The paper describes the design methodology, experimental validation and practical considerations of two millimeterwave wideband vertical transitions from two gap waveguide versions (inverted microstrip gap waveguide, and microstrip packaged by using gap waveguide) to standard WR-15 rectangular waveguide. The experimental results show S11 smaller than -10 dB over relative bandwidths larger than 25% and 26.6% when Rogers RO3003 and RO4003 materials are used respectively. The vertical transition from standard microstrip line packaged by a lid of pins to WR-15, shows measured return loss better than 15 dB over 13.8% relative bandwidth. The new transitions can be used as interfaces between gap waveguide feed-networks for 60 GHz antenna systems, testing equipment (like Vector Network Analyzers) and components with WR-15 ports, such as transmitting/receiving amplifiers. Moreover, the paper documents the losses of different gap waveguide prototypes compared to unpackaged microstrip line and Substrate Integrated Waveguide (SIW). This investigation shows that in V-band the lowest losses are achieved with inverted microstrip gap waveguide.