Food lovers in Venice, Nokomis and Osprey now have a new spot to explore with the arrival of Five Nine Grill & Tavern, the popular Bradenton restaurant known for its elevated comfort food, welcoming atmosphere and scratch-made Southern-inspired specialties.
Situated in the former Bay Leaf space at Blackburn Point Plaza on South Tamiami Trail, the new location marks Five Nine’s first expansion into South Sarasota County.
For co-owner Mike DeGirolamo, the move into Osprey felt like a natural next move. “We always liked the area,” DeGirolamo said of Osprey, Nokomis and Venice. “It just seemed like a really good fit for our clientele.”
DeGirolamo, a Bradenton native, has spent roughly 35 years in the restaurant business, working with both corporate restaurant groups and independent concepts throughout Florida and the Midwest. Five Nine Grill & Tavern grew out of a desire to create something more personal alongside his wife, Holly, and business partner Quincy Watkins.
Today, the restaurant has developed a loyal following thanks to its combination of casual tavern energy and elevated comfort food.
“We’re not a sports bar,” DeGirolamo explained. “We’re a restaurant that you can watch sports in if you want.”
The expansive menu blends New American tavern fare with Southern comfort classics, seafood dishes, steaks, burgers and bowls—much of it prepared from scratch. Popular menu items include cheeseburgers, French dip sandwiches, jambalaya, shrimp and grits, Tuscan salmon bowls and Midwestern-style pork tenderloin sandwiches.
The restaurant’s scratch-kitchen philosophy remains central to the concept. “If we’re frying something, we’re hand-battering it,” DeGirolamo said.
Five Nine has also become a favorite among gluten-free diners because many fried items are prepared using rice flour breading, allowing guests to enjoy dishes like fish and chips without sacrificing flavor.
The Osprey restaurant seats approximately 120 guests and features a full-service bar with martinis, handcrafted cocktails and local craft beers. Extensive renovations transformed the former restaurant space with updates to the dining room, bar and guest areas.
While the Osprey location features many of the Bradenton restaurant’s signature favorites, it also places a greater emphasis on brunch, now served daily beginning at 9 a.m. Guests can explore brunch selections including biscuits and gravy, omelets, shrimp and grits, and a fried green tomato omelet topped with pimento cheese.
Seasonal specials and rotating comfort-food favorites also remain part of the experience, with offerings changing throughout the year.
Beyond the menu, DeGirolamo said community involvement remains an important part of the restaurant’s identity. Five Nine regularly partners with local schools, youth organizations and animal shelters through fundraisers and special events.
Still, he believes the restaurant’s greatest strength comes down to hospitality.
“You can have good food,” DeGirolamo said, “but what sets us apart are the employees we have and the service we deliver.”