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Five Reasons to Visit Old Town in Kissimmee, Florida

  • By Christopher da Costa
  • Published 27 August 2019
  • Revised 25 September 2023
Five Reasons to Visit Old Town in Kissimmee, Florida
  • By Christopher da Costa
  • Published 27 August 2019
  • Revised 25 September 2023
Five Reasons to Visit Old Town in Kissimmee, Florida
  • By Christopher da Costa
  • Published 27 August 2019
  • Revised 25 September 2023
Take a trip back in time and experience small-town USA. At Old Town in Kissimmee, the crowds are small, the queues are short, and the fun is bigger and better for it. 

Located just 3 miles from the gates of Walt Disney World, this venue has undergone a multi-million dollar expansion in recent years. Featuring family-friendly rides like an 86-foot-high Ferris Wheel, iconic arcade games, authentic Floridian shops, and weekly festivals like classic car shows – there’s something for all ages to love.

Better yet, it’s completely free to enter Old Town! Sound fun? Learn more below, including our five favourite reasons to visit Old Town in 2024...

What exactly is Old Town Kissimmee?

Although it sounds like an area of Kissimmee, Old Town is an 18-acre complex that recreates the old-world charm of a classic Floridian town. In total, there are more than 60 unique shops and restaurants alongside the weekly festivals and timeless carnival rides. 

Five Our Our Favourite Old Town Experiences


Deciding between our favourite rides at Old Town is tough, but above all else, these nostalgic rides put the feels in thrills. 

The Ferris Wheel

First up, we love The Ferris Wheel. This hand-build ride was imported all the way from Italy and offers panoramic views as far as the eye can see. Each gondola seats six people and reaches a height of 86 feet. We recommend experiencing this attraction at night when more than 6,000 LED lights illuminate the wheel.

Happy Days Family Fun Center

There’s nothing quite like shared nostalgia to bring all ages together. At Happy Days, you can play classic arcade games of different generations, all the way up to the latest editions. All in all, there are more than 50+ video and skill games across this huge venue. Along the way, you can also enjoy cold drinks, hot food and sweet treats alongside top tunes. Better yet, from Thursday to Sunday, Happy Days also hosts contests and challenges that let you win some amazing prizes. 



Sometimes experiencing everything Kissimmee has to offer can be fun - yet tiring! So, if you’re searching for something a little slower or more relaxing, look no further…

Vivian’s Day Spa

Head to Vivian’s Day Spa and indulge yourself with a full body massage, facial, or even treat yourself to a manicure. After a few hours of pure relaxation, you’ll sure be ready to hit the rides again!

Groovy Store

At the Groovy Store, you can discover peace, love, and happy shopping. Funky fashion from the sixties and seventies is at your fingertips. Timeless t-shirts, jewellery and décor take you on a psychedelic trip that ends with you standing in line buying something for all the family.   

OT Barbershop 

Didn’t have time for a pre-holiday haircut? No problem. Enter the Old Town Barbershop for a trim, shave and hot towel treatment – all promised with personal attention to make you look and feel your best abroad. You can book your appointment through Booksy, with haircut prices starting from $18.



At Old Town, there’s a variety of weekly events both day and night. Here are a couple of our favourites for Kissimmee holidays in 2024

Saturday Classic Car Show & Cruise

Every Saturday, you can take a drive down memory lane. For over 30 years, the Old Tow Classic Car Show has delighted the young and old with the sight of show quality vintage cars. Today, 1985 or older hot rods, street rods and antiques are invited to cruise down to Old Town for the 1pm start of the show. The classic cars compete for weekly and monthly prize draws, and it’s completely free for you to watch. 

Old Town Karaoke

Holidays are all about letting loose, so how about a little bit of Karaoke? Whether you’re singing is good, bad, or mediocre, you are invited to Old Town’s Main Stage every Tuesday and Thursday. From 7pm – 11pm, you can enjoy your fifteen minutes of fame in a friendly and laid-back environment. 



By the time the sun sets and you’ve enjoyed most of what Old Town Kissimmee has to offer, finish your day off by enjoying a delicious sit-down meal at one of Old Town’s many restaurants…

Shoney’s Kitchen and Bar

After 70 years of happy customers, Shoney’s Kitchen and Bar know how to deliver great food for great value. From starting as a single drive-in in West Virginia, they now have 17 sit-down locations across the US, with their Old Town venue being a recent addition. Here, you can kick back in a casual dining setting and enjoy All-American food for breakfast, lunch, and dinner. 

Flippers Pizzeria

Perfecting pizza since 1987, Flippers Pizzeria serves “all natural ingredients with time-honoured artisan methods.” That means their chefs handcraft fresh dough daily, using unbleached artisan flour, extra virgin olive oil, all-natural meats and hand-picked spices – all baked to perfection in 600-degree brick ovens. Or in other words, it’s just the best pizza. Period. 



We couldn’t give a rundown on our favourite spots in Old Town without mentioning our favourite place for photos. At over 45 feet tall, the Jukeboxes at the entrance to Old Town epitomise what it’s all about. The colourful ’50s-style welcome signs have the “wow factor” and provide the opportunity to capture the perfect picture of Old Town as you arrive, letting you put your phone away early and leaving only good old-fashioned fun in the palm of your hands.

Ready for a Kissimmee holiday?

We have an array of villas beside Old Town, all with excellent on-site amenities that keep the fun rolling. Read our Ultimate Guide to the Best Villas in Kissimmee here or get in touch with our Travel Specialists today.

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