Kissimmee, Florida, may get on your radar because of its close proximity to the theme parks of Walt Disney World and Orlando, but this Central Florida gem deserves a guide all your own to get the most out of your Kissimmee vacation stay.

With a well-preserved history, quaint shops, and delicious eateries, Downtown Kissimmee gives visitors a charming look into small-town America. This is your insider’s tour of Kissimmee, Florida!

What to See in Downtown Kissimmee

Kissimmee Main Street Welcome Center

Photo Credit:

There’s no better place to acquaint yourself with Downtown Kissimmee than at the Kissimmee Main Street Welcome Center. Originally a filling station, this information hub now showcases artifacts from Kissimmee’s early years and offers a captivating glimpse into the stories and legends of the area’s historic buildings, so you’ll know what to keep an eye out for as you continue to explore the town on its quaint walking paths. 


Kissimmee Farmer’s Market

Kissimmee Farmer’s Market is the perfect place to visit for fresh, locally grown produce. Located in Downtown Kissimmee, this popular farmer’s market offers a wide selection of fruits and vegetables from local farms and vendors. 

Meet and support local farmers as you pick up the freshest fresh produce, as well as natural remedies, artisan soaps and creations, and other treats. Visit the first Friday of each month, from 5 pm to 8 pm.


Kissimmee Sculpture Experience

The Kissimmee Sculpture Tour is a free attraction that takes visitors through historic streets in Downtown Kissimmee, showing off its rich cultural heritage. During the tour, visitors can see dozens of original artworks donated by artists each year and landmarks like Florida’s oldest operating courthouse and the Monument of States.

Walk taking your art walk, keep an eye out for the splashes of color on walls all throughout downtown. The ARTisNOW project, a collaboration between Osceola Arts, the City of Kissimmee, Experience Kissimmee, and Sherwin-Williams, showcases colorful murals created by the local artists of Osceola County.


The Monument of States

Photo Credit:

Looking for an old and significant landmark in Downtown Kissimmee? Look no further than East Monument Avenue and Lakeview Drive! The Monument of States marker was built after the Pearl Harbor attack and included a rock from every state, inspiring American solidarity.

In 1943, countless donors from the community came together, and their names were etched in the concrete surrounding this city icon. You can even add to the story by taking a picture of yourself with the landmark and using the hashtag #MyKissimmee. Find your state’s rock and write a little bit of history!

Pro Tip: If you are in the mood for an easy stroll, head two blocks east of the city center to Kissimmee Lakefront Park. The perfect destination for sunrise or sunset along the walking path!


Shopping in Downtown Kissimmee


Photo Credit: Ground Picture

Lanier’s Historic Downtown Marketplace

Step into a treasure trove of antiques and collectibles at Lanier’s Historic Downtown Marketplace. This 18,000-square-foot antique mall in the heart of Historic Downtown Kissimmee is a must-visit for those looking to experience Central Florida’s hidden gems. Owned and operated by a family who knows their stuff, Lanier’s has been a fixture of the downtown area for over 13 years.

What’s more, they always keep a fresh pot of coffee brewing for shoppers so that you can stay caffeinated while you browse! Who knows what quirky souvenirs you might find?


Casa del Artesano

Casa del Artesano art gallery provides not only the chance to support local artists but also to have an interactive experience at one of their many workshops that double as educational sessions. Break up your shopping by stopping for lunch at the food truck in the back–or maybe even stop by in time for Friday night karaoke.

Awakened Auras

Awakened Auras is a heartfelt space that helps you connect with the energies within. Browse their collection of crystals, crystal jewelry, and other items meant to help you look within and find inner healing.


Where to Eat in Downtown Kissimmee

Photo Credit: Andrey Bayda

Broadway Pizza Bar

Get ready to indulge in Broadway Pizza Bar’s mouthwatering pizza and calzones, a local favorite that you simply can’t miss! Did you know that this building used to be an old Coca-Cola Bottling Company and a local bicycle shop before the owner bought it in 2008? Now, the interior has undergone a complete transformation, but you can still spot remnants of the past signage and catch a glimpse of historic Kissimmee photos while you wait for your steaming hot pizza to arrive. 

Plus, Broadway Pizza Bar is a friendly spot for those with allergies, as it offers gluten-free and vegan menu items. If you time your visit just right, you can swing by for their daily happy hour from 3-6 p.m.

Abracadabra Ice Cream Factory

Watch sugary magic come to life at the family-run Abracadabra Ice Cream Factory! Kids and families alike can’t get enough of the excitement. Using liquid nitrogen, Abracadabra freezes your custom creation in seconds, with temperatures reaching a mind-blowing 328 degrees below zero. 

Kids especially love watching the “Magic Clouds” flow across the countertop, creating a spectacle that’s sure to leave a lasting impression. As if that wasn’t family-friendly enough, Abracadabra also has bounce houses for kids 12 and under!

After mastering the art of ice cream, Abracadabra has now expanded into offering a full menu, including delicious appetizers, juicy Philly Cheesesteaks, mouth-watering burgers, and classic hot dogs.

The Italian Joint

The Italian Joint is a family-run restaurant that has delighted Downtown Kissimmee with its uncompromising passion for authentic Italian food. The friendly atmosphere welcomes you in as you enjoy some of their famous brick oven pizza. We’d suggest finishing off your meal with one of their cannolis! And afterward, visit the restaurant’s Italian Shop to pick up your own delicacies to take home.

Diane’s Tea Room

For a fancy addition to your day, stop by Diane’s Tea Room and Restaurant. This tea room is a family-owned establishment that offers a modern take on the traditional Victorian Tea Room. They provide a variety of over 40 tea options, sandwiches, and desserts for lunch, Sunday brunch, and special events like High Tea and Dinner. Enjoy pastries, scones, and other delicacies, all with a welcoming atmosphere.

Willy’s Wieners

A day out in small-town America calls for an all-American hot dog experience. Willy’s Wieners’ menu is extensive, starting with a classic Chicago-style hotdog and including almost any kind of dog you can think of. The combinations are endless, thanks to their wide variety of toppings to choose from. Go for a side of fried pickles or loaded beef fries if you’re feeling really hungry.

3 Sisters Speakeasy

This charming establishment is a hidden gem in the heart of Historic Downtown Kissimmee. The 3 Sisters Speakeasy offers a unique experience with its vintage décor and prohibition-era spirit. The speakeasy offers handcrafted cocktails and delicious hors d’oeuvres along with its retro vibe. 

Your visit might even coincide with some of their monthly events, such as the Antique Car Show (the last Friday of the month), Trivia Night Tuesdays (win a $50 gift card!), or live music (Wednesday through Saturday).

Vintage Vino Wine Bar

Located in the City’s Center of historic downtown, Vintage Vino Wine Bar offers an inviting atmosphere with its Tuscan-themed decor. Inside, you’ll find an array of over 50 fine wines and over 35 craft beers that can be enjoyed in the bar or taken home as a souvenir. They also offer a selection of cured meats and cheeses to round out the tasting experience. 


Spend the Day in Downtown Kissimmee

Whether you’re looking for a family-friendly outing, an educational tour, or some good old-fashioned Americana, Downtown Kissimmee won’t disappoint. Enjoy your time exploring all the delicious food and unique attractions this vibrant town offers while staying at a local vacation home!

Featured Image Credit: Pelow Media