A system and method are provided for connecting individuals for accompanied transportation. A method includes receiving input from a traveller, including transportation parameters, receiving input from a pre-authorised companion, including transportation parameters, and executes a transportation optimisation step including comparing transportation parameters and an assessment of one or more safety related parameters. The method then presents one or more optimised transportation proposal for acceptance by the traveller. Upon registering traveller selections and acceptance of the transportation proposal, the method notifies the traveller and selected companion and provides to the traveller or companion verification means prior to or at the accepted meeting time to enable verification of identities of the traveller or companion upon meeting. The method further monitors the safety related parameters to determine whether those parameters are satisfied and effects communication with the traveller or companion in response to the monitored one or more safety related parameters.