Waterfront Restaurant
111 S. Bay Blvd
A cottage dining room with outdoor seating a few steps from the Historic City Pier, looking east across Tampa Bay toward the Sunshine Skyway. One of the north end's steadier dinner reservations.
Upscale
Island Guide
The island's kitchens run from sand-floor casual to a genuine fine-dining room, and almost all of them are within a short bike ride of the water.
A working list, not a ranking: the places that hold up year after year. Hours and menus change constantly on a seasonal island, so confirm before you drive over.
111 S. Bay Blvd
A cottage dining room with outdoor seating a few steps from the Historic City Pier, looking east across Tampa Bay toward the Sunshine Skyway. One of the north end's steadier dinner reservations.
Upscale
100 Spring Ave
Gulf-front dining directly on the sand, known for fresh local catch and a deck that fills for sunset. A long-running island institution and a frequent choice for beach weddings.
Mid-range
902 S. Bay Blvd
Sushi and Japanese cooking with marina views on the bay side, the island's alternative when grouper fatigue sets in.
Mid-range
Holmes Beach Paradise Plaza
A long-standing island pier kitchen, currently operating from Paradise Plaza. Simple fried and grilled seafood in an unpretentious room.
Casual
6600 Gulf Drive
The island's fine-dining benchmark: a small Gulf-front room with a serious wine list and a tasting-menu sensibility. Reservations are effectively required in season.
Upscale
5808 Marina Drive
A family-run tavern of four decades, locally regarded for its burgers and for staying exactly as it is. Cash-and-character rather than water views.
Casual
200 Gulf Drive
Gulf-front dining on the sand at the south end, known for grouper sandwiches and regular dolphin sightings offshore during dinner service.
Mid-range
121 Bridge Street
Seafood served in a restored 1920s cottage on Bridge Street, with live music on weekends and a porch that suits a long lunch.
Mid-range
900 Gulf Drive
Beach-casual all day, breakfast through dinner, with a tiki bar on the sand for the hours in between.
Casual
Thinking about buying here? Talk to Justin