505 Fleet does it regularly with both trucks and containers. There is a container/truck every year from the east to west or vise versa for the North Americans, as well as multiple containers to the worlds from US.
Good article in SW about the Vipers and how they consulted with our shipping Guru to get boats to their worlds in Bermuda
Speaking of which a container (or two) could/should be going from the west coast to MA and back in June for the NAs. Given that the Worlds are also on the east coast in September there may not be too many takers so there may be room in any trucks/containers going back and forth.