Five Nine Grill & Tavern expanding to Osprey

Five Nine Grill & Tavern, a Cortez Road staple in Bradenton, is heading south with a new Osprey location taking over the former Bay Leaf spot in Blackburn Point Plaza. Co-owner Mike DeGirolamo plans to reshape the roughly 3,000-square-foot space into a 120-seat restaurant, with most of the construction centered on rebuilding the bar. The new location will lean into a brunch, lunch, and dinner concept, likely opening around 9 or 9:30 in the morning to serve breakfast — a shift from the original Bradenton spot's format. It's a sign of the restaurant's growing footprint across the region as it brings its menu to a part of Sarasota County that hasn't had it before.