Date Night in Kissimmee and St. Cloud

Kissimmee and St. Cloud have quintessential, all-American downtowns and to some city folk, that might not scream date night. But after some exploring, what I initially thought might be a short and sweet list of date night ideas has turned into a rather long list. If you're ready to leave the hustle and bustle of theme parks and city life behind, you will be pleasantly surprised by what you find tucked away in these small towns.

Here are a few itineraries for a memorable date night in with things to do in Kissimmee or St. Cloud. You can also explore these nature parks near the theme parks.

Updated by Beth Bell 2023

Adventurous Things to Do Kissimmee St. Cloud

While downtown St. Cloud and Kissimmee are perfect date night spots, there are also plenty of great places you can go for an outdoorsy day date! Grab breakfast at one of these fun spots around town, and make wild Florida your playground for a day.

In St. Cloud:

Rise before the sun and head to Sunshine Balloon Rides for a scenic hot air balloon ride over Central Florida. If you're still craving adventure, head to Wild Willy's Airboat Tours or for an exhilarating journey through the headwaters of the Everglades. 

Prefer something a little more laid-back? Charter a fishing boat and spend the day on the lake with Captain Bill Whipple of Lake Toho Fishing Company. Make a pit stop at Mick Farms, a family-owned u-pick and market stand where you can pick your own fresh strawberries and seasonal produce, or snag some farm-fresh finds to use in your next at-home dinner date.

Finally, end the day at Peghorn Nature Park & Trail, a eco-heritage site where you can explore a pioneer village and hike through wild Florida wetlands. At the trailhead, you'll find a visitor center, which was built in 1909, plus a blacksmith, schoolhouse, cannery, and barn. Keep an eye out for eagles, herons, turtles and butterflies along the wetland trail!

When it's time to fuel up, head over to Vanessa’s Coffee Shop, where you'll find savory omelettes, sweet stuffed french toast, and fun, eye-catching drinks like the café-coquito Nutella-coconut latte. These colorful dishes are sure to delight your eyes as well as your taste buds, and they're perfectly sized for sharing!

Frozen Banana Nut latte with added Nutella-Graham Cracker topping
Frozen Banana Nut latte with added Nutella-Graham Cracker topping | @vanessascoffeeshop


Another great alternative is Loading…Gastrobrunch in the historic Hunter Arms Hotel. Dig into playful dishes like breakfast waffle tacos (waffle cone shells served with chicken, candied bacon, sriracha maple syrup, cheddar jack, and eggs) or the Brittle Piggie, a full half pound of candied pepper bacon served with brittle dust and sriracha maple syrup. Loading… is a great date night spot as well, with dinner service on Tuesdays and Fridays, and themed mixology workshops throughout the year.


In Kissimmee:

Start your day at Shingle Creek Regional Park, the gateway to Lake Okeechobee and the Florida Everglades. Here, you can join a guided kayak eco-tour, hike an elevated boardwalk trail, and travel back to the pioneer days at Mary Kendall Steffee Nature Preserve. You'll find another pioneer village here, featuring a schoolhouse, a church, a general store, and more authentic Florida settler buildings.

Kayaking Shingle Creek at The Paddling Center in Kissimmee
Shingle Creek | Image credit: Stephanie Patterson


Take a self-guided tour of the settlement, or visit on Saturday for guided tours at 10am and 12pm. Be sure to request a guided tour online at least two weeks in advance!

If you venture away from downtown, you'll find even more outdoor fun at some of the area's best amusement parks and attractions. Crush an aerial obstacle course at Orlando Tree Trek Adventure Park, see alligators and other wildlife at Gatorland, or make a splash at Island H2O water park, right in front of Margaritaville Orlando Resort, and next to Sunset Walk Promenade

And of course, you can’t call yourself a Floridian until you’ve taken an airboat ride and seen some gators! Boggy Creek Airboat Adventures offers rides for $35 for a half hour or $55 for an hour, plus options for private tours and sunset rides.

Fuel up at the downtown Kissimmee Valley Farmers Market, hosted on the first Friday of the month from 5-8pm. Or, head to Buchito Restaurant for traditional Cuban comfort food and cafe con leche with prime people watching on the patio.

Enjoy Some Local Kissimmee St. Cloud Restaurants

If you want to #livelikealocal, try out one of these classic “mom and pop” spots!

St. Cloud:

  • Fat Boy’s Bar-B-Q – Around since 1982, this place is packed every time I drive by, especially on the weekends. If you are brave enough to fight the crowds it is without a doubt worth it. 
  • Jimmy Bear’s BBQ – Find it just off the main drag in St. Cloud located in a small house. Order “The Bear” for a shareable meal with all the meats and fixins’.
  • The Catfish Place – This family-owned casual seafood restaurant serves up fresh Lake Okeechobee grouper and other native seafood staples, like catfish, gator meat, and even soft-shelled turtle.
  • Bella Roma Pizza – voted best pizza in Osceola County, this family-owned pizzeria features fresh, house-made pizza dough and sauce, finished in a wood-fired oven for the perfect bite.
  • Chimento’s – Family-owned and operated for over 35 years, this is a local lunchtime favorite (dinner too!). 
  • Sip N’ Dip Donuts – Honestly, you should always stop and get some of these donuts for next morning’s breakfast anytime you are out in St. Cloud. While I haven’t tried every variety, my go-to is the blueberry donut.

Jimmy Bears BBQ – Hannah Green



  • 3 Sisters Speakeasy – This restaurant is named after three sisters that operated a real speakeasy in Kissimmee during the Prohibition era. The restaurant also has a spacious outdoor patio.
  • Big John’s Rockin’ BBQ – Yet another hometown BBQ spot that is popular with the locals. If you plan to visit, keep in mind that they close early around 7pm.
  • Main Street Pizza – This casual, order-at-the-counter pizza joint is new to the Kissimmee Main Street neighborhood. However, it has great deals and a special menu item called pepperoni buns. These are a twist on the cinnamon bun, where extra pizza dough is stuffed with pepperoni and mozzarella before being rolled up and baked and served with marinara sauce.

3 Sisters Speakeasy Downtown Kissimmee
3 Sisters Speakeasy Downtown Kissimmee – Hannah Green

Walk Along the Kissimmee St. Cloud Waterfront

Downtown Kissimmee borders Lake Tohopekaliga (try pronouncing that one! locals often call it Lake Toho for short) and St. Cloud borders East Lake Tohopekaliga. Both offer nicely paved walking paths where you can take an early evening stroll as the sun sets. Add a lakefront walk to any of the other date itineraries, or pack a picnic and enjoy watching the boats go in and out of the marinas.

Kissimmee Lakefront Park – Stephanie Patterson


Crabby Bill’s is located at the St. Cloud marina and provides a truly breathtaking sunset view overlooking the marina. Once you are done eating, take a night walk out to Dan Tarrell Memorial Point to up the romance a bit more.

Crabby Bill's is also one of our favorite family restaurants in Orlando.

Alternatively, explore Kissimmee Lakefront Park for sunset views and a walk (or bike ride) along the paved pathways. There are plenty of picnic areas and covered tables on the pier, if you choose to bring your own picnic – supplement with mouthwatering macarons from La Fontaine French Macarons. Don't miss the Monument of States, an unusual 50-foot tower decorated with stones, plaques and mementos collected from 48 States. It was erected as a symbol of national unity after the attack on Pearl Harbor during WWII.

Kissimmee Lakefront Park. Image credit: Stephanie Patterson

Embark on a Progressive Dinner and Bar Crawl

Easily walkable downtowns can only lead to one thing: a progressive dinner and bar crawl. Both Kissimmee and St. Cloud have wonderful restaurants with bar options. Here are our recommendations, but feel free to do your own exploring and/or mix it up!

In St. Cloud:

Spend an evening restaurant-hopping in the St. Cloud Downtown Entertainment District. Start with beer flights at Phyre Brewery and Tavern, a 1940s pinup-inspired speakeasy and nanobrewery with plenty of small-town charm. Enjoy live entertainment on Fridays and Saturdays, then head to Brews N’ Blues for dinner, drinks, and live music (every Thursday – Saturday).

Brws & Blues St. Cloud – Hannah Green


I highly recommend the Beer Cheese N’ Pretzel, because the pretzel is humongous, and the cheese is the perfect kind of creamy. For dessert, order the the highly popular Because We Can, bacon dipped in chocolate with a caramel drizzle.


In Kissimmee:

Head to Main Street for Broadway Pizza Bar, a pizza joint with a casual, vintage ambiance and a cozy feel. I suggest sharing some garlic knots and one of their specialty New York-style pizzas. Finally, wander down to Abracadabra Ice Cream Factory where your custom made ice cream creation is frozen with liquid nitrogen right in front of you!

Also try: Matador Tacos & Tapas Bar for small plates, Coquitos Ice Cream & Cafe Shop for sweet treats

Get Active

Osceola County Stadium once served as the spring training grounds for the Houston Astros, and was recently home to the Florida Firefrogs baseball team. Today, the stadium is part of a training complex for the Orlando City SC. Catch soccer games, concerts, rodeos, and more throughout the year.

These days, the Silver Spurs Rodeo is probably the most popular activity in the area. The largest rodeo east of the Mississippi, the Silver Spurs Riding Club has been in Kissimmee since 1941, with several major events drawing crowds throughout the year. The biggest of these events is the annual Silver Spurs Rodeo, which features seven traditional rodeo events: bull riding, saddle bronc riding, bareback riding, steer wrestling, team roping, tie-down roping, and barrel racing, plus a Rodeo Day parade and annual Silver Spurs pageant.


Osceola County school kids even get the day off to celebrate Rodeo Day, in honor of the region's ranching and agricultural heritage. Rodeo Day festivities typically coincide with the Osceola County Fair, making February a great time to check out this unique and meaningful piece of Florida history.

Art & Culture

Art is everywhere you look in downtown Kissimmee and St. Cloud. At the heart of this colorful downtown revival is Osceola Arts, a performing arts theater and gallery intentionally located halfway between the two cities. Catch hilarious live productions like Mel Brooks' Young Frankenstein, Clue, and Cruel Intentions: A 90's Musical. See all upcoming shows here. Osceola Arts also hosts local youth theater groups, offers art and theater workshops, and showcases Central Florida artists via rotating art exhibits that are free to all visitors. Their goal? To make art accessible to all.

The foundation's mission is felt across St. Cloud and Kissimmee, where you can discover colorful murals and free art in public places. The ARTisNOW Public Murals project encourages community conversation in Kissimmee, and makes for a fun social media photo op! Snap some cute pictures downtown at the Greetings from Kissimmee mural (131 Broadway Ave), Toho Sunset (421 Broadway) and more.

See all Osceola Arts murals in Kissimmee here. Plus, discover a rotating selection of local art through the Art in Public Places project. Take a self-guided tour of the latest art on display at the Kissimmee City Hall, Hart Memorial Library, Buenaventura Lakes Library, West Osceola Library, and Veteran’s Memorial St. Cloud Library.

Finally, visit Amber Vickers at The Stained Glass Lady in St. Cloud for jaw-dropping art, supplies, and DIY workshops. For a fun hands-on date night, sign up for one of the shop's regular glass workshops, and create your very own glass masterpiece! Past and upcoming workshop projects include sun catchers, mosaics, fused glass art, and more.
Find more class details on Facebook.

Wine Down at Vintage Vino

Vintage Vino deserves its own spot on this list because when I visited it was really hopping on a Wednesday! Plus, the atmosphere and fun weekly events make you feel like you are somewhere in downtown Orlando rather than downtown Kissimmee. Every Wednesday is Craft Beer Night from 5pm-10pm, which the locals refer to as “beer church.” Craft beer is $1 off and often people will bring in a bottle of something new or different for everyone to sample. On Thursdays, they have wine flight night from 5pm-10pm.

Finally, they occasionally have special tasting events, from wine and cheese pairings to specialty wine or cocktail tastings. While these tastings are very affordable, they are also very popular. Follow them on Facebook so you do not miss out!

Look for fun upcoming events on the Kissimmee Main Street and St. Cloud Main Street Facebook pages.

All images by Hannah Green unless otherwise noted

Feature image credit: Kissimmee Main Street