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Q. We’re expecting 20-something houseguests who like to explore the bar scene. Where should I send them? Believe it—there is a singles scene in Sarasota, and it’s centered on what I dub the Hillview corridor. Running west from the intersection of Hillview Street and U.S. 41 and extending north and south of Osprey Avenue, a […]


Q. We’re expecting 20-something houseguests who like to explore the bar scene. Where should I send them?

Believe it—there is a singles scene in Sarasota, and it’s centered on what I dub the Hillview corridor. Running west from the intersection of Hillview Street and U.S. 41 and extending north and south of Osprey Avenue, a string of hip restaurants and bars includes Peruvian, Middle Eastern, Asian, New American offerings and more. Mesa Lounge is a new addition to The Table and focuses on drinks with a Caribbean accent, in line with the south-of-the-border theme running through the menu. The décor is a bit more like South Beach, though, with contemporary seating and billowing drapery. The crowd is definitely in your guests’ age range. Fred’s offers more classic bar decor, and the crowd tends to be older but still handsome—and hip. At the corner of Hillview and Osprey is Sam Snead’s, the tamest of the three but definitely a player. After things quiet down on the restaurant side, the bar keeps going strong. Finally, the Five O’Clock Club is a mainstay in Sarasota and offers a blend of live, gritty blues and jazz.

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