Find Dining, Shopping and Outdoor Fun on a Kissimmee, Florida Weekend Escape

If you’re in Kissimmee, Florida, there’s a good chance you’re probably here for one of the theme parks, whether the one with the magical mouse, the one based on all the movies or any of the specialty destinations throughout the area. But there are also quite a few other attractions worth exploring in this convenient central Florida city.

Ahead, we’re naming some of the best non-theme-park activities in a weekend-long itinerary, covering everything from dining and shopping (you’ll want to head to the Historic Downtown) to outdoor recreation (lakes and Everglades galore). You might just be surprised at how much there is to do in this Orlando-adjacent city.

As always, check for travel restrictions and closures before planning your trip.

Friday: Visit the Historic Downtown

For your first morning in the area, tap into Kissimmee’s past by exploring its Historic Downtown neighborhood, where locals hang out, dine and shop. Start with breakfast at Susan’s Courtside Café, which serves a deliciously wide range of coffees and all of the classic baked goods.

Once you’re fueled up, meander down Main Street and peek into its historic buildings, most of which are now restaurants or shops. If you’re in the mood for antiquing, visit Lanier’s Historic Downtown Marketplace. There are also specialty shops like Lewis Music Store, House Rules Gaming (board games, card games and more) and Awakened Auras Co. (crystals and wellness-focused products).

For lunch, break for a quick slice or two at Broadway Pizza Bar or Main Street Pizza, then continue your tour through the neighborhood. A must-see is the historic Osceola County Courthouse, the oldest continuously operating courthouse in the state of Florida. It first opened in 1890, so it’s no surprise the site is listed on the National Register of Historic Places.

On the quirkier side, there’s the Monument of States, which actually has a more somber purpose than its bright colors convey — it’s a symbol of American unity post-Pearl Harbor.

Before dinner, stroll along the shores of Lake Tohopekaliga, better known as Lake Toho, then head to Big John’s Rockin’ BBQ for slow-smoked meats in a music-themed space. After your meal, head to Abracadabra Ice Cream Factory for some late-night treats if you’re traveling with your family. If you’re an adults-only group, consider a night out at Miguelo’s Ultra Lounge.

Saturday: Explore Florida’s Famous Waterways

Enjoy a classic breakfast at Kissimmee Diner this morning, and make sure it’s a substantial one — you’ll be spending your whole day outdoors. After breakfast, do your future self a solid and grab to-go sandwiches from Paul’s Italian Deli & Restaurant before heading out on the water.

If you’re in the mood for a more relaxed adventure, consider a fishing trip on one of Kissimmee’s many lakes — like Lake Toho, which is known for its abundant bass. If you go this route, you can either head off on your own or book a fishing tour and break for lunch at your leisure.

But if you’re craving a little more excitement, consider hopping on an airboat or Jet Ski tour of the headwaters of the Everglades through a company like Spirit of the Swamp Airboat Rides, Boggy Creek Airboat Adventures or 407 Jet Ski Rentals. In either case, you’ll have ample opportunities for wildlife spotting, from birds to gators.

For dinner, visit Mizu Japanese Steak House & Sushi. Don’t be put off by its unassuming strip-mall location — it’s good fun nonetheless, and the menu is massive. Bonus point: Entertain the kids with a hibachi-style meal.

Post-dinner, it’s time for ice cream (head back downtown to Limbhelados) or perhaps a cocktail or two at Breeze Kissimmee. There are daily drink specials, and they host trivia and other themed nights. You really never know what you’re going to get when you step inside — and we mean that in the best way possible.

Sunday: Golf in the Morning, Attractions in the Afternoon

For your last day in Kissimmee, take your breakfast at Woodsby’s Countryside Café, a rustic-style diner with hearty portions the locals line up for: stacks of pancakes, four-egg omelets, biscuits and gravy — the list goes on.

From here, grab your clubs and hit the links at one of Kissimmee’s golf courses, from the Rees Jones-designed Falcon’s Fire to the Arnold Palmer-designed Legends at Orange Lake. If you’re traveling with children, one of the mini-golf courses in town might be a better fit: Check out Congo River Golf or Mighty Jungle Golf.

Adults might want to have lunch at the golf club, but otherwise, we recommend dining at El Tapatio Mexican Restaurant, a casual joint with a lively atmosphere (and the occasional live music act). Order a plate full of tacos before an afternoon of history lessons. You’re off to explore two of Kissimmee’s non-theme-park attractions, both of which are popular with history buffs.

First up is the Museum of Military History, where you can take in hundreds of donated military artifacts — from the Revolutionary War to the Spanish-American War — from veterans around the world. Follow up your visit with a stop at the Pioneer Village at Shingle Creek, where historic structures from across Osceola County have been relocated to be preserved, including a Seminole settlement.

For dinner, you have a tough choice to make: Pay a visit to the Fox & Hounds Public House for classic pub food, the Italian Joint for — you guessed it — Italian fare or Better U Dining for Caribbean cuisine. Toast to the trip with a nightcap at the nearby 3 Sisters Speakeasy, where you can also take in some live music, if you’re lucky.