Cycling holidays with guided tours are widespread for cyclists to explore new locations comfortably. Specialized operators offer all-inclusive packages and strive to make these experiences convenient for the riders. They achieve that primarily by operating from a limited choice of destinations and with restricted flexibility. Therefore, there is potential for a more flexible solution to explore new locations by bike. Examples of multisided platforms such as Airbnb and GetYourGuide showed disruptive potential in the tourism sector. Their platforms connect different user groups straightforward and nimbly. Further, cyclists take advantage of technology-enabled solutions to enhance their riding experiences. Although many solutions specialize in route planning and navigation or maintain extensive user networks, no platform currently connects cyclists for tour guiding.