weekend away, with plenty of heart-thumping activities to keep an entire family engaged.

Take a Step Back in Time

Kissimmee’s Old Town is an ode to Old Florida with shops, dining and activities inspired by yesteryear. The 18-acre outdoor complex is perfect for strolling. Grab a pina colada at the Tiki Station (5770 West Irlo Bronson Memorial Highway, Kissimmee; 704.712.2279) or stop by El Borrego (5770 West Irlo Bronson Memorial Highway, Kissimmee; 407.507.6011; elborregofl.com) for chef-inspired dishes from the Yucatan Peninsula. The nightlife hotspot Sun on the Beach (5770 West Irlo Bronson Memorial Highway, Kissimmee; 407.397.0207) features live music and dancing. And don’t miss the hot rods and muscle cars in Old Town’s weekly classic car show and cruise.

Go Medieval

Kissimmee’s Medieval Times Dinner and Tournament (4510 West Vine St., Kissimmee; 407.396.2900; medievaltimes.com) is legendary throughout the state. Guests enter a replica of an 11th-century castle for a fast-paced dinner theater experience unlike anything else in the area. For two hours, knights joust and swordfight in the arena and fans are treated to dramatic displays of horsemanship and falconry. Dinner is classic tavern fare—baked chicken, roast potatoes—and the fun continues after the show in the Hall of Arms, when members of the court mingle with the crowd. Raise a goblet to the queen and be prepared for a hoarse throat from all the cheering.

A Luxury Hotel and More

The Gaylord Palms Resort and Convention Center (6000 West Osceola Parkway, Kissimmee; 407.586.0000; marriott.com) offers more than a luxurious place to sleep. The beautifully outfitted indoor space feels like a visit to a botanical garden with its carefully selected palm trees and tropical plants. There’s a fitness center, plus a full-service salon and spa—don’t miss the warm coconut milk body treatment. The resort also offers a three-acre water park with seven water slides and a surfing simulator plus a lazy river for relaxing. With on-site restaurants that include a steakhouse, a top-notch seafood venue and a Mediterranean-inspired eatery, there’s no reason to leave—not even for a big theme park nearby.

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