I like using (open source and gui friendly) Quantum GIS to convert the shapefile to kml.
Google Maps API supports only a subset of the KML standard. One limitation is file size.
To reduce your file size, you can Quantum GIS’s “simplify geometries” function. This “smooths” polygons.
Then you can select your layer and do a “save as kml” on it.
If you need to process a bunch of files, the process can be batched with Quantum GIS’s ogr2ogr command from osgeo4w shell.
Finally, I recommend zipping your kml (with your favorite compression program) for reduced file size and saving it as kmz.