Nightlife in Casselberry

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With its exposed bricks, arched doorways, and dim lighting, The Wine Room on Park Avenue evokes a medieval monastery. That may be why the sleek, Italian-made Enomatic wine dispenser, which controls bottle temperature and prevents oxidation, looks so much like a Star Trek–era gadget within the pleasantly rustic walls. With the push of a button, the metallic nozzles pour out precise 1-ounce sample-size, half-glass, or full-glass portions. To ensure spouts remain untainted from customer to customer, it cleans itself after every pour.

The Enomatic is one reason The Wine Room earned the title of Orlando's best wine bar from Orlando Magazine. The recently remodeled space now boasts additional seating, a new menu, and a new lineup of machines. Though the technology is impressive, the shop backs up their gadgetry with a staff of actual human wine connoisseurs. These friendly staffers help customers navigate the selection of 156 wines, and offer wine classes throughout the year. They can also recommend bottles to pair with The Wine Room's selection of cheeses, flatbreads, and yachts in need of christening.

270 S Park Ave
Winter Park,
FL
US

Amid the melodies of nightly karaoke, Devaney's marries hearty pub fare with daily drink specials. Signature cocktails and beer—from breweries including Bell's, Lagunitas, Victory, and Stone—wash back burgers, sandwiches, and wings. A surfeit of sports décor represents various teams battling on the flat-screen TVs, which beam down on tabletops and bar seating filled with patrons cheering as their favorite mascot executes a perfect high-five. The bar further engages crowds with Wednesday-night bingo, Thursday-night trivia, and weekly live bands, who are only sometimes possessed by ventriloquist dummies.

7660 University Blvd
Winter Park,
FL
US

A sea of framed snapshots of famous players sweeps across the newly painted wall of Friendly Confines. Sports games play on the dining room's numerous television screens, accompanying plates of hearty wings, burgers, and steaks. Outside, pint glasses, pitchers, and cocktail glasses clink beneath the colorful umbrellas that speckle the front patio. Throughout the week, the pub hosts games and contests, including Tuesday night bingo, Sunday night live music, and Wednesday afternoon competitive quilting.

3088 Aloma Ave
Winter Park,
FL
US

1566 W Fairbanks Ave
Winter Park,
FL
US

Bosphorous Turkish Cuisine is a family owned business, established in 2005, that offers variety of authentic Turkish food from many regions of Turkey. Bosphorous Turkish Cuisine adapted its name from one of the oldest cities in the world, Istanbul, which was once known as the Constantinople in the early 13th century.

108 S Park Ave
Winter Park,
FL
US

Corona Cigar Co. welcomes all types of cigar lovers, from casual smokers to rolled tobacco connoisseurs to four-star generals in need of chomping sticks. The shop’s friendly atmosphere encourages ample browsing, which is made easy by a stock of millions of premium in-store cigars that patrons can savor as they sit back, relax, and enjoy a rare spirit, cocktail, or glass of wine at the bar.

1130 Townpark Ave
Lake Mary,
FL
US

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Casselberry Restaurants

A comprehensive guide to restaurants, bars and more.