Longboat Key offers Gulf to Bay living with deep water dockage in many locations for both Single Family Homes and Condominiums. The free Island Trolley provides transportation north to Anna Maria Island and south to Lido Key and St. Armand’s Circle shops & dining. As much an international destination as it is a beloved favorite among visitors and residents from all over. This magnificent length of shoreline got its first road courtesy of circus magnate John Ringling in 1925. Originally, it extended only from New Pass at the southernmost tip to the Manatee County line, but Ringling envisioned a beautifully landscaped boulevard that would run the full length of the barrier island. Longboat Key is ranked the safest small city in Florida.