Edit
As of 2013, most links below are not functional anymore. However, I’ve found the cited paper, algorithm included, still available at this (very slow) server.
Here you can find a project dealing exactly with your issues. Although it works primarily with an area “filled” by points, you can set it to work with a “perimeter” type definition as yours.
It uses a k-nearest neighbors approach for calculating the region.
Samples:
Here you can request a copy of the paper.
Seemingly they planned to offer an online service for requesting calculations, but I didn’t test it, and probably it isn’t running.
HTH!