written by
Alex Velazquez

10 Fun Things to Do in Kissimmee at Night

kissimmee vacations free things to do travel travel tips 9 min read

Chances are you may think of Kissimmee, Florida as a lesser known city where everyone turns out the lights when the sun goes down and goes to bed compared to its sister, Orlando which offers round the clock entertainment and fun. Affectionately known as “Kowtown,” due to its rich origin from the cattle industry, you will find a plethora of fun-filled nightly escapades like beach-inspired nightclubs, dinner shows, lively entertainment, British pubs and so much more. This means you don’t have to drive to Downtown Orlando, Disney Springs, International Drive or Universal CityWalk in Orlando for a good time! Keep reading these 10 fun things to do in Kissimmee at night:

1. Medieval Times Dinner & Tournament | Perhaps you only know of Medieval Times indirectly from watching a frantic Jim Carrey as “Chip Douglas” ham it up as a jousting knight much to the chagrin of Matthew Broderick as “Steven Kovacs” in the 1996 dark comedy The Cable Guy (see introductory quote above). Why not travel back in time to the age of chivalry and experience the real deal for yourself? Billed as “North America’s #1 Dinner Show,” Medieval Times opened in Kissimmee way back in 1983 and today continues its legacy of offering “Epic Battles of Steel and Steed.” Highlights of Medieval Times, which is housed in a huge European-style castle, include a thrilling, two-hour medieval jousting tournament featuring six competing knights on horseback in the Grand Ceremonial Arena, an abundant “hands-on” four-course feast (featuring roasted chicken, herb-roasted potato and corn cobette) and even the live flight of the royal falcon, as well as the Hall of Arms, King’s Hall and Medieval Life Museum.

2. Breeze Whiskey Lounge | Specializing in whiskey and handcrafted blends, Breeze Whiskey Lounge can be found in historic downtown Kissimmee near both Vintage Vino (see No. 4) and 3 Sisters Speakeasy (see No. 7). Enjoy live entertainment and an inviting outdoor patio at Breeze Whiskey Lounge, which stays open until 12 AM on weeknights and 2 AM on Fridays and Saturdays.

3. Capone’s Dinner & Show | A lively extravaganza that offers fun for all ages, the award-winning Capone’s blends all of the best elements of Broadway-style musicals, comedy and action for a one-of-a-kind dinner show that will definitely be one of the highlights of your Kissimmee vacation getaway! Follow the sidesplitting antics of “Finger Salvatorio,” “Miss Bunny-June,” “Buggsy Moran,” “Miss Jewel” and other colorful characters as they navigate their way through the ruthless world of gangland Chicago in the early 1930s. In addition, enjoy an abundant Italian-American buffet full of such mouthwatering delicacies as pasta with red sauce and meatballs and deep-dish meat lasagna, along with a new meat carving station (featuring steak, pork tenderloin and turkey), fresh salad bar and unlimited beverages.

4. Vintage Vino | Ideally located in the heart of the bustling City Centre in Historic Downtown Kissimmee, Vintage Vino is a classy but laid-back wine bar that first opened its doors in 2009 and today features a great selection of wines, craft beer and gourmet cheeses. Vintage Vino hosts Craft Beer Night every Wednesday between 5 PM and 10 PM, Wine Flight Night every Thursday between 5 PM and 10 PM and Happy Hour every Friday between 5 PM and 7 PM featuring $4 wines and $4 draft beers.

5. The Fox & Hounds Public House | An authentic English pub that was established in 1984, Fox & Hounds offers great food and a nice selection of European ales, ciders and lagers. The menu at Fox & Hounds boasts such traditional British fare as fish & chips, bangers & mash, steak & kidney pie, sausage rolls, scotch eggs, mushy peas and shepherd’s pie. In addition, the draft beer lineup at Fox & Hounds features such favorites as Guinness, Bass, Boddingtons, Stella Artois and Strongbow. Decorated throughout with colorful British memorabilia and collectibles, Fox & Hounds is the perfect locale to watch English Premier League football matches as well!

6. The Ice Factory of Central Florida | Take a break from the sweltering Central Florida heat at “the coolest place” in Kissimmee – The Ice Factory! Conveniently located just off the Florida Turnpike at Exit 244, The Ice Factory welcomes everyone from first-time skaters to “seasoned professionals” and offers public ice skating, ice skating lessons (the Learn to Skate USA program is available for ages 4 to adult), youth and adult ice hockey, and speed skating (it’s home to Sunshine State Speed Skating Club). By the way, every Tuesday night is “Cheap Skate” at The Ice Factory with $8 admission (including standard rental skates).

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7. 3 Sisters Speakeasy | A delightful contemporary eatery located in downtown Kissimmee next to Vintage Vino (see No. 4), 3 Sisters Speakeasy features “delectable drinks and hors d’oeuvres” in the “zestful spirit of prohibition.” 3 Sisters offers an eclectic menu full of sushi, tacos and quesadillas, wings, burgers (including the half-pound “Build Your Own Bootlegger Burger”), sandwiches, flatbreads, salads and appetizers, along with a full bar, outside patio, live music in the evenings and regular trivia nights. Save room for one of the hearty desserts like the Brownie Bar Sundae or Bananas Foster Cheesecake.

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8. Studio Movie Grill | For a delightfully eclectic Florida movie theater experience, head out to the “dine-in-style” Studio Movie Grill (AKA SMG Sunset Walk), which is located just off Highway 192 and State Road 429 at Sunset Walk. Highlights of Studio Movie Grill – billed as “the most comfortable and technologically advanced cinematic experience” – include 1,100 custom luxury lounge chairs and recliners in 12 movie theaters boasting state-of-the-art digital projection, Dolby 3D, Q-SYS custom sound systems, a full-service bar that serves premium craft cocktails and a made-to-order American Grill menu (service buttons are available at every seat).

9. Island Grove Wine Company at Formosa Gardens | Just 1.5 miles from Walt Disney World Resort, this laid-back winery and bistro, which opened its doors in 2010, offers a pleasant respite from all the “hustle and bustle” along U.S. 192. Specializing in fine blueberry wines, Island Grove is a great place to chill out after a day exploring Central Florida attractions. Choose from a variety of delicious, 100 percent fruit and fruit-infused wines such as Berry Dry Blackberry, Black & Blue Dry Berry, Kinda Dry Blueberry, Sorta Sweet Blueberry, Backporch Peach, Crisp Green Apple, Sunshine State Berry Sangria, Tiki Tango Mango, Southern Strawberry, Rustic Raspberry and others. Open seven days a week, the premises include the winery, tasting room and gift shop.

10. Sun on the Beach | Seeking some cool beach vibes? With its lively atmosphere, beach-inspired décor and tropical cocktails, Sun on the Beach offers a little bit of the Florida Keys right smack in the heart of the Old Town shopping, dining and entertainment district! Billed as the “Hottest Spot in Kissimmee,” Sun on the Beach features a sit-down eatery, four bars, a large stage, dance floor and live entertainment nightly. Sun on the Beach signature cocktails include the Island Blue Margarita, Mai Tai, Mermaid Water, Hurricane, Beach Party, Strawberry Lemonade, Pool Party Punch and Lynchburg Lemonade. Take home a souvenir 64-oz. Fish Bowl to commemorate your wild time at Sun on the Beach!

BONUS: Manor Pro Wrestling Dinner Theater | Billed as “The Ultimate Fine Dining & Pile Driving Experience,” Manor Pro Wrestling Dinner Theater will provide your family and friends with outrageous “bonzo gonzo” Kissimmee vacation stories for years to come! Enjoy the best in local pro wrestling entertainment combined with delicious food from the Manor Kitchen as Manor Pro Wrestling takes traditional dinner show entertainment to the next level. Watch local pro wrestling legends like The Beast Kamelot, Hell Warrior Carrion, The Scarecrow, The Black Butler, Santana Americus, King Tony Da Black, Najasism, Rome, The Widowmaker, Chuckles and many others battle it out in the ring! The menu includes such delicacies as the “Head Lock” Tossed Green Salad, “Body Slam” Oven Roasted Chicken, “Drop Kicking” Vegetable Medley and “Super Splash” Redskin Garlic Mashed Potatoes.

BONUS: Drafts Sports Bar & Grill | An ideal gathering spot for family and friends, Drafts Sports Bar & grill expertly combines the popular concepts of gourmet burger bars and brew pubs. Enjoy an outstanding selection of specialty microbrews, draft and bottled beers, wines and specialty cocktails at Drafts, where you can also catch your favorite sports team on one of the high-definition flat-screen televisions. Don’t miss Karaoke Night at Drafts Sports Bar & Grill every Wednesday between 7 PM and 10 PM.

There’s No Shortage of Great Nightlife Activities in Kissimmee!
You’ll always find something fun to do in Kissimmee. And if you do feel like making a little trip up the road, also check out the best Orlando breweries and International Drive bars too! Ready for a Kissimmee vacation adventure? Start with the best deals on Kissimmee hotels and visit our travel blog for resort specials and ideas for other fantastic vacation activities.

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