Auto generate waypoints for a map

I am working on a project where I need a function which generate way-points considering the obstacle in the area. For example, if a shoreline world-map is given and the requirement is to generate 100 way-points within manually given start and end way-point around Cuba. While generating the way-points I have to avoid the landmass of Cuba. It can be thought of generating specified number (100) of way-points within a specified start and end way-point considering the obstacle (landmass of Cuba is the obstacle here). \

[generated_waypoints]= function(start_waypoint, end_waypoint, number_of_waypoints, obstacle_map)

I have looked at Navigation section in Matlab Map toolbox, but the way-point generation function (gcwaypts) in Matlab is developed without considering obstacles. I appreciate any references or functions that might related to this are.