An optical transmission system includes an optical transmitting unit that outputs at least one optical signal having a wavelength included in an operation wavelength band and a holey fiber that is connected to the optical transmitting unit. The holey fiber includes a core and a cladding formed around the core. The cladding includes a plurality of holes formed around the core in a triangular lattice shape. The holey fiber transmits the optical signal in a single mode. A bending loss of the holey fiber is equal to or less than 5 dB/m at a wavelength within the operation wavelength band when the holey fiber is wound at a diameter of 20 millimeters.