Sip and Savor: Local Drinks at Local Digs in Downtown Kissimmee

Thirsty for more than just a drink? Downtown Kissimmee’s bar scene delivers both flavor and charm, no matter what kind of night you’re after. Whether you're in the mood for a laid-back dive bar or an elegant wine lounge, there’s a perfect spot waiting for you. So grab your friends, raise your glasses, and get ready to sip your way through Kissimmee’s best local hangouts!

1881 Restaurant & Bar

Walk into 1881 Restaurant & Bar, and you’re stepping into a piece of Kissimmee history — served with a side of expertly crafted cocktails, of course! The Makinson Hardware building was the oldest operating hardware store in Florida after serving the community for an impressive 137 years. Today, 1881 Restaurant & Bar has breathed new life into this iconic space while preserving its historic charm.

The interior keeps Kissimmee’s heritage alive, featuring exposed brick walls and vintage photos celebrating the city’s cowboy culture. But while the setting pays tribute to history, the drinks are all about quality and creativity. 1881 takes mixology seriously, offering bold twists on classic cocktails and showcasing locally crafted spirits. Whiskey lovers, don’t miss Truitt’s Whiskey Old Fashioned, made with a small-batch whiskey from nearby St. Cloud. This sweet yet bold spirit delivers a taste of real Florida in every sip.

And what’s a great drink without some equally delicious bites? The 1881 Loaded Fries are a must-try, piled high with queso, smoky bacon, and house-made ranch. Perfect for sharing — though you might not want to after one bite!

• Drinks to check out:

  • The Smoky Kowboy: Yup, here in Kissimmee, we spell Kowboy with a ‘K.’ A local twist on the classic Paper Plane, this drink blends High West bourbon, lemon juice and Aperol, delivering smoky, citrusy flavors that nod to Kissimmee’s cowboy roots.
  • Warriors of Zenith: A fun take on a Moscow and Kentucky Mule, this drink features blackberry bourbon topped with ginger beer foam for a sweet, slightly spicy sip you’ll keep coming back to.
  • Just Try It: Not a gin fan? This drink is here to change your mind. Watermelon gin, Aperol, and fresh mint combine for a floral, dry, and refreshingly light cocktail. As its name suggests, you’ll just have to try it yourself!

Breeze Kissimmee

If walls could talk, Breeze Kissimmee would have some wild stories to tell. This one-of-a-kind bar is packed with personality — literally. Every inch of Breeze is brimming with character from the giant alligator skull to the zebra hide draped from the rafters. Keep an eye out for Norman, the bar’s decades-old talisman and unofficial mascot. But beyond the quirks, Breeze is also a tribute to the city’s past, with vintage maps and photos of influential locals making each corner a new story to discover over a cool drink.

Swing by Breeze in the afternoon, when locals gather for casual conversation and a round of pool. With two tables ready for action, you can put your skills to the test while sipping on an ice-cold beer.

If you’re in the mood to turn things up, Live DJs on Fridays and Saturdays keep the music pumping and the dance floor packed. And if you’ve had just enough liquid courage, step up to the mic for karaoke every Sunday. There’s no better way to make your night unforgettable than singing your favorite songs with a drink in hand and great company by your side.

• Drinks to Try

  • Kissimmee Lemonade:  A dangerously smooth mix of Tito’s vodka, watermelon sour mix, and Sprite for the ultimate refreshing sip to enjoy under Florida’s warm sun.
  • The Hell Shot: A bold combo of tequila and blood orange sour, the Hell Shot delivers just the right amount of heat to kick your night into high gear. 
  • Rumple Minze: A Breeze staple and local favorite, this German peppermint liqueur is crisp, refreshing, and guaranteed to take your breath away! 

Vintage Vino

Looking for a romantic night out? Or maybe just a quiet spot to unwind with good drinks and great conversation? Vintage Vino delivers on both, offering a cozy atmosphere that makes every visit feel like an escape. Owner and wine expert John Siudut is at the heart of the experience, greeting guests with a friendly smile and fascinating stories behind each bottle.

At Vintage Vino, enjoy a curated selection of wines, craft beers, and gourmet cheeses, with new additions weekly. Whether you're a wine enthusiast or just exploring, there's always something new to sip. And no wine experience is complete without perfectly paired cheese plates — the blueberry cheddar is a must-try! Each bite complements the smooth, rich wines that Vintage Vino is known for.

Beyond its inviting atmosphere and stellar selection, this wine bar is always hosting fun and unique events. If you love beer, don’t miss Craft Beer Night on Wednesdays, where you can sample handpicked craft beers from around the world. Wine Flight Night on Thursdays offers a guided tasting of three different wines that might just lead you to your next favorite bottle. Be sure to check out their monthly events, often featuring winemakers and sommeliers eager to share their expertise and passion.

• Drinks to Try

  • Sangue di Guida: This Italian gem is a lightly sparkling, semi-sweet red wine with rich berry flavors and a dangerously smooth finish.
  • Sean Minor Sauvignon Blanc: Crisp, refreshing and full of bright citrus notes, this is a perfect pick for white wine lovers.
  • Ayinger Celebrator Craft Beer: Craft beer lovers can’t miss out on this German Doppelbock, dark and malty with a smooth caramelized finish.