We applied a far-field technique to measure the surface plasmon propagation over a wide range of gap sizes in thin gold stripes. This is realized with a grating technique which allows the excitation and out coupling of surface plasmon polaritons (SPPs). With this method the intensity can be monitored before and after the gap. The observations show that the SPPs can transmit over gaps with a width of 1μm with a probability of about 40% for Au stripe-waveguides (7 µm width) at a wavelength of 780 nm. The transmission decays exponentially above a gap size of 1 µm. The results also demonstrate that the transmission has non-monotonic behavior for gap sizes smaller than 1 µm that we attribute to excitation of Fabry-Perot modes and resonant localized plasmons within the gap. The experimental results are supported by numerical simulations using a Finite-Difference Time-Domain (FDTD) approach.